KR20220013315A - Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- KR20220013315A KR20220013315A KR1020210082869A KR20210082869A KR20220013315A KR 20220013315 A KR20220013315 A KR 20220013315A KR 1020210082869 A KR1020210082869 A KR 1020210082869A KR 20210082869 A KR20210082869 A KR 20210082869A KR 20220013315 A KR20220013315 A KR 20220013315A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- formula
- membered
- independently
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 180
- 239000000463 material Substances 0.000 title claims abstract description 97
- 239000000126 substance Substances 0.000 claims abstract description 11
- -1 benzoquinazolinyl Chemical group 0.000 claims description 411
- 125000003118 aryl group Chemical group 0.000 claims description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 44
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 40
- 229910052805 deuterium Inorganic materials 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000005104 aryl silyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000000732 arylene group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000005549 heteroarylene group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000004306 triazinyl group Chemical group 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 11
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 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 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 8
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 7
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 7
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005107 alkyl diaryl silyl 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
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 133
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000002019 doping agent Substances 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 19
- 238000000151 deposition Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 230000000903 blocking effect Effects 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 0 Cc1c(*)c2c(*c3c(*)c(*)c(*)cc3-3)c-3c(*)c(C)c2c(*)c1C Chemical compound Cc1c(*)c2c(*c3c(*)c(*)c(*)cc3-3)c-3c(*)c(C)c2c(*)c1C 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 125000003373 pyrazinyl group Chemical group 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- 238000001771 vacuum deposition Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229940078552 o-xylene Drugs 0.000 description 10
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229940125782 compound 2 Drugs 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 4
- MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical group NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 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 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- 239000010409 thin film Substances 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
- AYJJTPLDSZAGGA-UHFFFAOYSA-N 2-ethyl-7-methyl-5-(4-methylphenyl)-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridine Chemical class C1N(CC)CCC2C1C1=CC=C(C)C=C1C2C1=CC=C(C)C=C1 AYJJTPLDSZAGGA-UHFFFAOYSA-N 0.000 description 2
- AZFABGHLDGJASW-UHFFFAOYSA-N 3-bromodibenzofuran Chemical compound C1=CC=C2C3=CC=C(Br)C=C3OC2=C1 AZFABGHLDGJASW-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical class C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical class C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 2
- FFYZMBQLAYDJIG-UHFFFAOYSA-N dibenzofuran-2-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3OC2=C1 FFYZMBQLAYDJIG-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004957 naphthylene group Chemical group 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
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- ZARCYQBIHIVLOO-UHFFFAOYSA-N pyridine;triazine Chemical compound C1=CC=NC=C1.C1=CN=NN=C1 ZARCYQBIHIVLOO-UHFFFAOYSA-N 0.000 description 2
- 239000002096 quantum dot Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- BHFOCYFMWUHOLQ-UHFFFAOYSA-N 1,2-dimethyl-11h-benzo[a]fluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC1=CC=C(C)C(C)=C12 BHFOCYFMWUHOLQ-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 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
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YAVCXSHORWKJQQ-UHFFFAOYSA-N 1-phenyl-2-(2-phenylphenyl)benzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 YAVCXSHORWKJQQ-UHFFFAOYSA-N 0.000 description 1
- OWPJBAYCIXEHFA-UHFFFAOYSA-N 1-phenyl-3-(3-phenylphenyl)benzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 OWPJBAYCIXEHFA-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- RJBGUYLSEAPCKK-UHFFFAOYSA-N 11-chloronaphtho[2,3-b][1]benzofuran Chemical compound ClC1=C2C=CC=CC2=CC=2OC3=C(C=21)C=CC=C3 RJBGUYLSEAPCKK-UHFFFAOYSA-N 0.000 description 1
- FWBYVQSBHTWZKR-UHFFFAOYSA-N 11-chloronaphtho[2,3-b][1]benzothiole Chemical compound ClC1=C(C=CC=C2)C2=CC2=C1C(C=CC=C1)=C1S2 FWBYVQSBHTWZKR-UHFFFAOYSA-N 0.000 description 1
- ZDPDDOIOIKNGEJ-UHFFFAOYSA-N 11h-indeno[1,2-h]quinoline Chemical class C1=CC=NC2=C3CC4=CC=CC=C4C3=CC=C21 ZDPDDOIOIKNGEJ-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
- FXHGBACNYDFALU-UHFFFAOYSA-N 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 FXHGBACNYDFALU-UHFFFAOYSA-N 0.000 description 1
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 1
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 1
- RTFPTPXBTIUISM-UHFFFAOYSA-N BrCc1cccc(-c2ccccc2)c1 Chemical compound BrCc1cccc(-c2ccccc2)c1 RTFPTPXBTIUISM-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- FFYGSGVSRLOXAI-UHFFFAOYSA-N C(C1)C=CC(C2=CC=CCC2)=C1C(Nc1ccc2cc3)Oc1c2c1c3ccc(N(c2ccccc2)c2cc(N(C3C=CC=CC33)c4ccccc4)c3cc2)c1 Chemical compound C(C1)C=CC(C2=CC=CCC2)=C1C(Nc1ccc2cc3)Oc1c2c1c3ccc(N(c2ccccc2)c2cc(N(C3C=CC=CC33)c4ccccc4)c3cc2)c1 FFYGSGVSRLOXAI-UHFFFAOYSA-N 0.000 description 1
- ZPDJKFYLZSZTJO-UHFFFAOYSA-N C(C1)C=CC=C1C1Oc(c2c(cc(cc3)N(c(cc4)ccc4-c4ccccc4)c4c(c(cccc5)c5[s]5)c5ccc4)c3ccc2cc2)c2N1 Chemical compound C(C1)C=CC=C1C1Oc(c2c(cc(cc3)N(c(cc4)ccc4-c4ccccc4)c4c(c(cccc5)c5[s]5)c5ccc4)c3ccc2cc2)c2N1 ZPDJKFYLZSZTJO-UHFFFAOYSA-N 0.000 description 1
- KBXKTBMIUNIREL-UHFFFAOYSA-O C(C1)C=CC=C1C1[OH+]c(c2c(cc(cc3)N(C(C4)C=CC(C5C=CC=CC55)=C4N5c4ccccc4)c4ccccc4)c3ccc2cc2)c2N1 Chemical compound C(C1)C=CC=C1C1[OH+]c(c2c(cc(cc3)N(C(C4)C=CC(C5C=CC=CC55)=C4N5c4ccccc4)c4ccccc4)c3ccc2cc2)c2N1 KBXKTBMIUNIREL-UHFFFAOYSA-O 0.000 description 1
- ZJAPOCHLOBHIAS-UHFFFAOYSA-N CC(C1c2c3[O-]C(C4=CC=CCC4)Nc3ccc2C=CC1C=C1)C1N(c(cc1)ccc1-c1ccccc1)c1c2[s]c3ccccc3c2ccc1 Chemical compound CC(C1c2c3[O-]C(C4=CC=CCC4)Nc3ccc2C=CC1C=C1)C1N(c(cc1)ccc1-c1ccccc1)c1c2[s]c3ccccc3c2ccc1 ZJAPOCHLOBHIAS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RBGKKWGFJCFMIA-UHFFFAOYSA-N Clc1cc(c2c3OC(C4=CCCC=C4)Nc3ccc2cc2)c2cc1 Chemical compound Clc1cc(c2c3OC(C4=CCCC=C4)Nc3ccc2cc2)c2cc1 RBGKKWGFJCFMIA-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 102100039856 Histone H1.1 Human genes 0.000 description 1
- 101001035402 Homo sapiens Histone H1.1 Proteins 0.000 description 1
- 238000003461 Miyaura Borylation reaction Methods 0.000 description 1
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XDNADZYPWVQFRI-UHFFFAOYSA-N [1]benzofuro[2,3-h]quinoline Chemical class C1=CC=NC2=C3C4=CC=CC=C4OC3=CC=C21 XDNADZYPWVQFRI-UHFFFAOYSA-N 0.000 description 1
- CWDFYKZZCSEOPO-UHFFFAOYSA-N [1]benzothiolo[2,3-h]quinoline Chemical class C1=CC=NC2=C3C4=CC=CC=C4SC3=CC=C21 CWDFYKZZCSEOPO-UHFFFAOYSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- MDLHEADEPQXWHI-UHFFFAOYSA-N benzene;furan Chemical compound C=1C=COC=1.C1=CC=CC=C1 MDLHEADEPQXWHI-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=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
- 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- LPGCEGCXRRKSSW-UHFFFAOYSA-N c(cc1)ccc1-c(c1c2c(cccc3)c3[s]1)c(cccc1)c1c2-c(cc1)ccc1-c1nc(-c(cc2)cc3c2c(cccc2)c2[o]3)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(c1c2c(cccc3)c3[s]1)c(cccc1)c1c2-c(cc1)ccc1-c1nc(-c(cc2)cc3c2c(cccc2)c2[o]3)nc(-c2ccccc2)n1 LPGCEGCXRRKSSW-UHFFFAOYSA-N 0.000 description 1
- LXOCTSJQHHCASE-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(Nc2cc(-c3ccccc3)ccc2)c1 Chemical compound c(cc1)ccc1-c1cccc(Nc2cc(-c3ccccc3)ccc2)c1 LXOCTSJQHHCASE-UHFFFAOYSA-N 0.000 description 1
- UPZPJZACVOGPIQ-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2c(cccc3)c3cc3c2c(cccc2)c2[o]3)nc2c(cccc3)c3ccc12 Chemical compound c(cc1)ccc1-c1nc(-c2c(cccc3)c3cc3c2c(cccc2)c2[o]3)nc2c(cccc3)c3ccc12 UPZPJZACVOGPIQ-UHFFFAOYSA-N 0.000 description 1
- GZLCEEIXUZIRLO-UHFFFAOYSA-N c1ccc(C(Nc2ccc3cc4)Oc2c3c2c4ccc(N(c(cc3)cc4c3c(cccc3)c3[o]4)c3cc(-c4ccccc4)ccc3)c2)cc1 Chemical compound c1ccc(C(Nc2ccc3cc4)Oc2c3c2c4ccc(N(c(cc3)cc4c3c(cccc3)c3[o]4)c3cc(-c4ccccc4)ccc3)c2)cc1 GZLCEEIXUZIRLO-UHFFFAOYSA-N 0.000 description 1
- DLNOHVPYRYLGJM-UHFFFAOYSA-N c1ccc(C2Oc(c3c(cc(cc4)Nc5cccc(-c6ccccc6)c5)c4ccc3cc3)c3N2)cc1 Chemical compound c1ccc(C2Oc(c3c(cc(cc4)Nc5cccc(-c6ccccc6)c5)c4ccc3cc3)c3N2)cc1 DLNOHVPYRYLGJM-UHFFFAOYSA-N 0.000 description 1
- XMQWRIVSFMZFCK-UHFFFAOYSA-O c1ccc(C2[OH+]c(c3c(cc(cc4)N(c(cc5)ccc5-c5ccccc5)c5ccc6[s]c(cccc7)c7c6c5)c4ccc3cc3)c3N2)cc1 Chemical compound c1ccc(C2[OH+]c(c3c(cc(cc4)N(c(cc5)ccc5-c5ccccc5)c5ccc6[s]c(cccc7)c7c6c5)c4ccc3cc3)c3N2)cc1 XMQWRIVSFMZFCK-UHFFFAOYSA-O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 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
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- PESBFNLGEMHNAM-UHFFFAOYSA-N n,n-bis(4-phenylphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 PESBFNLGEMHNAM-UHFFFAOYSA-N 0.000 description 1
- AFDFEVPHXYRVDH-UHFFFAOYSA-N n-(4-bromophenyl)-n,4-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 AFDFEVPHXYRVDH-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000007122 ortho-metalation reaction Methods 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- 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
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005415 substituted alkoxy group 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
- 230000036962 time dependent Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/10—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 two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본원은 유기 전계 발광 화합물, 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present application relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device including the same.
이스트만 코닥 사의 Tang 등이 1987년에 발광층과 전하 전달층으로 이루어진 TPD/Alq3 이중층 저분자 녹색 유기 전계 발광 소자(OLED)를 처음으로 개발한 이후, 유기 전계 발광 소자에 대한 연구가 급속도로 빠르게 이루어져 현재 상용화에 이르렀다. 현재, 유기 전계 발광 소자는 패널 구현에 있어 발광 효율이 뛰어난 인광 물질을 주로 사용하고 있다. 디스플레이의 장시간 사용과 높은 해상도를 위해서 높은 발광 효율 및/또는 장 수명을 갖는 OLED가 요구되고 있다.Eastman Kodak's Tang et al. first developed a TPD/Alq3 double-layer low-molecular green organic electroluminescent device (OLED) consisting of a light emitting layer and a charge transport layer in 1987. reached Currently, the organic electroluminescent device mainly uses a phosphor having excellent luminous efficiency in realizing a panel. OLEDs having high luminous efficiency and/or long lifespan are required for long-term use and high resolution of the display.
발광 효율, 구동 전압 및/또는 수명을 개선시키기 위하여 유기 전계 발광 소자의 유기층에 여러 재료들 또는 컨셉들이 제안되어 왔으나, 현실적으로 사용하기에는 만족스럽지 못하였다. 이에, 기존에 개시된 유기 전계 발광 소자에 비해 보다 개선된 성능, 예컨대 개선된 구동전압, 발광효율, 전력효율 및/또는 수명 특성을 갖는 유기 전계 발광 소자를 개발하는 것이 지속적으로 요구되고 있다.Various materials or concepts have been proposed for the organic layer of an organic electroluminescent device in order to improve luminous efficiency, driving voltage, and/or lifetime, but they are not satisfactory for practical use. Accordingly, there is a continuous need to develop an organic electroluminescent device having improved performance, for example, improved driving voltage, luminous efficiency, power efficiency, and/or lifespan characteristics compared to the previously disclosed organic electroluminescent device.
한편, 한국 특허공개공보 제2012-0104067호는 벤조나프토티오펜 모이어티에 질소 함유 헤테로아릴이 결합된 화합물을 개시하고 있으나, 본원에서 청구하는 특정 조합의 호스트 재료를 구체적으로 개시하고 있지 않다.Meanwhile, Korean Patent Laid-Open Publication No. 2012-0104067 discloses a compound in which a nitrogen-containing heteroaryl is bonded to a benzonaphthothiophene moiety, but does not specifically disclose a host material of a specific combination claimed herein.
본원의 목적은, 유기 전계 발광 재료로 사용하기에 적합한 새로운 구조의 화합물을 제공하는 것이다. 본원의 또 다른 목적은, 특정 조합의 화합물을 포함하는 복수 종의 호스트 재료를 포함함으로써, 낮은 구동전압, 높은 발광효율, 높은 전력효율 및/또는 우수한 수명 특성을 갖는 유기 전계 발광 소자를 제공하는 것이다.It is an object of the present application to provide compounds of novel structures suitable for use as organic electroluminescent materials. Another object of the present application is to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, high power efficiency and/or excellent lifespan characteristics by including a plurality of host materials including a compound of a specific combination. .
상기의 기술적 과제를 해결하기 위해 예의 연구한 결과, 본 발명자들은 하기 화학식 2' 또는 화학식 2"로 표시되는 유기 전계 발광 화합물이 상술한 목적을 달성함을 발견하여 본 발명을 완성하였다. 또한, 1종 이상의 제1 호스트 화합물 및 1종 이상의 제2 호스트 화합물을 포함하는 복수 종의 호스트 재료로서, 상기 제1 호스트 화합물은 하기 화학식 1로 표시되고, 상기 제2 호스트 화합물은 하기 화학식 2로 표시되는 것인, 복수 종의 호스트 재료가 상술한 목적을 달성함을 발견하여 본 발명을 완성하였다.As a result of intensive research to solve the above technical problem, the present inventors have completed the present invention by discovering that the organic electroluminescent compound represented by the following Chemical Formula 2' or Chemical Formula 2" achieves the above-described object. In addition, 1 A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula (1), and the second host compound is represented by the following formula (2) Phosphorus, a plurality of types of host materials, has been found to achieve the above object, thereby completing the present invention.
[화학식 2'][Formula 2']
상기 화학식 2'에서,In Formula 2',
HAr은 각각 독립적으로 치환 또는 비치환된 트리아지닐, 치환 또는 비치환된 피리딜, 치환 또는 비치환된 피리미디닐, 치환 또는 비치환된 퀴나졸리닐, 치환 또는 비치환된 벤조퀴나졸리닐, 치환 또는 비치환된 퀴녹살리닐, 치환 또는 비치환된 벤조퀴녹살리닐, 치환 또는 비치환된 벤조푸로피리미디닐, 또는 치환 또는 비치환된 벤조티에노피리미디닐이고;Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;Ar 11 is each independently any one of Formulas 3 to 5;
[화학식 3] [화학식 4] [화학식 5][Formula 3] [Formula 4] [Formula 5]
상기 화학식 3 내지 5에서,In Formulas 3 to 5,
Y2는 O 또는 S이며;Y 2 is O or S;
R20 내지 R29은 수소 또는 중수소이고;R 20 to R 29 are hydrogen or deuterium;
e는 1 또는 2이며, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있으며;e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
*는 L11와 연결되는 위치를 나타내고;* indicates a position connected to L 11 ;
단, HAr이 치환된 트리아지닐인 경우, 트리아지닐의 치환기는 각각 독립적으로 중수소, 페닐, 나프틸, 비페닐, 터페닐, 페난트레닐, 트리페닐레닐, 디메틸플루오레닐, 플루오란테닐, 크라이세닐, 카바졸릴 및 이들의 조합으로부터 선택되고, 치환기가 2개인 경우 이들은 서로 같거나 상이하다.However, when HAr is substituted triazinyl, the substituents of triazinyl are each independently deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, fluoranthenyl, cry senyl, carbazolyl, and combinations thereof, and when there are two substituents, they are the same as or different from each other.
[화학식 2"][Formula 2"]
상기 화학식 2"에서,In Formula 2",
HAr은 각각 독립적으로 치환 또는 비치환된 트리아지닐, 치환 또는 비치환된 퀴나졸리닐, 치환 또는 비치환된 벤조퀴나졸리닐, 치환 또는 비치환된 퀴녹살리닐, 치환 또는 비치환된 벤조퀴녹살리닐, 치환 또는 비치환된 벤조푸로피리미디닐, 또는 치환 또는 비치환된 벤조티에노피리미디닐이고;Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl , a substituted or unsubstituted benzofuropyrimidinyl, or a substituted or unsubstituted benzothienopyrimidinyl;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;Ar 11 is each independently any one of Formulas 3 to 5;
[화학식 3] [화학식 4] [화학식 5][Formula 3] [Formula 4] [Formula 5]
상기 화학식 3 내지 5에서,In Formulas 3 to 5,
Y2는 O 또는 S이며;Y 2 is O or S;
R21 내지 R24 및 R26 내지 R29은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;R 21 to R 24 and R 26 to R 29 are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R20 및 R25는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이며;R 20 and R 25 are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
e는 1 또는 2이고, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있으며;e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
*는 L11와 연결되는 위치를 나타낸다.* indicates a position connected to L 11 .
[화학식 1] [Formula 1]
상기 화학식 1에서,In Formula 1,
X1 및 Y1은 각각 독립적으로 -N=, -NR5-, -O- 또는 -S-이고, 단, X1 및 Y1 중 어느 하나는 -N=이고, X1 및 Y1 중 다른 하나는 -NR5-, -O- 또는 -S-이며;X 1 and Y 1 are each independently -N=, -NR 5 -, -O- or -S-, with the proviso that any one of X 1 and Y 1 is -N=, and the other of X 1 and Y 1 one is -NR 5 -, -O- or -S-;
R1은 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;R 1 is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
L1는 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;L 1 is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;Ar 1 and Ar 2 are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R2 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 또는 -L3-N(Ar3)(Ar4)이거나; 인접한 치환기끼리 서로 연결되어 고리를 형성할 수 있으며;R 2 to R 5 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L 3 -N(Ar 3 )(Ar 4 ); adjacent substituents may be linked to each other to form a ring;
a는 1이고, b 및 c는 각각 독립적으로 1 또는 2이며, d 는 1 내지 4의 정수이고, b 내지 d가 2 이상의 정수인 경우, 각각의 R2 내지 R4는 서로 동일하거나 상이할 수 있으며;a is 1, b and c are each independently 1 or 2, d is an integer of 1 to 4, and when b to d are an integer of 2 or more, each R 2 to R 4 may be the same or different from each other, ;
[화학식 2][Formula 2]
상기 화학식 2에서,In Formula 2,
HAr은 각각 독립적으로 치환 또는 비치환된 질소 함유 (3-20원)헤테로아릴이고;each HAr is independently a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;Ar 11 is each independently any one of Formulas 3 to 5;
[화학식 3] [화학식 4] [화학식 5][Formula 3] [Formula 4] [Formula 5]
상기 화학식 3 내지 5에서,In Formulas 3 to 5,
Y2는 O 또는 S이며;Y 2 is O or S;
R20 내지 R29은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 또는 -L3-N(Ar3)(Ar4)이고;R 20 to R 29 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L 3 -N(Ar 3 )(Ar 4 );
e는 1 또는 2이며, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있고;e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
*는 L11와 연결되는 위치를 나타내고;* indicates a position connected to L 11 ;
상기 화학식 1 및 3 내지 5에서,In Formulas 1 and 3 to 5,
L3은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;L 3 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar3 및 Ar4는 각각 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이다.Ar 3 and Ar 4 are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C3-C30) aliphatic ring; (C6-C30) is a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.
본원에 따른 유기 전계 발광 화합물은 유기 전계 발광 소자에 사용하기에 적합한 성능을 발휘한다. 또, 본원에 따른 복수 종의 호스트 재료를 포함함으로써, 종래의 유기 전계 발광 소자에 비해 낮은 구동전압, 높은 발광효율, 높은 전력효율 및/또는 우수한 수명 특성을 갖는 유기 전계 발광 소자가 제공되며, 이를 이용한 표시 장치 또는 조명 장치의 제조가 가능하다.The organic electroluminescent compound according to the present disclosure exhibits suitable performance for use in organic electroluminescent devices. In addition, by including a plurality of types of host materials according to the present application, an organic electroluminescent device having a low driving voltage, high luminous efficiency, high power efficiency and/or excellent lifespan characteristics compared to a conventional organic electroluminescent device is provided, It is possible to manufacture a display device or a lighting device using the same.
도 1은 본원의 유기 전계 발광 화합물의 대표적인 화학식이다.1 is a representative chemical formula of the organic electroluminescent compound of the present application.
이하에서 본원을 더욱 상세히 설명하나, 이는 설명을 위한 것으로 본원의 범위를 제한하도록 해석되어서는 안 된다.DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present application is described in more detail below, but it is for illustrative purposes only and should not be construed as limiting the scope of the present application.
본원에서 "유기 전계 발광 화합물"은 유기 전계 발광 소자에 사용될 수 있는 화합물을 의미하며, 필요에 따라 유기 전계 발광 소자를 구성하는 임의의 층에 포함될 수 있다.As used herein, "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device, and may be included in any layer constituting the organic electroluminescent device, if necessary.
본원에서 "유기 전계 발광 재료"는 유기 전계 발광 소자에 사용될 수 있는 재료를 의미하고, 1종 이상의 화합물을 포함할 수 있으며, 필요에 따라 유기 전계 발광 소자를 구성하는 임의의 층에 포함될 수 있다. 예를 들면, 상기 유기 전계 발광 재료는 정공 주입 재료, 정공 전달 재료, 정공 보조 재료, 발광 보조 재료, 전자 차단 재료, 발광 재료(호스트 재료 및 도판트 재료 포함), 전자 버퍼 재료, 정공 차단 재료, 전자 전달 재료, 전자 주입 재료 등일 수 있다.As used herein, “organic electroluminescent material” means a material that can be used in an organic electroluminescent device, and may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may include a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, It may be an electron transporting material, an electron injecting material, or the like.
본원에서 "복수 종의 유기 전계 발광 재료"는 유기 전계 발광 소자를 구성하는 임의의 층에 포함될 수 있는 2종 이상의 화합물이 조합된 유기 전계 발광 재료를 의미하고, 유기 전계 발광 소자에 포함되기 전 (예를 들면, 증착 전) 및 포함된 후 (예를 들면, 증착 후)의 재료를 모두 의미할 수 있다. 예를 들면, 복수 종의 유기 전계 발광 재료는 정공주입층, 정공전달층, 정공보조층, 발광보조층, 전자차단층, 발광층, 전자버퍼층, 정공차단층, 전자전달층 및 전자주입층 중 하나 이상의 층에 포함될 수 있는 화합물이 2종 이상 조합된 것일 수 있다. 이러한 2종 이상의 화합물들은 같은 층 또는 다른 층에 포함될 수 있고, 혼합증착 또는 공증착되거나, 개별적으로 증착될 수 있다.As used herein, the term "plural kinds of organic electroluminescent materials" means an organic electroluminescent material in which two or more types of compounds that can be included in any layer constituting an organic electroluminescent device are combined, before being included in the organic electroluminescent device ( For example, it may refer to both a material before deposition) and after being included (eg, after deposition). For example, the plurality of organic electroluminescent materials may include one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Two or more compounds that may be included in the above layers may be combined. These two or more types of compounds may be included in the same layer or different layers, mixed vapor deposition or co-deposition, or may be deposited separately.
본원에서 "복수 종의 호스트 재료"는 2종 이상의 호스트 재료가 조합된 유기 전계 발광 재료를 의미하고, 유기 전계 발광 소자에 포함되기 전 (예를 들면, 증착 전) 및 포함된 후 (예를 들면, 증착 후)의 재료를 모두 의미할 수 있다. 본원의 복수 종의 호스트 재료는 유기 전계 발광 소자를 구성하는 임의의 발광층에 포함될 수 있는데, 상기 복수 종의 호스트 재료에 포함된 2종 이상의 화합물은 하나의 발광층에 함께 포함될 수도 있고, 각각 다른 발광층에 포함될 수도 있다. 2종 이상의 호스트 재료가 하나의 층에 포함되는 경우, 예를 들어, 혼합증착되어 층을 형성할 수도 있고, 별도로 동시에 공증착되어 층을 형성할 수도 있다.As used herein, "a plurality of types of host materials" means an organic electroluminescent material in which two or more types of host materials are combined, and before (eg, before deposition) and after being included in an organic electroluminescent device (eg, for example) , after deposition) may mean all of the materials. The plurality of types of host materials of the present application may be included in any light emitting layer constituting the organic electroluminescent device, and two or more kinds of compounds included in the plurality of types of host materials may be included in one light emitting layer, respectively, in different light emitting layers. may be included. When two or more types of host materials are included in one layer, for example, the layer may be mixed and vapor-deposited, or the layer may be separately and simultaneously co-deposited to form the layer.
본원에서 "(C1-C30)알킬"은 쇄를 구성하는 탄소수가 1 내지 30개인 직쇄 또는 분지쇄 알킬을 의미하고, 여기에서 탄소수는 바람직하게는 1 내지 20개, 더 바람직하게는 1 내지 10개이다. 상기 알킬의 구체적인 예로서, 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, tert-부틸 및 sec-부틸 등이 있다. 본원에서 "(C2-C30)알케닐"은 쇄를 구성하는 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알케닐을 의미하고, 여기에서 탄소수는 바람직하게는 2 내지 20개, 더 바람직하게는 2 내지 10개이다. 상기 알케닐의 구체적인 예로서, 비닐, 1-프로페닐, 2-프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 2-메틸부트-2-에닐 등이 있다. 본원에서 "(C2-C30)알키닐"은 쇄를 구성하는 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알키닐을 의미하고, 여기에서 탄소수는 바람직하게는 2 내지 20개, 더 바람직하게는 2 내지 10개이다. 상기 알키닐의 예로서, 에티닐, 1-프로피닐, 2-프로피닐, 1-부티닐, 2-부티닐, 3-부티닐, 1-메틸펜트-2-이닐 등이 있다. 본원에서 "(C3-C30)시클로알킬"은 환 골격 탄소수가 3 내지 30개인 단일환 또는 다환 탄화수소를 의미하고, 상기 탄소수는 바람직하게는 3 내지 20개, 더 바람직하게는 3 내지 7개이다. 상기 시클로알킬의 예로서, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로펜틸메틸, 시클로헥틸메틸 등이 있다. 본원에서 "(3-7원)헤테로시클로알킬"은 환 골격 원자수가 3 내지 7개, 바람직하게는 5 내지 7개이고, B, N, O, S, Si 및 P로 이루어진 군, 바람직하게는 O, S 및 N로 이루어진 군에서 선택되는 하나 이상의 헤테로원자를 포함하는 시클로알킬을 의미하고, 예를 들어, 테트라하이드로푸란, 피롤리딘, 티올란, 테트라하이드로피란 등이 있다. 본원에서 "(C6-C30)아릴(렌)"은 환 골격 탄소수가 6 내지 30개인 방향족 탄화수소에서 유래된 단일환 또는 융합환계 라디칼을 의미하고, 부분적으로 포화될 수도 있다. 상기 환 골격 탄소수는 바람직하게는 6 내지 25개, 더 바람직하게는 6 내지 18개이다. 상기 아릴은 스피로 구조를 가진 것을 포함한다. 상기 아릴의 예로서, 페닐, 비페닐, 터페닐, 나프틸, 비나프틸, 페닐나프틸, 나프틸페닐, 페닐터페닐, 플루오레닐, 페닐플루오레닐, 디페닐플루오레닐, 벤조플루오레닐, 디벤조플루오레닐, 페난트레닐, 페닐페난트레닐, 안트라세닐, 인데닐, 트리페닐레닐, 피레닐, 테트라세닐, 페릴레닐, 크라이세닐, 나프타세닐, 플루오란테닐, 스피로비플루오레닐, 아쥴레닐, 테트라메틸디히드로페난트레닐 등이 있다. 더욱 구체적으로, 상기 아릴의 예로는 페닐, 1-나프틸, 2-나프틸, 1-안트릴, 2-안트릴, 9-안트릴, 벤즈안트릴, 1-페난트릴, 2-페난트릴, 3-페난트릴, 4-페난트릴, 9-페난트릴, 나프타세닐, 피레닐, 1-크리세닐, 2-크리세닐, 3-크리세닐, 4-크리세닐, 5-크리세닐, 6-크리세닐, 벤조[c]페난트릴, 벤조[g]크리세닐, 1-트리페닐레닐, 2-트리페닐레닐, 3-트리페닐레닐, 4-트리페닐레닐, 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐, 9-플루오레닐, 벤조[a]플루오레닐, 벤조[b]플루오레닐, 벤조[c]플루오레닐, 디벤조플루오레닐, 2-비페닐일, 3-비페닐일, 4-비페닐일, o-터페닐, m-터페닐-4-일, m-터페닐-3-일, m-터페닐-2-일, p-터페닐-4-일, p-터페닐-3-일, p-터페닐-2-일, m-쿼터페닐, 3-플루오란테닐, 4-플루오란테닐, 8-플루오란테닐, 9-플루오란테닐, 벤조플루오란테닐, o-톨릴, m-톨릴, p-톨릴, 2,3-자일릴, 3,4-자일릴, 2,5-자일릴, 메시틸, o-쿠멘일, m-쿠멘일, p-쿠멘일, p-tert-부틸페닐, p-(2-페닐프로필)페닐, 4'-메틸비페닐일, 4"-tert-부틸-p-터페닐-4-일, 9,9-디메틸-1-플루오레닐, 9,9-디메틸-2-플루오레닐, 9,9-디메틸-3-플루오레닐, 9,9-디메틸-4-플루오레닐, 9,9-디페닐-1-플루오레닐, 9,9-디페닐-2-플루오레닐, 9,9-디페닐-3-플루오레닐, 9,9-디페닐-4-플루오레닐, 11,11-디메틸-1-벤조[a] 플루오레닐, 11,11-디메틸-2-벤조[a] 플루오레닐, 11,11-디메틸-3-벤조[a] 플루오레닐, 11,11-디메틸-4-벤조[a] 플루오레닐, 11,11-디메틸-5-벤조[a] 플루오레닐, 11,11-디메틸-6-벤조[a] 플루오레닐, 11,11-디메틸-7-벤조[a] 플루오레닐, 11,11-디메틸-8-벤조[a] 플루오레닐, 11,11-디메틸-9-벤조[a] 플루오레닐, 11,11-디메틸-10-벤조[a] 플루오레닐, 11,11-디메틸-1-벤조[b] 플루오레닐, 11,11-디메틸-2-벤조[b] 플루오레닐, 11,11-디메틸-3-벤조[b] 플루오레닐, 11,11-디메틸-4-벤조[b] 플루오레닐, 11,11-디메틸-5-벤조[b] 플루오레닐, 11,11-디메틸-6-벤조[b] 플루오레닐, 11,11-디메틸-7-벤조[b] 플루오레닐, 11,11-디메틸-8-벤조[b] 플루오레닐, 11,11-디메틸-9-벤조[b] 플루오레닐, 11,11-디메틸-10-벤조[b] 플루오레닐, 11,11-디메틸-1-벤조[c] 플루오레닐, 11,11-디메틸-2-벤조[c] 플루오레닐, 11,11-디메틸-3-벤조[c] 플루오레닐, 11,11-디메틸-4-벤조[c] 플루오레닐, 11,11-디메틸-5-벤조[c] 플루오레닐, 11,11-디메틸-6-벤조[c] 플루오레닐, 11,11-디메틸-7-벤조[c] 플루오레닐, 11,11-디메틸-8-벤조[c] 플루오레닐, 11,11-디메틸-9-벤조[c] 플루오레닐, 11,11-디메틸-10-벤조[c] 플루오레닐, 11,11-디페닐-1-벤조[a] 플루오레닐, 11,11-디페닐-2-벤조[a] 플루오레닐, 11,11-디페닐-3-벤조[a] 플루오레닐, 11,11-디페닐-4-벤조[a] 플루오레닐, 11,11-디페닐-5-벤조[a] 플루오레닐, 11,11-디페닐-6-벤조[a] 플루오레닐, 11,11-디페닐-7-벤조[a] 플루오레닐, 11,11-디페닐-8-벤조[a] 플루오레닐, 11,11-디페닐-9-벤조[a] 플루오레닐, 11,11-디페닐-10-벤조[a] 플루오레닐, 11,11-디페닐-1-벤조[b] 플루오레닐, 11,11-디페닐-2-벤조[b] 플루오레닐, 11,11-디페닐-3-벤조[b] 플루오레닐, 11,11-디페닐-4-벤조[b] 플루오레닐, 11,11-디페닐-5-벤조[b] 플루오레닐, 11,11-디페닐-6-벤조[b] 플루오레닐, 11,11-디페닐-7-벤조[b] 플루오레닐, 11,11-디페닐-8-벤조[b] 플루오레닐, 11,11-디페닐-9-벤조[b] 플루오레닐, 11,11-디페닐-10-벤조[b] 플루오레닐, 11,11-디페닐-1-벤조[c] 플루오레닐, 11,11-디페닐-2-벤조[c] 플루오레닐, 11,11-디페닐-3-벤조[c] 플루오레닐, 11,11-디페닐-4-벤조[c] 플루오레닐, 11,11-디페닐-5-벤조[c] 플루오레닐, 11,11-디페닐-6-벤조[c] 플루오레닐, 11,11-디페닐-7-벤조[c] 플루오레닐, 11,11-디페닐-8-벤조[c] 플루오레닐, 11,11-디페닐-9-벤조[c] 플루오레닐, 11,11-디페닐-10-벤조[c]플루오레닐, 9,9,10,10-테트라메틸-9,10-디히드로-1-페난트레닐, 9,9,10,10-테트라메틸-9,10-디히드로-2-페난트레닐, 9,9,10,10-테트라메틸-9,10-디히드로-3-페난트레닐, 9,9,10,10-테트라메틸-9,10-디히드로-4-페난트레닐 등을 들 수 있다.As used herein, "(C1-C30)alkyl" means a straight-chain or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl and sec-butyl. As used herein, "(C2-C30) alkenyl" means a straight or branched chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20, more preferably 2 to It is 10. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbut-2-enyl. As used herein, "(C2-C30) alkynyl" means a straight or branched chain alkynyl having 2 to 30 carbon atoms constituting the chain, wherein the carbon number is preferably 2 to 20, more preferably 2 to It is 10. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. As used herein, "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7, preferably 5 to 7, ring skeleton atoms, and the group consisting of B, N, O, S, Si and P, preferably O , S and means a cycloalkyl containing one or more heteroatoms selected from the group consisting of N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. As used herein, “(C6-C30)aryl(ene)” refers to a monocyclic or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, and may be partially saturated. The number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzoflu Orenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobi fluorenyl, azulenyl, tetramethyldihydrophenanthrenyl, and the like. More specifically, examples of the aryl include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-Phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl , benzo [c] phenanthryl, benzo [g] chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl , 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [a] fluorenyl, benzo [b] fluorenyl, benzo [c] fluorenyl, dibenzo fluorenyl, 2 -biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p -terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9 -Fluorantenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl , m-cumenyl, p-cumenyl, p- tert -butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4" -tert -butyl-p-terphenyl-4- yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorene nyl, 11,11-dimethyl-1-benzo [a] fluorenyl, 11,11-dimethyl-2-benzo [a] fluorenyl, 11,11-dimethyl-3-benzo [a] fluorenyl, 11,11-dimethyl-4-benzo [a] fluorenyl, 11,11-dimethyl-5-benzo [a] fluorenyl, 11,11-dimethyl-6-benzo [a] fluorenyl, 11, 11-dimethyl-7-benzo [a] fluorenyl, 11,11-dimethyl-8-benzo [a] fluorenyl, 11,11-dimethyl-9-benzo [a] fluorenyl, 11,11- Dimethyl-10-benzo [a] fluorenyl, 11 ,11-dimethyl-1-benzo [b] fluorenyl, 11,11-dimethyl-2-benzo [b] fluorenyl, 11,11-dimethyl-3-benzo [b] fluorenyl, 11,11 -dimethyl-4-benzo [b] fluorenyl, 11,11-dimethyl-5-benzo [b] fluorenyl, 11,11-dimethyl-6-benzo [b] fluorenyl, 11,11-dimethyl -7-benzo [b] fluorenyl, 11,11-dimethyl-8-benzo [b] fluorenyl, 11,11-dimethyl-9-benzo [b] fluorenyl, 11,11-dimethyl-10 -benzo [b] fluorenyl, 11,11-dimethyl-1-benzo [c] fluorenyl, 11,11-dimethyl-2-benzo [c] fluorenyl, 11,11-dimethyl-3-benzo [c] fluorenyl, 11,11-dimethyl-4-benzo [c] fluorenyl, 11,11-dimethyl-5-benzo [c] fluorenyl, 11,11-dimethyl-6-benzo [c] ] Fluorenyl, 11,11-dimethyl-7-benzo [c] fluorenyl, 11,11-dimethyl-8-benzo [c] fluorenyl, 11,11-dimethyl-9-benzo [c] flu Orenyl, 11,11-dimethyl-10-benzo [c] fluorenyl, 11,11-diphenyl-1-benzo [a] fluorenyl, 11,11-diphenyl-2-benzo [a] flu Orenyl, 11,11-diphenyl-3-benzo [a] fluorenyl, 11,11-diphenyl-4-benzo [a] fluorenyl, 11,11-diphenyl-5-benzo [a] Fluorenyl, 11,11-diphenyl-6-benzo [a] fluorenyl, 11,11-diphenyl-7-benzo [a] fluorenyl, 11,11-diphenyl-8-benzo [a] ] fluorenyl, 11,11-diphenyl-9-benzo [a] fluorenyl, 11,11-diphenyl-10-benzo [a] fluorenyl, 11,11-diphenyl-1-benzo [ b] fluorenyl, 11,11-diphenyl-2-benzo [b] fluorenyl, 11,11-diphenyl-3-benzo [b] fluorenyl, 11,11-diphenyl-4-benzo [b] fluorenyl, 11,11-diphenyl-5-benzo [b] fluorenyl, 11,11-diphenyl-6-benzo [b] fluorenyl, 11,11-diphenyl-7- Benzo [b] fluorenyl, 11,11-diphenyl-8-benzo [b] fluorenyl, 11,11-diphenyl-9-benzo [b] fluorenyl, 11,11-diphenyl-10 -benzo[b] fluorenyl , 11,11-diphenyl-1-benzo [c] fluorenyl, 11,11-diphenyl-2-benzo [c] fluorenyl, 11,11-diphenyl-3-benzo [c] fluorene nyl, 11,11-diphenyl-4-benzo [c] fluorenyl, 11,11-diphenyl-5-benzo [c] fluorenyl, 11,11-diphenyl-6-benzo [c] flu Orenyl, 11,11-diphenyl-7-benzo [c] fluorenyl, 11,11-diphenyl-8-benzo [c] fluorenyl, 11,11-diphenyl-9-benzo [c] Fluorenyl, 11,11-diphenyl-10-benzo [c] fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10 ,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10 -tetramethyl-9,10-dihydro-4-phenanthrenyl, etc. are mentioned.
본원에서 "(3-30원)헤테로아릴(렌)"은 환 골격 원자수가 3 내지 30개이고, B, N, O, S, Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자를 포함하는 아릴기 또는 아릴렌기를 의미한다. 헤테로원자수는 바람직하게는 1 내지 4개이고, 단일 환계이거나 하나 이상의 벤젠환과 축합된 융합환계일 수 있으며, 부분적으로 포화될 수도 있다. 또한, 본원에서 상기 헤테로아릴 또는 헤테로아릴렌은 하나 이상의 헤테로아릴 또는 아릴기가 단일결합에 의해 헤테로아릴기와 연결된 형태도 포함하며, 스피로 구조를 가진 것도 포함한다. 상기 헤테로아릴의 예로서, 푸릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 푸라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단일 환계 헤테로아릴, 벤조푸라닐, 벤조티오페닐, 이소벤조푸라닐, 디벤조푸라닐, 디벤조티오페닐, 디벤조셀레노페닐, 나프토벤조푸라닐, 나프토벤조티오페닐, 벤조푸로퀴놀리닐, 벤조푸로퀴나졸리닐, 벤조푸로나프티리디닐, 벤조푸로피리미디닐, 나프토푸로피리미디닐, 벤조티에노퀴놀리닐, 벤조티에노퀴나졸리닐, 벤조티에노나프티리디닐, 벤조티에노피리미디닐, 나프토티에노피리미디닐, 피리미도인돌릴, 벤조피리미도인돌릴, 벤조푸로피라지닐, 나프토푸로피라지닐, 벤조티에노피라지닐, 나프토티에노피라지닐, 피라지노인돌릴, 벤조피라지노인돌릴, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 벤조인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 벤조퀴나졸리닐, 퀴녹살리닐, 벤조퀴녹살리닐, 나프티리디닐, 카바졸릴, 벤조카바졸릴, 디벤조카바졸릴, 페녹사진일, 페노티아진일, 페난트리딘일, 벤조디옥솔릴, 디하이드로아크리디닐, 벤조트리아졸페나진, 이미다조피리딘, 크로메노퀴나졸리닐, 티오크로메노퀴나졸리닐, 디메틸벤조페리미디닐, 인돌로카바졸릴, 인데노카바졸릴 등의 융합 환계 헤테로아릴 등이 있다. 더욱 구체적으로, 상기 헤테로아릴의 예로는, 1-피롤릴, 2-피롤릴, 3-피롤릴, 피라지닐, 2-피리디닐, 2-피리미디닐, 4-피리미디닐, 5-피리미디닐, 6-피리미디닐, 1,2,3-트리아진-4-일, 1,2,4-트리아진-3-일, 1,3,5-트리아진-2-일, 1-이미다졸릴, 2-이미다졸릴, 1-피라졸릴, 1-인돌리디닐, 2-인돌리디닐, 3-인돌리디닐, 5-인돌리디닐, 6-인돌리디닐, 7-인돌리디닐, 8-인돌리디닐, 2-이미다조피리디닐, 3-이미다조피리디닐, 5-이미다조피리디닐, 6-이미다조피리디닐, 7-이미다조피리디닐, 8-이미다조피리디닐, 3-피리디닐, 4-피리디닐, 1-인돌릴, 2-인돌릴, 3-인돌릴, 4-인돌릴, 5-인돌릴, 6-인돌릴, 7-인돌릴, 1-이소인돌릴, 2-이소인돌릴, 3-이소인돌릴, 4-이소인돌릴, 5-이소인돌릴, 6-이소인돌릴, 7-이소인돌릴, 2-푸릴, 3-푸릴, 2-벤조푸라닐, 3-벤조푸라닐, 4-벤조푸라닐, 5-벤조푸라닐, 6-벤조푸라닐, 7-벤조푸라닐, 1-이소벤조푸라닐, 3-이소벤조푸라닐, 4-이소벤조푸라닐, 5-이소벤조푸라닐, 6-이소벤조푸라닐, 7-이소벤조푸라닐, 2-퀴놀릴, 3-퀴놀릴, 4-퀴놀릴, 5-퀴놀릴, 6-퀴놀릴, 7-퀴놀릴, 8-퀴놀릴, 1-이소퀴놀릴, 3-이소퀴놀릴, 4-이소퀴놀릴, 5-이소퀴놀릴, 6-이소퀴놀릴, 7-이소퀴놀릴, 8-이소퀴놀릴, 2-퀴녹살리닐, 5-퀴녹살리닐, 6-퀴녹살리닐, 1-카르바졸릴, 2-카르바졸릴, 3-카르바졸릴, 4-카르바졸릴, 9-카르바졸릴, 아자카르바졸릴-1-일, 아자카르바졸릴-2-일, 아자카르바졸릴-3-일, 아자카르바졸릴-4-일, 아자카르바졸릴-5-일, 아자카르바졸릴-6-일, 아자카르바졸릴-7-일, 아자카르바졸릴-8-일, 아자카르바졸릴-9-일, 1-페난트리디닐, 2-페난트리디닐, 3-페난트리디닐, 4-페난트리디닐, 6-페난트리디닐, 7-페난트리디닐, 8-페난트리디닐, 9-페난트리디닐, 10-페난트리디닐, 1-아크리디닐, 2-아크리디닐, 3-아크리디닐, 4-아크리디닐, 9-아크리디닐, 2-옥사졸릴, 4-옥사졸릴, 5-옥사졸릴, 2-옥사디아졸릴, 5-옥사디아졸릴, 3-푸라자닐, 2-티에닐, 3-티에닐, 2-메틸피롤-1-일, 2-메틸피롤-3-일, 2-메틸피롤-4-일, 2-메틸피롤-5-일, 3-메틸피롤-1-일, 3-메틸피롤-2-일, 3-메틸피롤-4-일, 3-메틸피롤-5-일, 2-tert-부틸피롤-4-일, 3-(2-페닐프로필)피롤-1-일, 2-메틸-1-인돌릴, 4-메틸-1-인돌릴, 2-메틸-3-인돌릴, 4-메틸-3-인돌릴, 2-tert-부틸-1-인돌릴, 4-tert-부틸-1-인돌릴, 2-tert-부틸-3-인돌릴, 4-tert-부틸-3-인돌릴, 1-디벤조푸라닐, 2-디벤조푸라닐, 3-디벤조푸라닐, 4-디벤조푸라닐, 1-디벤조티오페닐, 2-디벤조티오페닐, 3-디벤조티오페닐, 4-디벤조티오페닐, 1-나프토-[1,2-b]-벤조푸라닐, 2-나프토-[1,2-b]-벤조푸라닐, 3-나프토-[1,2-b]-벤조푸라닐, 4-나프토-[1,2-b]-벤조푸라닐, 5-나프토-[1,2-b]-벤조푸라닐, 6-나프토-[1,2-b]-벤조푸라닐, 7-나프토-[1,2-b]-벤조푸라닐, 8-나프토-[1,2-b]-벤조푸라닐, 9-나프토-[1,2-b]-벤조푸라닐, 10-나프토-[1,2-b]-벤조푸라닐, 1-나프토-[2,3-b]-벤조푸라닐, 2-나프토-[2,3-b]-벤조푸라닐, 3-나프토-[2,3-b]-벤조푸라닐, 4-나프토-[2,3-b]-벤조푸라닐, 5-나프토-[2,3-b]-벤조푸라닐, 6-나프토-[2,3-b]-벤조푸라닐, 7-나프토-[2,3-b]-벤조푸라닐, 8-나프토-[2,3-b]-벤조푸라닐, 9-나프토-[2,3-b]-벤조푸라닐, 10-나프토-[2,3-b]-벤조푸라닐, 1-나프토-[2,1-b]-벤조푸라닐, 2-나프토-[2,1-b]-벤조푸라닐, 3-나프토-[2,1-b]-벤조푸라닐, 4-나프토-[2,1-b]-벤조푸라닐, 5-나프토-[2,1-b]-벤조푸라닐, 6-나프토-[2,1-b]-벤조푸라닐, 7-나프토-[2,1-b]-벤조푸라닐, 8-나프토-[2,1-b]-벤조푸라닐, 9-나프토-[2,1-b]-벤조푸라닐, 10-나프토-[2,1-b]-벤조푸라닐, 1-나프토-[1,2-b]-벤조티오페닐, 2-나프토-[1,2-b]-벤조티오페닐, 3-나프토-[1,2-b]-벤조티오페닐, 4-나프토-[1,2-b]-벤조티오페닐, 5-나프토-[1,2-b]-벤조티오페닐, 6-나프토-[1,2-b]-벤조티오페닐, 7-나프토-[1,2-b]-벤조티오페닐, 8-나프토-[1,2-b]-벤조티오페닐, 9-나프토-[1,2-b]-벤조티오페닐, 10-나프토-[1,2-b]-벤조티오페닐, 1-나프토-[2,3-b]-벤조티오페닐, 2-나프토-[2,3-b]-벤조티오페닐, 3-나프토-[2,3-b]-벤조티오페닐, 4-나프토-[2,3-b]-벤조티오페닐, 5-나프토-[2,3-b]-벤조티오페닐, 1-나프토-[2,1-b]-벤조티오페닐, 2-나프토-[2,1-b]-벤조티오페닐, 3-나프토-[2,1-b]-벤조티오페닐, 4-나프토-[2,1-b]-벤조티오페닐, 5-나프토-[2,1-b]-벤조티오페닐, 6-나프토-[2,1-b]-벤조티오페닐, 7-나프토-[2,1-b]-벤조티오페닐, 8-나프토-[2,1-b]-벤조티오페닐, 9-나프토-[2,1-b]-벤조티오페닐, 10-나프토-[2,1-b]-벤조티오페닐, 2-벤조푸로[3,2-d]피리미디닐, 6-벤조푸로[3,2-d]피리미디닐, 7-벤조푸로[3,2-d]피리미디닐, 8-벤조푸로[3,2-d]피리미디닐, 9-벤조푸로[3,2-d]피리미디닐, 2-벤조티오[3,2-d]피리미디닐, 6-벤조티오[3,2-d]피리미디닐, 7-벤조티오[3,2-d]피리미디닐, 8-벤조티오[3,2-d]피리미디닐, 9-벤조티오[3,2-d]피리미디닐, 2-벤조푸로[3,2-d]피라지닐, 6-벤조푸로[3,2-d]피라지닐, 7-벤조푸로[3,2-d]피리지닐, 8-벤조푸로[3,2-d]피라지닐, 9-벤조푸로[3,2-d]피라지닐, 2-벤조티오[3,2-d]피라지닐, 6-벤조티오[3,2-d]피라지닐, 7-벤조티오[3,2-d]피라지닐, 8-벤조티오[3,2-d]피라지닐, 9-벤조티오[3,2-d]피라지닐, 1-실라플루오레닐, 2-실라플루오레닐, 3-실라플루오레닐, 4-실라플루오레닐, 1-게르마플루오레닐, 2-게르마플루오레닐, 3-게르마플루오레닐, 4-게르마플루오레닐, 1-디벤조셀레노페닐, 2-디벤조셀레노페닐, 3-디벤조셀레노페닐, 4-디벤조셀레노페닐 등을 들 수 있다. 본원에서 "할로겐"은 F, Cl, Br 및 I 원자를 포함한다.As used herein, "(3-30 membered) heteroaryl (ene)" is an aryl group having 3 to 30 ring skeleton atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P or an arylene group. The number of hetero atoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl or heteroarylene herein includes a form in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and includes those having a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, monocyclic heteroaryl such as pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzo Thiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidi Nyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuro Pyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl , benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinox Salinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolephenazine, imidazo and fused ring heteroaryls such as pyridine, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperiimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi nyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imi Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imida Zopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1 -isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2 -benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4 -Isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-qui Nolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8- Isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carba Zolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarba Zolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl , 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3 -acridinyl, 4-acridinyl, 9-acridinyl , 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1- Yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methyl Pyrrol-4-yl, 3-methylpyrrol-5-yl, 2- tert -butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4 -Methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -Butyl-3-indolyl, 4- tert -Butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1- Dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1 ,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[ 1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho- [1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho -[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naph To-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7- Naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10 -naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl , 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofura Neil, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl , 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho- [1,2-b]-benzothio Phenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzo Thiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]- Benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b] -benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho- [2,1-b ]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho- [2,1- b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1 -b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2, 1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d] Pyrimidinyl, 8-benzofuro [3,2-d] pyrimidinyl, 9-benzofuro [3,2-d] pyrimidinyl, 2-benzothio [3,2-d] pyrimidinyl, 6 -benzothio [3,2-d] pyrimidinyl, 7-benzothio [3,2-d] pyrimidinyl, 8-benzothio [3,2-d] pyrimidinyl, 9-benzothio [3 ,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl , 8-benzofuro [3,2-d] pyrazinyl, 9-benzofuro [3,2-d] pyrazinyl, 2-benzothio [3,2-d] pyrazinyl, 6-benzothio [3, 2-d] pyrazinyl, 7-benzothio [3,2-d] pyrazinyl, 8-benzothio [3,2-d] pyrazinyl, 9-benzothio [3,2-d] pyrazinyl, 1 -silafluorenyl, 2-sila Fluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. are mentioned. As used herein, “halogen” includes F, Cl, Br and I atoms.
또한, "오르토(ortho; o-)", "메타(meta; m-)", 및 "파라(para; p-)"는 각각 치환기의 상대적인 위치를 나타내는 접두어이다. 오르토(ortho)는 2개의 치환기가 서로 이웃하는 것을 나타내고, 일 예로 벤젠 치환체에서 치환기가 1, 2 위치에 있을 때, 오르토 위치라고 한다. 메타(meta)는 2개의 치환기가 1, 3 위치에 있는 것을 나타내며, 일 예로 벤젠 치환체에서 치환기가 1, 3 위치에 있을 때 메타 위치라고 한다. 파라(para)는 2개의 치환기가 1, 4 위치에 있는 것을 나타내며, 일 예로 벤젠 치환체에서 치환기가 1, 4 위치에 있을 때 파라 위치라고 한다.Also, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes indicating the relative position of a substituent, respectively. Ortho (ortho) indicates that two substituents are adjacent to each other, and for example, when the substituents are at positions 1 and 2 in a benzene substituent, it is referred to as an ortho position. Meta indicates that two substituents are at positions 1 and 3, for example, when a substituent is at positions 1 and 3 in a benzene substituent, it is referred to as a meta position. Para (para) indicates that two substituents are at positions 1 and 4, for example, when the substituents are at positions 1 and 4 in a benzene substituent, it is referred to as a para position.
또한, 본원에 기재되어 있는 "치환 또는 비치환"이라는 기재에서 "치환"은 어떤 작용기에서 수소 원자가 다른 원자 또는 다른 작용기 (즉, 치환기)로 대체되는 것을 뜻하고, 상기 치환기 중 2 이상의 치환기가 연결된 기로 치환되는 것도 포함한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 피리딘-트리아진일 수 있다. 즉, 피리딘-트리아진은 하나의 헤테로아릴 치환기로 해석될 수도 있고, 2개의 헤테로아릴 치환기가 연결된 치환기로 해석될 수도 있다. 본원 화학식들에서의 치환된 알킬, 치환된 알케닐, 치환된 아릴, 치환된 아릴렌, 치환된 헤테로아릴, 치환된 헤테로아릴렌, 치환된 질소 함유 헤테로아릴, 치환된 시클로알킬, 치환된 알콕시, 치환된 트리알킬실릴, 치환된 디알킬아릴실릴, 치환된 알킬디아릴실릴, 치환된 트리아릴실릴, 및 치환된 지방족고리와 방향족고리의 융합고리기의 치환기는 각각 독립적으로 중수소; 할로겐; 시아노; 카르복실; 니트로; 히드록시; 포스핀옥사이드; (C1-C30)알킬; 할로(C1-C30)알킬; (C2-C30)알케닐; (C2-C30)알키닐; (C1-C30)알콕시; (C1-C30)알킬티오; (C3-C30)시클로알킬; (C3-C30)시클로알케닐; (3-7원)헤테로시클로알킬; (C6-C30)아릴옥시; (C6-C30)아릴티오; (C1-C30)알킬 및 (C6-C30)아릴 중 하나 이상으로 치환 또는 비치환된 (3-30 원)헤테로아릴; 중수소, 시아노, (C1-C30)알킬, (C3-C30)시클로알킬, 트리(C1-C30)알킬실릴, (C6-C30)아릴 및 (3-30원)헤테로아릴 중 하나 이상으로 치환 또는 비치환된 (C6-C30)아릴; 트리(C1-C30)알킬실릴; 트리(C6-C30)아릴실릴; 디(C1-C30)알킬(C6-C30)아릴실릴; (C1-C30)알킬디(C6-C30)아릴실릴; (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기; 아미노; 모노- 또는 디- (C1-C30)알킬아미노; 모노- 또는 디- (C2-C30)알케닐아미노; (C1-C30)알킬(C2-C30)알케닐아미노; 모노- 또는 디- (C6-C30)아릴아미노; (C1-C30)알킬(C6-C30)아릴아미노; 모노- 또는 디- (3-30원)헤테로아릴아미노; (C1-C30)알킬(3-30원)헤테로아릴아미노; (C2-C30)알케닐(C6-C30)아릴아미노; (C2-C30)알케닐(3-30원)헤테로아릴아미노; (C6-C30)아릴(3-30원)헤테로아릴아미노; (C1-C30)알킬카보닐; (C1-C30)알콕시카보닐; (C6-C30)아릴카보닐; (C6-C30)아릴포스핀; 디(C6-C30)아릴보로닐; 디(C1-C30)알킬보로닐; (C1-C30)알킬(C6-C30)아릴보로닐; (C6-C30)아르(C1-C30)알킬; 및 (C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 하나 이상이다. 본원의 일양태에 따르면, 상기 치환기는 각각 독립적으로 중수소; 시아노; (C1-C20)알킬; (C6-C25)시클로알킬; 하나 이상의 (C6-C25)아릴로 치환 또는 비치환된 (5-25원)헤테로아릴; 중수소, 시아노, (C1-C20)알킬, (C6-C25)시클로알킬, 트리(C1-C20)알킬실릴, (C6-C25)아릴 및 (5-25원)헤테로아릴 중 하나 이상으로 치환 또는 비치환된 (C6-C25)아릴; 모노- 또는 디- (C6-C25)아릴아미노; 모노- 또는 디- (5-25원)헤테로아릴아미노; 및 (C6-C25)아릴(5-25원)헤테로아릴아미노로 이루어진 군으로부터 선택되는 하나 이상이다. 본원의 다른 일 양태에 따르면, 상기 치환기는 각각 독립적으로 중수소; 시아노; (C1-C10)알킬; (C6-C18)시클로알킬; 하나 이상의 (C6-C18)아릴로 치환 또는 비치환된 (5-20원)헤테로아릴; 중수소, 시아노, (C1-C10)알킬, (C6-C18)시클로알킬, 트리(C1-C10)알킬실릴, (C6-C15)아릴 및 (5-20원)헤테로아릴 중 하나 이상으로 치환 또는 비치환된 (C6-C25)아릴; 디(C6-C18)아릴아미노; 및 (C6-C18)아릴(5-20원)헤테로아릴아미노로 이루어진 군으로부터 선택되는 하나 이상이다. 구체적으로, 상기 치환기는 각각 독립적으로 중수소; 시아노; 메틸; 시클로헥실; 치환 또는 비치환된 페닐; 나프틸; 페닐나프틸; 비페닐; 메틸플루오레닐; 디메틸플루오레닐; 디페닐플루오레닐; 페난트레닐; 안트라세닐; 플루오란테닐; 터페닐; 크라이세닐; 트리페닐레닐; 스피로비플루오레닐; 페닐로 치환된 피리딜; 페닐로 치환된 벤조이미다졸릴; 페닐 및 나프틸로 이루어진 그룹으로부터 선택된 하나 이상으로 치환된 트리아진일; 벤조티오페닐; 디벤조티오페닐; 페닐 및/또는 비페닐로 치환 또는 비치환된 디벤조푸라닐; 페닐로 치환 또는 비치환된 카바졸릴; 페닐로 치환된 나프토옥사졸릴; 디페닐아미노; 디비페닐아미노; 페닐비페닐아미노; 페닐디벤조티오푸란일아미노; 및 페닐디벤조티오페닐아미노 등일 수 있고, 상기 치환된 페닐의 치환기는 중수소, 시아노, 메틸, tert-부틸, 나프틸, 트리메틸실릴, 카바졸릴 및 시클로헥실 중 하나 이상일 수 있다.In addition, in the description of "substituted or unsubstituted" as used herein, "substitution" means that a hydrogen atom in one functional group is replaced by another atom or another functional group (ie, a substituent), and two or more substituents among the substituents are connected It includes those substituted with a group. For example, "a substituent to which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be interpreted as a single heteroaryl substituent or as a substituent in which two heteroaryl substituents are connected. substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted nitrogen containing heteroaryl, substituted cycloalkyl, substituted alkoxy, Substituents of substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted aliphatic and aromatic ring fused ring groups are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered) heteroaryl unsubstituted or substituted with one or more of (C1-C30)alkyl and (C6-C30)aryl; substituted with one or more of deuterium, cyano, (C1-C30)alkyl, (C3-C30)cycloalkyl, tri(C1-C30)alkylsilyl, (C6-C30)aryl and (3-30 membered)heteroaryl; unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; a fused ring group of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30); amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; (C1-C30)alkyl(C2-C30)alkenylamino; mono- or di- (C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30) alkenyl (3-30 membered) heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30) arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one aspect of the present application, the substituents are each independently deuterium; cyano; (C1-C20)alkyl; (C6-C25)cycloalkyl; (5-25 membered)heteroaryl unsubstituted or substituted with one or more (C6-C25)aryl; substituted with one or more of deuterium, cyano, (C1-C20)alkyl, (C6-C25)cycloalkyl, tri(C1-C20)alkylsilyl, (C6-C25)aryl and (5-25 membered)heteroaryl; unsubstituted (C6-C25)aryl; mono- or di- (C6-C25)arylamino; mono- or di- (5-25 membered) heteroarylamino; and (C6-C25)aryl (5-25 membered)heteroarylamino. According to another aspect of the present application, the substituents are each independently deuterium; cyano; (C1-C10)alkyl; (C6-C18)cycloalkyl; (5-20 membered)heteroaryl unsubstituted or substituted with one or more (C6-C18)aryl; substituted with one or more of deuterium, cyano, (C1-C10)alkyl, (C6-C18)cycloalkyl, tri(C1-C10)alkylsilyl, (C6-C15)aryl and (5-20 membered)heteroaryl; unsubstituted (C6-C25)aryl; di(C6-C18)arylamino; and (C6-C18)aryl (5-20 membered)heteroarylamino. Specifically, the substituents are each independently deuterium; cyano; methyl; cyclohexyl; substituted or unsubstituted phenyl; naphthyl; phenylnaphthyl; biphenyl; methylfluorenyl; dimethyl fluorenyl; diphenylfluorenyl; phenanthrenyl; anthracenyl; fluoranthenyl; terphenyl; chrysenyl; triphenylenyl; spirobifluorenyl; pyridyl substituted with phenyl; phenyl-substituted benzimidazolyl; triazinyl substituted with one or more selected from the group consisting of phenyl and naphthyl; benzothiophenyl; dibenzothiophenyl; dibenzofuranyl unsubstituted or substituted with phenyl and/or biphenyl; phenyl-substituted or unsubstituted carbazolyl; naphthooxazolyl substituted with phenyl; diphenylamino; dibiphenylamino; phenylbiphenylamino; phenyldibenzothiofuranylamino; and phenyldibenzothiophenylamino, and the like, and the substituent of the substituted phenyl may be one or more of deuterium, cyano, methyl, tert -butyl, naphthyl, trimethylsilyl, carbazolyl and cyclohexyl.
본원 화학식에서, 인접한 치환기와 연결되어 고리를 형성하는 경우, 상기 고리는 인접한 두 개 이상의 치환기가 연결되어 형성되는 치환 또는 비치환된 (3-30원) 단일환 또는 다환의 지환족, 방향족 또는 이들의 조합의 고리일 수 있다. 또한, 형성된 고리는 B, N, O, S, Si 및 P로부터 선택되는 하나 이상의 헤테로원자, 바람직하게는 N, O 및 S로부터 선택되는 하나 이상의 헤테로원자를 포함할 수 있다. 본원의 일 양태에 따르면, 상기 환 골격 원자수는 (5-20원)이고, 본원의 다른 일 양태에 따르면, 상기 환 골격 원자수는 (5-15원)이다.In the present formula, when connected to adjacent substituents to form a ring, the ring is a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic or these formed by connecting two or more adjacent substituents. It may be a ring of a combination of The ring formed may also contain one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. According to one aspect of the present application, the number of ring skeleton atoms is (5 to 20 members), and according to another aspect of the present application, the number of ring skeleton atoms is (5 to 15 members).
본원 화학식에서, 헤테로아릴, 헤테로아릴렌 및 헤테로시클로알킬은 각각 독립적으로 B, N, O, S, Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함할 수 있다. 또한, 상기 헤테로원자는 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 모노- 또는 디- (C1-C30)알킬아미노, 치환 또는 비치환된 모노- 또는 디- (C6-C30)아릴아미노, 및 치환 또는 비치환된 (C1-C30)알킬(C6-C30)아릴아미노로 이루어진 군으로부터 선택되는 하나 이상이 결합될 수 있다.In the formula herein, heteroaryl, heteroarylene and heterocycloalkyl may each independently comprise one or more heteroatoms selected from B, N, O, S, Si and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1 -C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)aryl One or more selected from the group consisting of amino may be bonded.
본원에 따르면 하기 화학식 2' 또는 화학식 2"의 유기 전계 발광 화합물을 포함하는 유기 전계 발광 소자가 제공된다. 여기서, 화학식 2' 또는 화학식 2"의 유기 전계 발광 화합물은 발광층 또는 전자 전달층에 포함될 수 있다.According to the present application, there is provided an organic electroluminescent device comprising an organic electroluminescent compound of Formula 2' or Formula 2". Here, the organic electroluminescent compound of Formula 2' or Formula 2" may be included in the emission layer or the electron transport layer. have.
상기 화학식 2'로 표시되는 화합물에 대해 보다 구체적으로 설명하면 다음과 같다.The compound represented by Formula 2' will be described in more detail as follows.
[화학식 2'][Formula 2']
상기 화학식 2'에서,In Formula 2',
HAr은 각각 독립적으로 치환 또는 비치환된 트리아지닐, 치환 또는 비치환된 피리딜, 치환 또는 비치환된 피리미디닐, 치환 또는 비치환된 퀴나졸리닐, 치환 또는 비치환된 벤조퀴나졸리닐, 치환 또는 비치환된 퀴녹살리닐, 치환 또는 비치환된 벤조퀴녹살리닐, 치환 또는 비치환된 벤조푸로피리미디닐, 또는 치환 또는 비치환된 벤조티에노피리미디닐이고;Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;Ar 11 is each independently any one of Formulas 3 to 5;
[화학식 3] [화학식 4] [화학식 5][Formula 3] [Formula 4] [Formula 5]
상기 화학식 3 내지 5에서,In Formulas 3 to 5,
Y2는 O 또는 S이며;Y 2 is O or S;
R20 내지 R29은 수소 또는 중수소이고;R 20 to R 29 are hydrogen or deuterium;
e는 1 또는 2이며, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있으며;e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
*는 L11와 연결되는 위치를 나타내고;* indicates a position connected to L 11 ;
단, HAr이 치환된 트리아지닐인 경우, 트리아지닐의 치환기는 각각 독립적으로 중수소, 페닐, 나프틸, 비페닐, 터페닐, 페난트레닐, 트리페닐레닐, 디메틸플루오레닐, 플루오란테닐, 크라이세닐, 카바졸릴 및 이들의 조합으로부터 선택되고, 치환기가 2개인 경우 이들은 서로 같거나 상이하다.However, when HAr is substituted triazinyl, the substituents of triazinyl are each independently deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, fluoranthenyl, cry senyl, carbazolyl, and combinations thereof, and when there are two substituents, they are the same as or different from each other.
상기 화학식 2'로 표시되는 화합물은 하기의 화합물들로부터 선택되는 하나 이상일 수 있으나, 이들에 한정되는 것은 아니다.The compound represented by Formula 2' may be one or more selected from the following compounds, but is not limited thereto.
상기 화학식 2"로 표시되는 화합물에 대해 보다 구체적으로 설명하면 다음과 같다.The compound represented by Formula 2" will be described in more detail as follows.
[화학식 2"][Formula 2"]
상기 화학식 2"에서,In Formula 2",
HAr은 각각 독립적으로 치환 또는 비치환된 트리아지닐, 치환 또는 비치환된 퀴나졸리닐, 치환 또는 비치환된 벤조퀴나졸리닐, 치환 또는 비치환된 퀴녹살리닐, 치환 또는 비치환된 벤조퀴녹살리닐, 치환 또는 비치환된 벤조푸로피리미디닐, 또는 치환 또는 비치환된 벤조티에노피리미디닐이고;Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl , a substituted or unsubstituted benzofuropyrimidinyl, or a substituted or unsubstituted benzothienopyrimidinyl;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;Ar 11 is each independently any one of Formulas 3 to 5;
[화학식 3] [화학식 4] [화학식 5][Formula 3] [Formula 4] [Formula 5]
상기 화학식 3 내지 5에서,In Formulas 3 to 5,
Y2는 O 또는 S이며;Y 2 is O or S;
R21 내지 R24 및 R26 내지 R29은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;R 21 to R 24 and R 26 to R 29 are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R20 및 R25는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이며;R 20 and R 25 are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
e는 1 또는 2이고, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있으며;e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
*는 L11와 연결되는 위치를 나타낸다.* indicates a position connected to L 11 .
상기 화학식 2"로 표시되는 화합물은 하기의 화합물들로부터 선택되는 하나 이상일 수 있으나, 이들에 한정되는 것은 아니다.The compound represented by Formula 2" may be one or more selected from the following compounds, but is not limited thereto.
본원에 일 양태에 따른 복수 종의 호스트 재료는, 상기 화학식 1로 표시되는 화합물을 포함하는 제1 호스트 재료, 및 상기 화학식 2로 표시되는 화합물을 포함하는 제2 호스트 재료를 포함하고, 본원에 일 양태에 따른 유기 전계 발광 소자의 발광층에 포함될 수 있다.A plurality of host materials according to an aspect herein include a first host material including a compound represented by Formula 1, and a second host material including a compound represented by Formula 2, and It may be included in the light emitting layer of the organic electroluminescent device according to the embodiment.
상기 화학식 1로 표시되는 화합물에 대해 보다 구체적으로 설명하면 다음과 같다.The compound represented by Formula 1 will be described in more detail as follows.
상기 화학식 1 에서, X1 및 Y1은 각각 독립적으로 -N=, -NR5-, -O- 또는 -S-이고, 단, X1 및 Y1 중 어느 하나는 -N=이고, X1 및 Y1 중 다른 하나는 -NR5-, -O- 또는 -S-이다. 본원의 일 양태에 따르면, X1 및 Y1 중 어느 하나는 -N=이고, 다른 하나는 -O- 또는 -S-이다. 즉, X1은 -N= 이고 Y1은 -O-, X1은 -N= 이고 Y1은 -S-, X1은 -O- 이고 Y1은 -N=, 또는 X1은 -S- 이고 Y1은 -N=일 수 있다. In Formula 1, X 1 and Y 1 are each independently -N=, -NR 5 -, -O- or -S-, with the proviso that any one of X 1 and Y 1 is -N=, X 1 and the other of Y 1 is -NR 5 -, -O- or -S-. According to an aspect of the present application, any one of X 1 and Y 1 is -N=, and the other is -O- or -S-. That is, X 1 is -N= and Y 1 is -O-, X 1 is -N= and Y 1 is -S-, X 1 is -O- and Y 1 is -N=, or X 1 is -S - and Y 1 may be -N=.
상기 화학식 1 에서, R1은 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이다. 본원의 일 양태에 따르면, R1은 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-25원)헤테로아릴이다. 본원의 다른 일 양태에 따르면, R1은 치환 또는 비치환된 (C6-C30)아릴, 또는 치환된 (5-20원)헤테로아릴이다. 예를 들면, R1은 비치환된 페닐, 비치환된 비페닐, 비치환된 나프틸, 메틸로 치환된 플루오레닐, 메틸로 치환된 벤조플루오레닐, 비치환된 디벤조푸라닐, 비치환된 디벤조티오페닐, 스피로[플루오렌-플루오렌]일, 스피로[플루오렌-벤조플루오렌]일, 비치환된 피리딜 등일 수 있다.In Formula 1, R 1 is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl. According to an aspect of the present application, R 1 is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another aspect of the present application, R 1 is a substituted or unsubstituted (C6-C30)aryl, or a substituted (5-20 membered)heteroaryl. For example, R 1 is unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, methyl-substituted fluorenyl, methyl-substituted benzofluorenyl, unsubstituted dibenzofuranyl, unsubstituted cyclic dibenzothiophenyl, spiro[fluorene-fluoren]yl, spiro[fluorene-benzofluoren]yl, unsubstituted pyridyl, and the like.
상기 화학식 1에서, L1은 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이다. 본원의 일 양태에 따르면, L1은 단일결합, 또는 치환 또는 비치환된 (C6-C18)아릴렌이다. 본원의 다른 일 양태에 따르면, L1은 단일결합, 또는 비치환된 (C6-C12)아릴렌이다. 예를 들면, L1은 단일결합, 비치환된 페닐렌, 비치환된 나프틸렌 등일 수 있다.In Formula 1, L 1 is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene. According to an aspect of the present application, L 1 is a single bond, or a substituted or unsubstituted (C6-C18)arylene. According to another aspect of the present application, L 1 is a single bond, or an unsubstituted (C6-C12)arylene. For example, L 1 may be a single bond, unsubstituted phenylene, unsubstituted naphthylene, or the like.
상기 화학식 1 에서, Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이다. 본원의 일 양태에 따르면, Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 (C6-C25)아릴, 또는 치환 또는 비치환된 (3-20원)헤테로아릴이다. 본원의 다른 일 양태에 따르면, Ar1 및 Ar2는 각각 독립적으로 중수소, (C1-C6)알킬, (C6-C25)아릴, (3-20원)헤테로아릴, (C3-C7)시클로알킬 및 (C1-C6)알킬(C6-C12)아릴 중 하나 이상으로 치환 또는 비치환된 (C6-C25)아릴; 또는 (C6-C12)아릴 및 (5-15원)헤테로아릴 중 하나 이상으로 치환 또는 비치환된 (3-20원)헤테로아릴이다. 예를 들면, Ar1 및 Ar2는 각각 독립적으로 치환된 페닐, 나프틸, 비페닐, 페난트레닐, 디메틸플루오레닐, 디페닐플루오레닐, 나프틸페닐, 페닐나프틸, 디메틸벤조플루오레닐, 터페닐, 스피로비플루오레닐, 벤조푸라닐, 벤조티오페닐, 페닐로 치환 또는 비치환된 디벤조티오페닐, 페닐 또는 피리딜로 치환 또는 비치환된 디벤조푸라닐, 페닐로 치환된 카바졸릴, 벤조나프토푸라닐, 벤조나프토티오페닐, 벤조푸로피리딜 등일 수 있고; 상기 치환된 페닐의 치환기는 중수소, 메틸 및 tert-부틸 중 하나 이상으로 치환된 페닐; 안트라세닐; 플루오란테닐; 페닐플루오레닐; 시클로헥실; 페닐로 치환된 피리딜; 페녹사지닐; 및 페닐로 치환된 벤조이미다졸릴 중 하나 이상일 수 있다.In Formula 1, Ar 1 and Ar 2 are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl. According to an aspect of the present application, Ar 1 and Ar 2 are each independently a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3-20 membered)heteroaryl. According to another aspect of the present application, Ar 1 and Ar 2 are each independently deuterium, (C1-C6)alkyl, (C6-C25)aryl, (3-20 membered)heteroaryl, (C3-C7)cycloalkyl and (C6-C25)aryl unsubstituted or substituted with one or more of (C1-C6)alkyl(C6-C12)aryl; or (3-20 membered)heteroaryl which is unsubstituted or substituted with one or more of (C6-C12)aryl and (5-15 membered)heteroaryl. For example, Ar 1 and Ar 2 are each independently a substituted phenyl, naphthyl, biphenyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorene nyl, terphenyl, spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl unsubstituted or substituted with phenyl, dibenzofuranyl unsubstituted or substituted with phenyl or pyridyl, substituted with phenyl carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzofuropyridyl, and the like; The substituent of the substituted phenyl is phenyl substituted with one or more of deuterium, methyl and tert -butyl; anthracenyl; fluoranthenyl; phenylfluorenyl; cyclohexyl; pyridyl substituted with phenyl; phenoxazinyl; and phenyl-substituted benzimidazolyl.
상기 화학식 1 에서, R2 내지 R5는 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 또는 -L3-N(Ar3)(Ar4)이거나; 인접한 치환기끼리 서로 연결되어 고리를 형성할 수 있다. 본원의 일 양태에 따르면, R2 내지 R5는 각각 독립적으로 수소, 또는 치환 또는 비치환된 (C6-C12)아릴이다. 본원의 다른 일 양태에 따르면, R2 내지 R5는 각각 독립적으로 수소, 또는 비치환된 (C6-C12)아릴이다. 예를 들면, R2 및 R3은 수소일 수 있고, R4는 수소, 페닐 등일 수 있다.In Formula 1, R 2 to R 5 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted substituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30) ) arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L 3 -N(Ar 3 )(Ar 4 ); Adjacent substituents may be connected to each other to form a ring. According to an aspect of the present application, R 2 to R 5 are each independently hydrogen, or a substituted or unsubstituted (C6-C12)aryl. According to another aspect of the present application, R 2 to R 5 are each independently hydrogen or unsubstituted (C6-C12)aryl. For example, R 2 and R 3 may be hydrogen, and R 4 may be hydrogen, phenyl, or the like.
상기 화학식 1 에서, a는 1이고; b 및 c는 각각 독립적으로 1 또는 2이며, 바람직하게는 1이고; d는 1 내지 4 의 정수이고, 바람직하게는 1 또는 2이다. b 내지 d가 2 이상의 정수인 경우, 각각의 R2 내지 R4는 서로 동일하거나 상이할 수 있다.In Formula 1, a is 1; b and c are each independently 1 or 2, preferably 1; d is an integer of 1 to 4, preferably 1 or 2. When b to d are an integer of 2 or more, each of R 2 to R 4 may be the same as or different from each other.
본원의 일 양태에 따르면, 상기 화학식 1은 하기 화학식 1-1 내지 1-4 중 하나 이상으로 표시될 수 있다.According to an aspect of the present application, Chemical Formula 1 may be represented by one or more of the following Chemical Formulas 1-1 to 1-4.
[화학식 1-1] [화학식 1-2][Formula 1-1] [Formula 1-2]
[화학식 1-3] [화학식 1-4][Formula 1-3] [Formula 1-4]
상기 화학식 1-1 내지 1-4에서, R1 내지 R4, Ar1, Ar2, L1 및 a 내지 d는 화학식 1에서 정의된 것과 같다.In Formulas 1-1 to 1-4, R 1 to R 4 , Ar 1 , Ar 2 , L 1 , and a to d are the same as defined in Formula 1.
상기 화학식 2로 표시되는 화합물에 대해 보다 구체적으로 설명하면 다음과 같다.The compound represented by Formula 2 will be described in more detail as follows.
상기 화학식 2에서, HAr은 각각 독립적으로 치환 또는 비치환된 질소 함유 (3-20원)헤테로아릴이다. 본원의 일 양태에 따르면, HAr은 각각 독립적으로 치환 또는 비치환된 질소 함유 (5-15원)헤테로아릴이다. 본원의 다른 일 양태에 따르면, HAr은 각각 독립적으로 중수소; (C1-C6)알킬; 중수소, (C1-C6)알킬 및 (C6-C12)아릴 중 하나 이상으로 치환 또는 비치환된 (C6-C20)아릴; (C6-C12)아릴로 치환 또는 비치환된 (5-15원)헤테로아릴; (C1-C6)알킬(C6-C20)아릴 중 하나 이상으로 치환 또는 비치환된 질소 함유 (5-15원)헤테로아릴이다. 예를 들면, HAr은 각각 독립적으로 치환 또는 비치환된 트리아지닐, 치환 또는 비치환된 피리딜, 치환 또는 비치환된 피리미디닐, 치환 또는 비치환된 퀴나졸리닐, 치환 또는 비치환된 벤조퀴나졸리닐, 치환 또는 비치환된 퀴녹살리닐, 치환 또는 비치환된 벤조퀴녹살리닐, 치환 또는 비치환된 퀴놀릴, 치환 또는 비치환된 벤조퀴놀릴, 치환 또는 비치환된 이소퀴놀릴, 치환 또는 비치환된 벤조이소퀴놀릴, 치환 또는 비치환된 카바졸릴, 치환 또는 비치환된 트리아졸릴, 치환 또는 비치환된 피라졸릴, 치환 또는 비치환된 나프티리디닐, 치환 또는 비치환된 트리아자나프틸, 치환 또는 비치환된 벤조푸로피리미디닐, 또는 치환 또는 비치환된 벤조티에노피리미디닐 등일 수 있고, 상기 치환기는 중수소, 메틸, 페닐, 하나 이상의 중수소로 치환된 페닐, 나프틸페닐, 나프틸, 페닐나프틸, 비페닐, 디메틸플루오레닐, 디페닐플루오레닐, 페난트레닐, 플루오란테닐, 터페닐, 크라이세닐, 트리페닐레닐, 페닐피리딜, 디벤조푸라닐, 디벤조티오페닐, 페닐카바졸릴 중 하나 이상일 수 있다.In Formula 2, HAr is each independently a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl. According to one aspect of the present application, each HAr is independently a substituted or unsubstituted nitrogen-containing (5-15 membered) heteroaryl. According to another aspect of the present application, HAr are each independently deuterium; (C1-C6)alkyl; (C6-C20)aryl unsubstituted or substituted with one or more of deuterium, (C1-C6)alkyl and (C6-C12)aryl; (5-15 membered) heteroaryl unsubstituted or substituted with (C6-C12)aryl; It is a nitrogen-containing (5-15 membered) heteroaryl unsubstituted or substituted with one or more of (C1-C6)alkyl(C6-C20)aryl. For example, each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquina Jolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or Unsubstituted benzoisoquinolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted triazanaphthyl , substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl, and the like, wherein the substituents are deuterium, methyl, phenyl, phenyl substituted with one or more deuterium, naphthylphenyl, naph Tyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, phenanthrenyl, fluoranthenyl, terphenyl, chrysenyl, triphenylenyl, phenylpyridyl, dibenzofuranyl, dibenzothio It may be at least one of phenyl and phenylcarbazolyl.
상기 화학식 2에서, L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이다. 본원의 일 양태에 따르면, L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C15)아릴렌, 또는 치환 또는 비치환된 (5-15원)헤테로아릴렌이다. 본원의 다른 일 양태에 따르면, L11은 각각 독립적으로 단일결합, (C6-C12)아릴로 치환 또는 비치환된 (C6-C15)아릴렌, 또는 비치환된 (5-15원)헤테로아릴렌이다. 예를 들면, L11은 각각 독립적으로 단일결합, 페닐렌, 나프틸렌, 비페닐렌, 페닐로 치환된 페닐렌, 디벤조푸라닐렌 등일 수 있다.In Formula 2, L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene. According to an aspect of the present application, L 11 is each independently a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted (5-15 membered)heteroarylene. According to another embodiment of the present application, each L 11 is independently a single bond, (C6-C12) aryl-substituted or unsubstituted (C6-C15) arylene, or unsubstituted (5-15 membered) heteroarylene to be. For example, each L 11 may independently be a single bond, phenylene, naphthylene, biphenylene, phenyl substituted phenylene, dibenzofuranylene, or the like.
상기 화학식 2에서, Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이다.In Formula 2, Ar 11 is each independently any one of Formulas 3 to 5 below.
[화학식 3] [화학식 4] [화학식 5][Formula 3] [Formula 4] [Formula 5]
상기 화학식 3 내지 5에서, Y2는 O 또는 S이다.In Formulas 3 to 5, Y 2 is O or S.
상기 화학식 3 내지 5에서, R20 내지 R29은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 또는 -L3-N(Ar3)(Ar4)이다. 본원의 일 양태에 따르면, R20 내지 R29은 각각 독립적으로 수소, 치환 또는 비치환된 (C6-C20)아릴, 또는 치환 또는 비치환된 (5-15원)헤테로아릴이다. 본원의 다른 일 양태에 따르면, R20 내지 R29은 각각 독립적으로 수소; 중수소, 시아노, (C6-C12)아릴 및 (5-15원)헤테로아릴 중 하나 이상으로 치환 또는 비치환된 (C6-C20)아릴; 또는 (C6-C12)아릴로 치환 또는 비치환된 (5-15원)헤테로아릴이다. 예를 들면, R20 내지 R29은 각각 독립적으로 수소, 페닐, 하나 이상의 중수소로 치환된 페닐, 시아노로 치환된 페닐, 나프틸페닐, 디벤조티오페닐로 치환된 페닐, 나프틸, 페닐나프틸, 비페닐, 하나 이상의 시아노로 치환된 비페닐, 페난트레닐, 피리딜, 페닐로 치환된 피리딜, 이소퀴놀릴, 페닐로 치환된 카바졸릴, 디벤조푸라닐, 디벤조티오페닐 등일 수 있다.In Formulas 3 to 5, R 20 to R 29 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkyl Silyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6 -C30) arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L 3 -N(Ar 3 )(Ar 4 ). According to an aspect of the present application, R 20 to R 29 are each independently hydrogen, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5-15 membered)heteroaryl. According to another aspect of the present application, R 20 To R 29 They are each independently hydrogen; (C6-C20)aryl unsubstituted or substituted with one or more of deuterium, cyano, (C6-C12)aryl and (5-15 membered)heteroaryl; or (5-15 membered)heteroaryl unsubstituted or substituted with (C6-C12)aryl. For example, R 20 to R 29 are each independently hydrogen, phenyl, phenyl substituted with one or more deuterium, phenyl substituted with cyano, naphthylphenyl, phenyl substituted with dibenzothiophenyl, naphthyl, phenylnaphthyl , biphenyl, biphenyl substituted with one or more cyano, phenanthrenyl, pyridyl, pyridyl substituted with phenyl, isoquinolyl, carbazolyl substituted with phenyl, dibenzofuranyl, dibenzothiophenyl, etc. .
상기 화학식 2에서, e는 1 또는 2이며, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있다.In Formula 2, e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other.
상기 화학식 3 내지 5에서, *는 L11와 연결되는 위치를 나타낸다.In Formulas 3 to 5, * represents a position connected to L 11 .
상기 화학식 1 및 3 내지 5에서, L3은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이다.In Formulas 1 and 3 to 5, L 3 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene.
상기 화학식 1 및 3 내지 5에서, Ar3 및 Ar4는 각각 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이다.In Formulas 1 and 3 to 5, Ar 3 and Ar 4 are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted A fused ring group of an aliphatic ring of (C3-C30) and an aromatic ring of (C6-C30), a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.
상기 화학식 1로 표시되는 화합물은 하기의 화합물들로부터 선택되는 하나 이상일 수 있으나, 이들에 한정되는 것은 아니다.The compound represented by Formula 1 may be one or more selected from the following compounds, but is not limited thereto.
상기 화학식 2로 표시되는 화합물은 하기의 화합물들로부터 선택되는 하나 이상일 수 있으나, 이들에 한정되는 것은 아니다.The compound represented by Formula 2 may be one or more selected from the following compounds, but is not limited thereto.
상기 화합물 H1-1 내지 H1-136 중 하나 이상과 상기 화합물 C-1 내지 C-127 중 하나 이상이 조합되어 유기 전계 발광 소자에 사용될 수 있다.At least one of the compounds H1-1 to H1-136 and at least one of the compounds C-1 to C-127 may be combined to be used in an organic electroluminescent device.
본원에 따른 화학식 1로 표시되는 화합물은 당업자에게 공지된 합성 방법으로 제조할 수 있으며, 예를 들면, 한국 공개특허공보 제10-2017-0022865호 (2017.03.02 공개), 한국 공개특허공보 제10-2017-0051198호 (2017.05.11 공개), 한국 공개특허공보 제10-2018-0094572호 (2018.08.24 공개) 등을 참조하여 제조할 수 있으나, 이에 한정되지는 않는다.The compound represented by Formula 1 according to the present application may be prepared by a synthetic method known to those skilled in the art, for example, Korean Patent Application Laid-Open No. 10-2017-0022865 (published on Mar. 02, 2017), Korean Patent Application Laid-Open No. 10 -2017-0051198 (published on May 11, 2017), may be manufactured with reference to Korean Patent Application Laid-Open No. 10-2018-0094572 (published on August 24, 2018), but is not limited thereto.
본원에 따른 화학식 2로 표시되는 화합물은 당업자에게 공지된 합성 방법으로 제조할 수 있으며, 예를 들면, 하기 반응식 1 내지 3을 참조하여 제조할 수 있으나, 이에 한정되지는 않는다.The compound represented by Formula 2 according to the present application may be prepared by a synthetic method known to those skilled in the art, for example, may be prepared with reference to the following Schemes 1 to 3, but is not limited thereto.
[반응식 1][Scheme 1]
[반응식 2][Scheme 2]
[반응식 3][Scheme 3]
상기 반응식 1 내지 3에서, Y2, R20 내지 R29, L11, HAr 및 e는 화학식 2에서의 정의와 동일하고, Hal은 할로겐 원자이다.In Schemes 1 to 3, Y 2 , R 20 to R 29 , L 11 , HAr and e are the same as defined in Formula 2, and Hal is a halogen atom.
상기에서 본원 화학식 2로 표시되는 화합물의 예시적 합성예를 설명하였지만, 이들은 모두 Buchwald-Hartwig cross coupling 반응, N-arylation 반응, H-mont-mediated etherification 반응, Miyaura borylation 반응, Suzuki cross-coupling 반응, Intramolecular acid-induced cyclization 반응, Pd(II)-catalyzed oxidative cyclization 반응, Grignard 반응, Heck 반응, Cyclic Dehydration 반응, SN1 치환 반응, SN2 치환 반응, 및 Phosphine-mediated reductive cyclization 반응 등에 기초한 것으로 구체적 합성예에 명시된 치환기 이외에 화학식 2에 정의된 다른 치환기가 결합되더라도 상기 반응이 진행된다는 것을 당업자라면 쉽게 이해할 수 있을 것이다.Although exemplary synthesis examples of the compound represented by Formula 2 have been described above, these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Specific synthesis examples based on intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN 1 substitution reaction, SN 2 substitution reaction, and Phosphine-mediated reductive cyclization reaction It will be readily understood by those skilled in the art that the reaction proceeds even if other substituents defined in Formula 2 are combined in addition to the substituents specified in .
본원에 따른 유기 전계 발광 소자는 양극, 음극 및 상기 양극과 상기 음극 사이에 적어도 1층의 유기물층을 포함하고, 상기 유기물층은 제1 유기 전계 발광 재료로 상기 화학식 1로 표시되는 화합물, 및 제2 유기 전계 발광 재료로 상기 화학식 2로 표시되는 화합물을 포함하는 복수 종의 유기 전계 발광 재료를 포함할 수 있다. 본원의 일 양태에 따르면, 본원에 따른 유기 전계 발광 소자는 양극, 음극, 및 상기 양극과 상기 음극 사이에 적어도 1층의 발광층을 포함하고, 상기 발광층은 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물을 포함할 수 있다.The organic electroluminescent device according to the present application includes an anode, a cathode, and at least one organic material layer between the anode and the cathode, wherein the organic material layer is a first organic electroluminescent material as a compound represented by Formula 1, and a second organic material layer The electroluminescent material may include a plurality of organic electroluminescent materials including the compound represented by Formula 2 above. According to an aspect of the present application, the organic electroluminescent device according to the present application includes an anode, a cathode, and at least one light emitting layer between the anode and the cathode, and the light emitting layer is a compound represented by Formula 1 and Formula 2 It may contain a compound that is
상기 발광층은 호스트와 도판트를 포함하고, 상기 호스트는 복수종의 호스트 재료를 포함하며, 상기 화학식 1로 표시되는 화합물은 복수종의 호스트 재료 중 제1 호스트 화합물로, 상기 화학식 2로 표시되는 화합물은 복수종의 호스트 재료 중 제2 호스트 화합물로 포함될 수 있다. 여기서, 제1 호스트 화합물과 제 2 호스트 화합물의 중량비는 약 1:99 내지 약 99:1, 바람직하게는 약 10:90 내지 약 90:10, 더욱 바람직하게는 약 30:70 내지 약 70:30, 더욱 바람직하게는 약 40:60 내지 약 60:40이며, 더욱 더 바람직하게는 약 50:50이다.The light emitting layer includes a host and a dopant, the host includes a plurality of host materials, and the compound represented by Formula 1 is a first host compound among the plurality of host materials, and the compound represented by Formula 2 may be included as the second host compound among the plurality of types of host materials. Here, the weight ratio of the first host compound to the second host compound is from about 1:99 to about 99:1, preferably from about 10:90 to about 90:10, more preferably from about 30:70 to about 70:30 , more preferably about 40:60 to about 60:40, and even more preferably about 50:50.
본원에서 발광층은 발광이 이루어지는 층으로서 단일층일 수 있으며, 또한 2개 이상의 층이 적층된 복수의 층일 수 있다. 본원의 복수 종의 호스트 재료는 제1 및 제2 호스트 재료가 모두 하나의 층에 포함될 수도 있고, 제1 및 제2 호스트 재료가 각각 다른 발광층에 포함될 수도 있다. 본원의 일 태양에 따르면, 상기 발광층의 호스트 화합물에 대한 도판트 화합물의 도핑 농도는 20 중량% 미만일 수 있다.The light emitting layer herein may be a single layer as a layer that emits light, or may be a plurality of layers in which two or more layers are stacked. In the plurality of host materials of the present disclosure, both the first and second host materials may be included in one layer, and the first and second host materials may be included in different light emitting layers, respectively. According to one aspect of the present application, the doping concentration of the dopant compound with respect to the host compound of the emission layer may be less than 20% by weight.
본원의 유기 전계 발광 소자는 정공주입층, 정공전달층, 정공보조층, 발광보조층, 전자전달층, 전자주입층, 계면층(interlayer), 전자버퍼층, 정공차단층 및 전자차단층에서 선택되는 1층 이상을 더 포함할 수 있다. 본원의 일 양태에 따르면, 본원의 유기 전계 발광 소자는 본원의 복수 종의 호스트 재료 이외에 아민계 화합물을 정공 주입 재료, 정공 전달 재료, 정공 보조 재료, 발광 재료, 발광 보조 재료, 및 전자 차단 재료 중 하나 이상으로 더 포함할 수 있다. 또한, 본원의 일 양태에 따르면, 본원의 유기 전계 발광 소자는 본원의 복수 종의 호스트 재료 이외에 아진계 화합물을 전자 전달 재료, 전자 주입 재료, 전자 버퍼 재료 및 정공 차단 재료 중 하나 이상으로 더 포함할 수 있다.The organic electroluminescent device of the present application is selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, an electron buffer layer, a hole blocking layer and an electron blocking layer. It may further include one or more floors. According to one aspect of the present application, the organic electroluminescent device of the present application includes an amine compound in addition to a plurality of host materials of the present application, among a hole injection material, a hole transport material, a hole auxiliary material, a light emitting material, a light emitting auxiliary material, and an electron blocking material. It may further include one or more. In addition, according to one aspect of the present application, the organic electroluminescent device of the present application may further include a azine-based compound as one or more of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material in addition to a plurality of host materials of the present application. can
본원에 따른 복수 종의 호스트 재료는 백색 유기 전계 발광 소자(White Organic Light Emitting Device)를 위한 발광 재료로서 사용될 수 있다. 상기 백색 유기 전계 발광 소자는 R(적색), G(녹색) 또는 YG(황녹색), B(청색) 발광부들의 배열 형태에 따라 병렬 배치(side-by-side) 방식, 적층(stacking) 방식, 또는 색 변환 물질(color conversion material, CCM) 방식 등 다양한 구조들이 제안되고 있다. 또한 일 예에 따른 복수 종의 호스트 재료는 양자점(QD)을 포함하는 유기 전계 발광 소자에도 사용될 수 있다.A plurality of types of host materials according to the present disclosure may be used as a light emitting material for a white organic light emitting device (White Organic Light Emitting Device). The white organic EL device is a side-by-side method, a stacking method, depending on the arrangement of R (red), G (green) or YG (yellow green), B (blue) light emitting units , or various structures such as a color conversion material (CCM) method have been proposed. In addition, a plurality of host materials according to an example may be used in an organic electroluminescent device including quantum dots (QDs).
양극과 발광층 사이에 정공 주입층, 정공 전달층, 전자 차단층, 또는 이들의 조합이 사용될 수 있다. 정공 주입층은 양극에서 정공 전달층 또는 전자 차단층으로의 정공 주입 장벽(또는 정공 주입 전압)을 낮출 목적으로 복수의 층이 사용될 수 있으며, 각 층은 2개의 화합물이 동시에 사용될 수 있다. 또한 상기 정공 주입층은 p-도판트로 도핑될 수 있다. 전자 차단층은 정공 전달층(또는 정공 주입층)과 발광층 사이에 위치하고, 발광층으로부터의 전자의 오버플로우를 차단하여 엑시톤을 발광층 내에 가두어 발광 누수를 방지할 수 있다. 정공 전달층 또는 전자 차단층은 복수의 층이 사용될 수 있고, 각 층에 복수의 화합물이 사용될 수 있다.A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. In the hole injection layer, a plurality of layers may be used for the purpose of lowering the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, and two compounds may be used in each layer at the same time. In addition, the hole injection layer may be doped with a p-dopant. The electron blocking layer is positioned between the hole transport layer (or hole injection layer) and the light emitting layer, and blocks the overflow of electrons from the light emitting layer to trap excitons in the light emitting layer, thereby preventing light emission leakage. A plurality of layers may be used for the hole transport layer or the electron blocking layer, and a plurality of compounds may be used for each layer.
발광층과 음극 사이에 전자 버퍼층, 정공 차단층, 전자 전달층, 전자 주입층, 또는 이들의 조합이 사용될 수 있다. 전자 버퍼층은 전자주입을 조절하고 발광층과 전자 주입층 사이의 계면 특성을 향상시킬 목적으로 복수의 층이 사용될 수 있으며, 각 층은 2개의 화합물이 동시에 사용될 수 있다. 정공 차단층 또는 전자 전달층도 복수의 층이 사용될 수 있고, 각 층에 복수의 화합물이 사용될 수 있다. 또한, 상기 전자 주입층은 n-도판트로 도핑될 수 있다.An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. In the electron buffer layer, a plurality of layers may be used for the purpose of controlling electron injection and improving interfacial properties between the light emitting layer and the electron injection layer, and two compounds may be used for each layer at the same time. A plurality of layers may be used for the hole blocking layer or the electron transport layer, and a plurality of compounds may be used for each layer. In addition, the electron injection layer may be doped with an n-dopant.
본원의 유기 전계 발광 소자에 포함되는 도판트로는 하나 이상의 인광 또는 형광 도판트를 사용할 수 있고, 인광 도판트가 바람직하다. 본원의 유기 전계 발광 소자에 적용되는 인광 도판트 재료는 특별히 제한되지는 않으나, 이리듐(Ir), 오스뮴(Os), 구리(Cu) 및 백금(Pt)으로부터 선택되는 금속 원자의 착체 화합물일 수 있고, 경우에 따라 바람직하게는, 이리듐(Ir), 오스뮴(Os), 구리(Cu) 및 백금(Pt)으로부터 선택되는 금속 원자의 오르토 메탈화 착체 화합물일 수 있으며, 경우에 따라 더 바람직하게는, 오르토 메탈화 이리듐 착체 화합물일 수 있다.As a dopant included in the organic electroluminescent device of the present application, one or more phosphorescent or fluorescent dopants may be used, and a phosphorescent dopant is preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present application is not particularly limited, but may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt). , optionally, it may be an ortho-metalation complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases more preferably, ortho-metalated iridium complex compounds.
본원의 유기 전계 발광 소자에 포함되는 도판트로 하기 화학식 101로 표시되는 화합물을 사용할 수 있으나, 이에 한정되지는 않는다.As a dopant included in the organic electroluminescent device of the present application, a compound represented by the following Chemical Formula 101 may be used, but is not limited thereto.
[화학식 101][Formula 101]
상기 화학식 101에서,In Formula 101,
L'은 하기 구조 1 내지 3 중에서 선택되고;L' is selected from the following structures 1 to 3;
[구조 1] [구조 2] [구조 3][Structure 1] [Structure 2] [Structure 3]
R100 내지 R103은 각각 독립적으로 수소, 중수소, 할로겐, 중수소 및/또는 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C6-C30)아릴, 시아노, 치환 또는 비치환된 (3-30원)헤테로아릴, 또는 치환 또는 비치환된 (C1-C30)알콕시이거나; 인접한 치환기와 연결되어 고리를 형성할 수 있고, 예를 들면 피리딘과 함께 치환 또는 비치환된 퀴놀린, 치환 또는 비치환된 이소퀴놀린, 치환 또는 비치환된 벤조푸로피리딘, 치환 또는 비치환된 벤조티에노피리딘, 치환 또는 비치환된 인데노피리딘, 치환 또는 비치환된 벤조푸로퀴놀린, 치환 또는 비치환된 벤조티에노퀴놀린, 또는 치환 또는 비치환된 인데노퀴놀린을 형성할 수 있으며;R 100 to R 103 are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; It may be linked with adjacent substituents to form a ring, for example, together with pyridine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothieno pyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;
R104 내지 R107은 각각 독립적으로 수소, 중수소, 할로겐, 중수소 및/또는 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 시아노, 또는 치환 또는 비치환된 (C1-C30)알콕시이거나; 인접한 치환기와 연결되어 고리를 형성할 수 있고, 예를 들면 벤젠과 함께 치환 또는 비치환된 나프탈렌, 치환 또는 비치환된 플루오렌, 치환 또는 비치환된 디벤조티오펜, 치환 또는 비치환된 디벤조푸란, 치환 또는 비치환된 인데노피리딘, 치환 또는 비치환된 벤조푸로피리딘, 또는 치환 또는 비치환된 벤조티에노피리딘을 형성할 수 있으며;R 104 to R 107 are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; It may be linked with adjacent substituents to form a ring, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzo together with benzene furan, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine;
R201 내지 R220은 각각 독립적으로 수소, 중수소, 할로겐, 중수소 및/또는 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 또는 치환 또는 비치환된 (C6-C30)아릴이거나; 인접한 치환기와 연결되어 고리를 형성할 수 있으며;R 201 to R 220 are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, or substituted or unsubstituted cyclic (C6-C30)aryl; may be linked with adjacent substituents to form a ring;
s은 1 내지 3의 정수이다.s is an integer from 1 to 3.
구체적으로, 상기 도판트 화합물의 구체적인 예는 다음과 같으나, 이에 한정되지는 않는다.Specifically, specific examples of the dopant compound are as follows, but are not limited thereto.
본원의 유기 전계 발광 소자의 각 층은 진공 증착, 스퍼터링, 플라즈마, 이온 플레이팅 등의 건식 성막법이나, 잉크 젯 프린팅(ink jet printing), 노즐 프린팅(nozzle printing), 슬롯 코팅(slot coating), 스핀 코팅, 침지 코팅(dip coating), 플로우 코팅 등의 습식 성막법 중 어느 하나의 방법으로 형성될 수 있다.Each layer of the organic electroluminescent device of the present application is a dry film deposition method such as vacuum deposition, sputtering, plasma, ion plating, ink jet printing, nozzle printing, slot coating, It may be formed by any one of a wet film forming method such as spin coating, dip coating, flow coating, or the like.
습식 성막법의 경우, 각 층을 형성하는 재료를 에탄올, 클로로포름, 테트라하이드로푸란, 디옥산 등의 적절한 용매에 용해 또는 분산시켜 박막을 형성하는데, 그 용매는 각 층을 형성하는 재료가 용해 또는 분산될 수 있고, 성막성에 문제가 없는 것이라면 어느 것이어도 된다.In the case of the wet film forming method, a thin film is formed by dissolving or dispersing the material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, the solvent in which the material forming each layer is dissolved or dispersed. It can be, and any one may be used as long as there is no problem in the film-forming property.
또한, 본원의 제1 및 제2 호스트 화합물을 상기 열거된 방법으로 성막할 수 있으며, 흔히 공증착 또는 혼합증착 공정에 의해 성막할 수 있다. 상기 공증착은 두 가지 이상의 재료를 각각의 개별 도가니 소스에 넣고, 두 셀을 동시에 전류를 인가하여 재료를 증발시켜 혼합 증착하는 방식이고, 상기 혼합 증착은 증착 전 두 가지 이상의 재료를 하나의 도가니 소스에 혼합한 후, 하나의 셀에 전류를 인가하여 재료를 증발시켜 혼합 증착하는 방식이다. 또한, 제1 및 제2 호스트 화합물이 유기 전계 발광 소자 내의 같은 층 또는 다른 층에 존재하게 되는 경우, 두 호스트 화합물은 각각 개별적으로 성막할 수 있다. 예를 들어, 제1 호스트 화합물을 증착한 후 제2 호스트 화합물을 증착할 수 있다.In addition, the first and second host compounds of the present application can be formed by the methods listed above, and can often be formed by a co-deposition or mixed vapor deposition process. The co-deposition is a method of mixing two or more materials by putting two or more materials into each individual crucible source, evaporating the materials by applying an electric current to both cells at the same time, and performing mixed deposition. After mixing, a current is applied to one cell to evaporate the material, and mixed deposition is performed. In addition, when the first and second host compounds are present in the same layer or in different layers in the organic electroluminescent device, the two host compounds may be individually formed. For example, after depositing the first host compound, the second host compound may be deposited.
본원은 상기 화학식 2' 또는 화학식 2"로 표시되는 유기 전계 발광 화합물을 이용하거나, 상기 화학식 1 로 표시되는 화합물 및 상기 화학식 2로 표시되는 화합물을 포함하는 복수 종의 호스트 재료를 이용하여 디스플레이 장치를 제공할 수 있다. 즉, 본원의 화학식 2' 또는 화학식 2"로 표시되는 유기 전계 발광 화합물을 이용하거나, 복수 종의 호스트 재료를 이용하여 표시 장치 또는 조명 장치를 제조하는 것이 가능하다. 구체적으로, 디스플레이 장치, 예를 들면, 백색 유기 발광 소자(White Organic Light Emitting Device), 스마트폰, 태블릿, 노트북, PC, TV 또는 차량용의 디스플레이 장치, 또는 조명 장치, 예를 들면, 옥외 또는 옥내용 조명 장치를 제조하는 것이 가능하다.The present application uses the organic electroluminescent compound represented by Formula 2' or Formula 2", or a display device using a plurality of host materials including the compound represented by Formula 1 and the compound represented by Formula 2 That is, it is possible to manufacture a display device or a lighting device using the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present application, or using a plurality of host materials. Specifically, a display device, for example, a white organic light emitting device (White Organic Light Emitting Device), a display device for a smartphone, tablet, notebook, PC, TV or vehicle, or a lighting device, for example, for outdoor or indoor use It is possible to manufacture a lighting device.
이하에서, 본원의 상세한 이해를 위하여 본원의 대표 화합물을 들어 본원에 따른 화합물의 제조방법 및 이의 물성, 그리고 본원의 복수 종의 호스트 재료를 포함하는 OLED의 특성에 대해 살펴본다. 그러나, 이하의 실시예는 본원의 상세한 이해를 위하여 본원에 따른 화합물 및 본원에 따른 복수 종의 호스트 재료를 포함하는 OLED의 특성을 설명한 것일 뿐, 본원은 하기의 예들에 한정되는 것은 아니다.Hereinafter, for a detailed understanding of the present application, for a detailed understanding of the present application, a method for preparing a compound according to the present application, a method for preparing a compound according to the present application, physical properties thereof, and characteristics of an OLED including a plurality of host materials of the present application will be described. However, the following Examples only describe the properties of an OLED including a compound according to the present application and a plurality of host materials according to the present application for a detailed understanding of the present application, and the present application is not limited to the following examples.
[합성예 1] 화합물 H1-27의 제조[Synthesis Example 1] Preparation of compound H1-27
1) 화합물 1의 합성1) Synthesis of compound 1
플라스크에 디벤조푸란-2-아민 (20 g, 144.7 mmol), 2-브로모 디벤조푸란 (23.8 g, 96.47 mmol), Pd(OAc)2 (1.1 g, 4.82 mmol), 2-디사이클로헥실포스피노-2',6'-디메톡시비페닐(S-Phos) (3.9 g, 9.65 mmol), NaOt-Bu (13.9 g, 144.7 mmol) 및 o-자일렌 485 mL를 넣고 160℃에서 3시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 1 (4.9 g, 수율: 10%)를 얻었다.In a flask, dibenzofuran-2-amine (20 g, 144.7 mmol), 2-bromo dibenzofuran (23.8 g, 96.47 mmol), Pd(OAc) 2 (1.1 g, 4.82 mmol), 2-dicyclohexyl Phosphino-2',6'-dimethoxybiphenyl (S-Phos) (3.9 g, 9.65 mmol), NaOt-Bu (13.9 g, 144.7 mmol) and 485 mL of o-xylene were added, and 3 hours at 160 °C. stirred for a while. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 1 (4.9 g, yield: 10%).
2) 화합물 H1-27의 합성2) Synthesis of compound H1-27
플라스크에 화합물 1 (4.9 g, 12.76 mmol), 화합물 2 (4.2 g, 14.0 mmol), Pd(dba3)2 (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol) 및 o-자일렌 65 mL를 넣고 160℃에서 2시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 H1-27 (5.6 g, 수율: 68.3%)를 얻었다.In a flask, put compound 1 (4.9 g, 12.76 mmol), compound 2 (4.2 g, 14.0 mmol), Pd(dba 3 ) 2 (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol) and 65 mL of o-xylene were added and stirred at 160° C. for 2 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-27 (5.6 g, yield: 68.3%). .
[합성예 2] 화합물 H1-46의 제조[Synthesis Example 2] Preparation of compound H1-46
플라스크에 화합물 3 (25 g, 74.48 mmol), 화합물 2 (42.58 g, 81.93 mmol), Pd(OAc)2 (0.16 g, 7.5 mmol), P(t-Bu)3 (0.28 g, 7.5 mmol), NaOt-Bu (14.31 g, 150 mmol) 및 o-자일렌 284.09 mL를 넣고, 160℃에서 2시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 H1-46 (23.4 g, 수율: 50%)를 얻었다.In a flask, compound 3 (25 g, 74.48 mmol), compound 2 (42.58 g, 81.93 mmol), Pd(OAc) 2 (0.16 g, 7.5 mmol), P(t-Bu) 3 (0.28 g, 7.5 mmol), NaOt-Bu (14.31 g, 150 mmol) and 284.09 mL of o-xylene were added, and the mixture was stirred at 160° C. for 2 hours. After completion of the reaction, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-46 (23.4 g, yield: 50%). .
[합성예 3] 화합물 H1-43의 제조[Synthesis Example 3] Preparation of compound H1-43
플라스크에 화합물 4 (20 g, 56.96 mmol), 화합물 2 (18.8 g, 57.13 mmol), Pd(OAc)2 (0.13 g, 5.7 mmol), P(t-Bu)3 (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol) 및 o-자일렌 227.27 mL를 넣고, 160℃에서 2시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 H1-43 (12.5 g, 수율: 34%)를 얻었다.In a flask, compound 4 (20 g, 56.96 mmol), compound 2 (18.8 g, 57.13 mmol), Pd(OAc) 2 (0.13 g, 5.7 mmol), P(t-Bu) 3 (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol) and 227.27 mL of o-xylene were added, and the mixture was stirred at 160° C. for 2 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-43 (12.5 g, yield: 34%). .
[합성예 4] 화합물 H1-123의 제조[Synthesis Example 4] Preparation of compound H1-123
1) 화합물 5의 합성1) Synthesis of compound 5
플라스크에 3-아미노비페닐 (54 g, 319 mmol), 3-브로모비페닐 (70 g, 301 mmol), Pd(OAc)2 (0.33 g, 1.47 mmol), 트리시클로헥실포스핀 (0.84 g, 2.8 mmol), NaOt-Bu (57 g, 593 mmol) 및 톨루엔 280 mL를 넣고 95℃에서 8시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 5 (60.23 g, 수율: 85%)을 얻었다.In a flask, 3-aminobiphenyl (54 g, 319 mmol), 3-bromobiphenyl (70 g, 301 mmol), Pd(OAc) 2 (0.33 g, 1.47 mmol), tricyclohexylphosphine (0.84 g, 2.8 mmol), NaOt-Bu (57 g, 593 mmol) and 280 mL of toluene were added and stirred at 95° C. for 8 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 5 (60.23 g, yield: 85%).
2) 화합물 H1-123의 합성2) Synthesis of compound H1-123
플라스크에 화합물 5 (60.23 g, 187.5 mmol), 화합물 2 (60 g, 182.33 mmol), Pd(OAc)2 (0.41 g, 1.83 mmol), S-phos (1.74 g, 4.23 mmol), NaOt-Bu (26.23 g, 272 mmol) 및 자일렌 300 mL를 넣고 110℃에서 10시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 H1-123 (36.9 g, 수율: 33%)를 얻었다.In a flask, compound 5 (60.23 g, 187.5 mmol), compound 2 (60 g, 182.33 mmol), Pd(OAc) 2 (0.41 g, 1.83 mmol), S-phos (1.74 g, 4.23 mmol), NaOt-Bu ( 26.23 g, 272 mmol) and 300 mL of xylene were added and stirred at 110° C. for 10 hours. After completion of the reaction, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-123 (36.9 g, yield: 33%). .
[합성예 5] 화합물 H1-136의 제조[Synthesis Example 5] Preparation of compound H1-136
1) 화합물 6의 합성1) Synthesis of compound 6
플라스크에 디벤조푸란-2-아민 (29.24 g, 159.7 mmol), 2-브로모디벤조티오펜 (40 g, 152.7 mmol), Pd(OAc)2 (0.17 g, 0.75 mmol), 트리시클로헥실포스핀 (0.43 g, 1.45 mmol), NaOt-Bu (29.22 g, 304 mmol) 및 톨루엔 250 mL를 넣고 95℃에서 8시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 6 (17.12 g, 수율: 86%)을 얻었다.Dibenzofuran-2-amine (29.24 g, 159.7 mmol), 2-bromodibenzothiophene (40 g, 152.7 mmol), Pd(OAc) 2 (0.17 g, 0.75 mmol), tricyclohexylphosphine in a flask (0.43 g, 1.45 mmol), NaOt-Bu (29.22 g, 304 mmol) and 250 mL of toluene were added and stirred at 95°C for 8 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound 6 (17.12 g, yield: 86%).
2) 화합물 H1-136의 합성2) Synthesis of compound H1-136
플라스크에 화합물 6 (17.12 g, 46.89 mmol), 화합물 2 (15 g, 45.58 mmol), Pd(OAc)2 (0.05 g, 0.22 mmol), S-phos (0.22 g, 0.535 mmol), NaOt-Bu (6.56 g, 68.2 mmol) 및 자일렌 75 mL를 넣고 110℃에서 10시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 H1-136 (10.2 g, 수율: 34%)을 얻었다.In a flask, compound 6 (17.12 g, 46.89 mmol), compound 2 (15 g, 45.58 mmol), Pd(OAc) 2 (0.05 g, 0.22 mmol), S-phos (0.22 g, 0.535 mmol), NaOt-Bu ( 6.56 g, 68.2 mmol) and 75 mL of xylene were added and stirred at 110° C. for 10 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-136 (10.2 g, yield: 34%). .
[합성예 6] 화합물 H1-85의 제조[Synthesis Example 6] Preparation of compound H1-85
플라스크에 화합물 2 (5.0 g, 15.2 mmol), 디([1,1'-비페닐]-4-일)아민 (4.9 g, 15.2 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), P(t-Bu)3 (0.8 mL, 1.5 mmol), NaOt-Bu (2.9 g, 30.4 mmol) 및 자일렌 76 mL를 넣고, 160℃에서 5시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 석출된 고체를 증류수와 메탄올로 씻어주었다. 이후 컬럼 크로마토그래피로 분리하여 화합물 H1-85 (5.5 g, 수율: 59%)를 얻었다.In a flask, compound 2 (5.0 g, 15.2 mmol), di([1,1'-biphenyl]-4-yl)amine (4.9 g, 15.2 mmol), Pd(OAc) 2 (0.2 g, 0.8 mmol), P(t-Bu) 3 (0.8 mL, 1.5 mmol), NaOt-Bu (2.9 g, 30.4 mmol) and 76 mL of xylene were added, and the mixture was stirred at 160° C. for 5 hours. After the reaction was completed, it was cooled to room temperature, and the precipitated solid was washed with distilled water and methanol. After separation by column chromatography, compound H1-85 (5.5 g, yield: 59%) was obtained.
[합성예 7] 화합물 H1-51의 제조[Synthesis Example 7] Preparation of compound H1-51
플라스크에 화합물 2 (4 g, 12 mmol), 비스(비페닐-4-일)[4-(4,4,5,5-테트라메틸-[1,3,2]-디옥사보로란-2-일)페닐]아민 (6.8 g, 13 mmol), Pd(OAc)2 (0.3 g, 1 mmol), S-Phos (0.9 g, 2 mmol), Cs2CO3 (11.5 g, 35 mmol), o-자일렌 60mL, EtOH 15 mL 및 증류수 15 mL를 넣고, 150℃에서 3시간 동안 환류교반하였다. 반응이 완료된 후, 상온으로 냉각하고 증류수로 씻어준 후 에틸 아세테이트로 유기층을 추출하고, 마그네슘 설페이트로 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 H1-51 (2.2 g, 수율: 27%)을 얻었다.In a flask, compound 2 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane- 2-yl)phenyl]amine (6.8 g, 13 mmol), Pd(OAc) 2 (0.3 g, 1 mmol), S-Phos (0.9 g, 2 mmol), Cs 2 CO 3 (11.5 g, 35 mmol) , o-xylene 60mL, EtOH 15mL and distilled water 15mL were put, and the mixture was stirred under reflux at 150℃ for 3 hours. After completion of the reaction, the reaction was cooled to room temperature, washed with distilled water, the organic layer was extracted with ethyl acetate, the residual moisture was removed with magnesium sulfate, dried, and separated by column chromatography for compound H1-51 (2.2 g, yield: 27 %) was obtained.
[합성예 8] 화합물 H1-68의 제조[Synthesis Example 8] Preparation of compound H1-68
플라스크에 화합물 7 (4.8 g, 11.34 mmol), N-(4-브로모페닐)-N-페닐-[1,1'-비페닐]-4-아민 (5 g, 12.47 mmol), Pd(PPh3)4 (0.4 g, 0.34 mmol), Na2CO3 (3.0 g, 28.35 mmol), 톨루엔 57 mL, 에탄올 14 mL 및 증류수 14 mL를 넣고, 120℃에서 4시간 동안 교반하였다. 반응이 완료된 후, 혼합물을 메탄올에 적가하고 생성된 고체를 여과하였다. 생성된 고체는 컬럼 크로마토그래피로 정제하여 화합물 H1-68 (1.4 g, 수율: 20.0%)를 얻었다.In a flask was placed compound 7 (4.8 g, 11.34 mmol), N-(4-bromophenyl)-N-phenyl-[1,1′-biphenyl]-4-amine (5 g, 12.47 mmol), Pd(PPh) 3 ) 4 (0.4 g, 0.34 mmol), Na 2 CO 3 (3.0 g, 28.35 mmol), toluene 57 mL, ethanol 14 mL and distilled water 14 mL were added, and the mixture was stirred at 120° C. for 4 hours. After the reaction was completed, the mixture was added dropwise to methanol and the resulting solid was filtered off. The resulting solid was purified by column chromatography to obtain compound H1-68 (1.4 g, yield: 20.0%).
[합성예 9] 화합물 H1-15의 제조[Synthesis Example 9] Preparation of compound H1-15
1) 화합물 8의 합성1) Synthesis of compound 8
플라스크에 화합물 2 (10.0 g, 30.3 mmol), [1,1'-비페닐]-3-아민 (6.7 g, 39.4 mmol), Pd(OAc)2 (0.34 g, 1.5 mmol), P(t-Bu)3 (1.5 mL, 3.03 mmol), NaOt-Bu (5.8 g, 60.6 mmol) 및 자일렌 150 mL를 넣고, 160℃에서 6 시간 동안 교반하였다. 반응이 완료된 후, 증류수로 씻어주고 에틸 아세테이트로 유기층을 추출하고 마그네슘 설페이트로 건조시킨 후 회전 증발기로 용매를 제거한 후, 컬럼 크로마토그래피로 분리하여 화합물 8 (10.8 g, 수율: 36%)을 얻었다.In a flask, put compound 2 (10.0 g, 30.3 mmol), [1,1'-biphenyl]-3-amine (6.7 g, 39.4 mmol), Pd(OAc) 2 (0.34 g, 1.5 mmol), P(t- Bu) 3 (1.5 mL, 3.03 mmol), NaOt-Bu (5.8 g, 60.6 mmol) and 150 mL of xylene were added, and the mixture was stirred at 160° C. for 6 hours. After the reaction was completed, the reaction was washed with distilled water, the organic layer was extracted with ethyl acetate, dried over magnesium sulfate, the solvent was removed by a rotary evaporator, and the mixture was separated by column chromatography to obtain compound 8 (10.8 g, yield: 36%).
2) 화합물 H1-15의 합성2) Synthesis of compound H1-15
플라스크에 화합물 8 (5.0 g, 10.8 mmol), 3-브로모 디벤조푸란 (3.2 g, 12.9 mmol), Pd2(dba)3 (0.5 g, 0.54 mmol), S-Phos (0.45 g, 1.08 mmol), NaOt-Bu (2.0 g, 21.6 mmol) 및 o-자일렌 60 mL를 넣고, 160℃에서 6시간 동안 교반하였다. 반응이 완료된 후, 상온으로 냉각하고 에틸 아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고, 컬럼 크로마토그래피로 분리하여 화합물 H1-15 (1.45 g, 수율: 21%)를 얻었다.Compound 8 (5.0 g, 10.8 mmol), 3-bromo dibenzofuran (3.2 g, 12.9 mmol), Pd 2 (dba) 3 (0.5 g, 0.54 mmol), S-Phos (0.45 g, 1.08 mmol) in a flask ), NaOt-Bu (2.0 g, 21.6 mmol) and o-xylene (60 mL) were added, and the mixture was stirred at 160°C for 6 hours. After the reaction was completed, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound H1-15 (1.45 g, yield: 21%). .
[합성예 10] 화합물 C-2 의 제조[Synthesis Example 10] Preparation of compound C-2
11-클로로벤조[b]나프토[2,3-d]티오펜 (3.6 g, 13.4 mmol), 2,4-디페닐-6-(3-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)페닐)-1,3,5-트리아진 (6.4 g, 14.77 mmol), Pd2(dba)3 (613 mg, 0.67 mmol), 2-디사이클로헥실포스피노-2',6'-디메톡시비페닐(S-Phos) (550 mg, 1.34 mmol) 및 K3PO4 (7.1 g, 33.5 mmol)에 o-자일렌 70 mL를 투입한 후 4시간 동안 환류교반하였다. 반응 종결 후, 혼합물을 실온으로 냉각한 뒤 실리카겔로 여과하였다. 유기층을 감압증류한 후 o-자일렌으로 재결정하여 화합물 C-2 (3.0 g, 수율: 41.3%)를 얻었다.11-Chlorobenzo [b] naphtho [2,3-d] thiophene (3.6 g, 13.4 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (6.4 g, 14.77 mmol), Pd 2 (dba) 3 (613 mg, 0.67 mmol), 2- 70 mL of o-xylene was added to dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (550 mg, 1.34 mmol) and K 3 PO 4 (7.1 g, 33.5 mmol) After that, the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through silica gel. The organic layer was distilled under reduced pressure and recrystallized from o-xylene to obtain compound C-2 (3.0 g, yield: 41.3%).
[합성예 11] 화합물 C-57 의 제조[Synthesis Example 11] Preparation of compound C-57
11-클로로벤조[b]나프토[2,3-d]푸란 (1.4 g, 5.5 mmol), 2,4-디페닐-6-(3-(4,4,5,5-테트라메틸-1,3,2-디옥사보롤란-2-일)페닐)-1,3,5-트리아진 (2.7 g, 6.1 mmol), Pd2(dba)3 (252 mg, 0.275 mmol), S-Phos (225 mg, 0.55 mmol) 및 K3PO4 (2.9 g, 13.75 mmol)에 o-자일렌 30 mL를 투입한 후 4시간 동안 환류교반하였다. 반응 종결 후, 혼합물을 실온으로 냉각한 뒤 실리카겔로 여과하였다. 유기층을 감압증류한 후 o-자일렌으로 재결정하여 화합물 C-57 (0.9 g, 수율: 30%)를 얻었다.11-Chlorobenzo [b] naphtho [2,3-d] furan (1.4 g, 5.5 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1) ,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (2.7 g, 6.1 mmol), Pd 2 (dba) 3 (252 mg, 0.275 mmol), S-Phos (225 mg, 0.55 mmol) and K 3 PO 4 (2.9 g, 13.75 mmol) was added with 30 mL of o-xylene, followed by stirring under reflux for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through silica gel. The organic layer was distilled under reduced pressure and recrystallized from o-xylene to obtain compound C-57 (0.9 g, yield: 30%).
[소자 실시예 1 및 2] 호스트로서 본 발명에 따른 화합물을 증착한 적색 발광 OLED의 제조[Device Examples 1 and 2] Preparation of a red light-emitting OLED in which a compound according to the present invention is deposited as a host
본 발명에 따른 OLED를 제조하였다. 우선, OLED 용 글래스 (지오마텍사 제조) 기판 상의 투명 전극 ITO 박막(10Ω/□)을 아세톤 및 이소프로필알코올을 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로필알코올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO 기판을 장착한 후, 진공 증착 장비 내의 셀에 표 3의 화합물 HI-1을 넣고, 또 다른 셀에는 표 3의 화합물 HT-1을 넣은 후, 두 물질을 다른 속도로 증발시켜 화합물 HI-1과 화합물 HT-1의 합계량에 대해 화합물 HI-1을 3 중량%의 양으로 10 nm 두께로 도핑하여 정공 주입층을 증착하였다. 이어서, 제1 정공 전달층으로 화합물 HT-1을 상기 정공 주입층 위에 80 nm 두께로 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 화합물 HT-2를 넣고, 셀에 전류를 인가하여 증발시켜 제1 정공 전달층 위에 60 nm 두께의 제2 정공 전달층을 증착하였다. 정공 주입층과 정공 전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 셀에 호스트로서 하기 표 1의 화합물을 넣고, 또 다른 셀에는 도판트로서 화합물 D-39를 넣은 후, 두 물질을 다른 속도로 증발시켜 호스트와 도판트의 합계량에 대해 도판트를 3 중량%의 양으로 도핑함으로써 상기 제2 정공 전달층 위에 40 nm 두께의 발광층을 증착하였다. 이어서, 또 다른 셀 두 군데 각각에 화합물 ETL-1과 화합물 EIL-1을 1:1의 속도로 증발시켜 발광층 위에 35 nm 두께의 전자 전달층을 증착하였다. 이어서, 전자 주입층으로 화합물 EIL-1을 상기 전자 전달층 위에 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 캐소드를 상기 전자 주입층 위에 80 nm의 두께로 증착하여 OLED를 제조하였다.An OLED according to the present invention was prepared. First, a transparent electrode ITO thin film (10Ω/□) on a glass (Giomatec) substrate for OLED was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropyl alcohol and stored for use. Next, after mounting the ITO substrate in the substrate holder of the vacuum deposition equipment, put the compound HI-1 of Table 3 into a cell in the vacuum deposition equipment, and put the compound HT-1 of Table 3 into another cell, and then the two materials A hole injection layer was deposited by doping the compound HI-1 to a thickness of 10 nm in an amount of 3 wt% based on the total amount of the compound HI-1 and the compound HT-1 by evaporation at different rates. Then, as a first hole transport layer, compound HT-1 was deposited on the hole injection layer to a thickness of 80 nm. Then, the compound HT-2 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. After putting the compound of Table 1 as a host in a cell in the vacuum deposition equipment, and putting compound D-39 as a dopant in another cell, the two materials were evaporated at different rates to give the dopant for the total amount of the host and the dopant. A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by doping in an amount of 3 wt%. Subsequently, compound ETL-1 and compound EIL-1 were evaporated at a rate of 1:1 in each of two other cells to deposit an electron transport layer with a thickness of 35 nm on the emission layer. Then, after depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED. .
[비교예 1] 호스트로서 종래의 화합물을 증착한 적색 발광 OLED의 제조[Comparative Example 1] Preparation of a red light-emitting OLED in which a conventional compound is deposited as a host
발광층의 호스트로서 하기 표 3의 화합물 A를 사용한 것 외에는 소자 실시예 1 및 2와 동일한 방법으로 OLED를 제조하였다.OLEDs were manufactured in the same manner as in Device Examples 1 and 2, except that Compound A of Table 3 was used as a host of the emission layer.
이상과 같이 제조된 소자 실시예 1 및 2와 비교예 1의 유기 전계 발광 소자의 1,000 nit 휘도 기준의 구동전압, 발광효율, 전력효율 및 발광색을 하기 표 1에 나타내었다.The driving voltage, luminous efficiency, power efficiency and luminous color of the organic electroluminescent devices of Examples 1 and 2 and Comparative Example 1 prepared as described above based on 1,000 nit luminance are shown in Table 1 below.
[표 1][Table 1]
상기 표 1로부터 본원에 따른 유기 전계 발광 화합물을 호스트로 포함하는 유기 전계 발광 소자가 비교예 1의 유기 전계 발광 소자와 동등 수준의 발광효율을 나타내면서 비교예 1에 비해 우수한 구동전압 및 전력효율 특성을 제공함을 확인할 수 있다. 본원에 따른 호스트 재료를 포함하는 유기 전계 발광 소자는 수명 특성에 있어서도 이점이 있을 수 있다.From Table 1 above, the organic electroluminescent device including the organic electroluminescent compound according to the present application as a host exhibited luminous efficiency equivalent to that of the organic electroluminescent device of Comparative Example 1, and excellent driving voltage and power efficiency characteristics compared to Comparative Example 1. You can verify that it is provided. An organic electroluminescent device including a host material according to the present disclosure may have advantages in terms of lifetime characteristics.
본원에 따른 화학식 2'로 표시되는 유기 전계 발광 화합물 및 화학식 2"로 표시되는 유기 전계 발광 화합물에서, 모핵의 LUMO 에너지 준위, HOMO 에너지 준위 및 삼중항 에너지를 각각 측정하여 하기 표 1-1에 나타내었다.In the organic electroluminescent compound represented by Formula 2' and the organic electroluminescent compound represented by Formula 2" according to the present application, the LUMO energy level, HOMO energy level, and triplet energy of the parent nucleus were respectively measured and shown in Table 1-1 below. it was
[표 1-1][Table 1-1]
* 가우시안 사의 양자 화학 계산 프로그램인 Gaussian 16으로 혼성 밀도 함수이론 (hybrid DFT: Density Functional Theory)인 B3LYP 와 6-31G(d)의 바탕 집합을 적용하여 구조를 최적화하였으며, TD-DFT (time dependent DFT)를 이용하여 삼중항 상태를 계산하였다.* The structure was optimized by applying the background sets of B3LYP and 6-31G(d), which are hybrid DFT: Density Functional Theory, with Gaussian 16, Gaussian's quantum chemistry calculation program, and TD-DFT (time dependent DFT) ) was used to calculate the triplet state.
상기 표 1-1을 참조하면, 본 발명에 따른 화학식 2"로 표시되는 유기 전계 발광 화합물 (R20 또는 R25에 치환기를 도입)의 모핵이 소자 실시예 1 및 2에서 사용된 화학식 2'로 표시되는 유기 전계 발광 화합물 C-2 및 C-57의 모핵과 비슷한 에너지 레벨을 갖는 것을 확인할 수 있다. 이를 통하여 화학식 2"의 유기 전계 발광 화합물을 호스트 재료로 사용할 경우에도 상기 소자 실시예 1 및 2와 유사한 소자 특성을 가질 것으로 예상할 수 있다.Referring to Table 1-1, the parent nucleus of the organic electroluminescent compound (introducing a substituent to R 20 or R 25 ) represented by Formula 2" according to the present invention is represented by Formula 2' used in Device Examples 1 and 2 It can be seen that the displayed organic electroluminescent compounds C-2 and C-57 have similar energy levels to the parent nuclei. Through this, even when the organic electroluminescent compound of Formula 2" is used as a host material, the device Examples 1 and 2 It can be expected to have similar device characteristics to
[소자 실시예 3 내지 5] 호스트로서 본 발명에 따른 복수 종의 호스트 재료를 증착한 적색 발광 OLED의 제조[Device Examples 3 to 5] Preparation of a red light emitting OLED in which a plurality of types of host materials according to the present invention are deposited as a host
발광층을 증착함에 있어서 셀 두 군데에 호스트로서 하기 표 2에 기재된 각각의 제1 호스트 화합물 및 제2 호스트 화합물을 넣고, 또 다른 셀에는 화합물 D-39를 넣은 후, 두 호스트 물질을 1:1의 속도로 증발시키고 동시에 도판트 물질을 다른 속도로 증발시켜 호스트와 도판트의 합계량에 대해 도판트를 3 중량%의 양으로 도핑함으로써 증착한 것 외에는 소자 실시예 1 및 2와 동일한 방법으로 OLED를 제조하였다.In depositing the light emitting layer, each of the first host compound and the second host compound described in Table 2 below as hosts were put in two cells, and after putting compound D-39 in another cell, the two host materials were mixed in a 1:1 ratio. An OLED was manufactured in the same manner as in Device Examples 1 and 2, except that deposition was carried out by evaporating at a rate and simultaneously evaporating the dopant material at different rates, thereby doping the dopant in an amount of 3 wt% with respect to the total amount of the host and dopant. did
이상과 같이 제조된 소자 실시예 3 내지 5의 유기 전계 발광 소자의 1,000 nit 휘도 기준의 구동전압, 발광효율 및 발광색을 하기 표 2에 나타내었다.Table 2 below shows the driving voltage, luminous efficiency, and emission color based on 1,000 nit luminance of the organic electroluminescent devices of Device Examples 3 to 5 prepared as described above.
[표 2][Table 2]
앞서, 소자 실시예 1 및 2에서 본원의 화학식 2' 또는 화학식 2"로 표시되는 유기 전계 발광 화합물을 단독 호스트로 사용한 경우, 우수한 발광효율, 구동전압 및 전력효율 특성을 갖는 OLED를 제공함을 확인한 바 있다. 이에 더하여, 상기 표 2로부터 본원에 따른 복수 종의 호스트 재료를 호스트로 포함하는 유기 전계 발광 소자는 본원의 화학식 2' 또는 화학식 2"로 표시되는 유기 전계 발광 화합물을 단독 호스트로 사용한 경우보다 더욱 우수한 구동전압, 발광효율 및/또는 전력효율 특성을 제공함을 확인할 수 있다. 본원에 따른 복수 종의 호스트 재료를 포함하는 유기 전계 발광 소자는 수명 특성에 있어서도 이점이 있을 수 있다.Previously, when the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present application was used as a single host in Device Examples 1 and 2, it was confirmed that an OLED having excellent luminous efficiency, driving voltage and power efficiency characteristics was provided. In addition, from Table 2 above, the organic electroluminescent device including a plurality of types of host materials according to the present application as a host is higher than when the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present application is used as a single host. It can be confirmed that more excellent driving voltage, luminous efficiency and/or power efficiency characteristics are provided. The organic electroluminescent device including a plurality of types of host materials according to the present disclosure may have advantages in lifespan characteristics.
이론으로써 제한하는 것은 아니나, 본원 화학식 2의 화합물을 제2 호스트로 사용함으로써 발광층이 전자 우세 시스템이 되도록 하였고, 아민계 화합물인 본원 화학식 1의 화합물을 제1 호스트로 사용하여 정공을 많이 제공함으로써 엑시톤이 풍부하게 제공되도록 하였다. 또한, 이론으로써 제한하는 것은 아니나, 제1 호스트의 높은 HOMO 에너지 레벨로 인해 정공 전달층/발광층 간 HOMO 배리어를 낮출 수 있었다. 결과적으로 낮은 구동전압, 높은 전력효율 및 장수명의 특성을 얻을 수 있다.Although not limited by theory, the light emitting layer is made into an electron-dominant system by using the compound of Formula 2 as the second host, and the compound of Formula 1, which is an amine compound, is used as the first host to provide a large number of holes to exciton to be provided in abundance. In addition, without being limited by theory, it was possible to lower the HOMO barrier between the hole transport layer/emission layer due to the high HOMO energy level of the first host. As a result, characteristics of low driving voltage, high power efficiency, and long life can be obtained.
상기 소자 실시예 1 내지 5 및 비교예 1에 사용된 화합물은 하기 표 3에 나타내었다.The compounds used in Device Examples 1 to 5 and Comparative Example 1 are shown in Table 3 below.
[표 3][Table 3]
[소자 실시예 6] 전자 전달층으로서 본 발명에 따른 화합물을 증착한 청색 발광 OLED의 제조[Device Example 6] Preparation of blue light emitting OLED in which the compound according to the present invention is deposited as an electron transport layer
본 발명에 따르는 OLED를 제조하였다. 우선, OLED용 글래스 (지오마텍사 제조) 기판 상의 투명 전극 ITO 박막(10Ω/□)을 아세톤 및 이소프로필알코올을 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로필알코올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO 기판을 장착한 후, 진공 증착 장비 내의 셀에 제1정공 주입 화합물로서 표5에 기재된 화합물HI-1을 넣고, 또 다른 셀에는 표 5에 기재된 화합물 HT-1을 넣은 후, 두 물질을 다른 속도로 증발시켜 화합물HI-1과 화합물 HT-1의 합계량에 대해 화합물HI-1을 3 중량%의 양으로 10 nm 두께로 도핑하여 정공 주입층을 증착하였다. 이어서, 제1 정공 전달층으로 화합물 HT-1을 상기 정공 주입층 위에 80 nm 두께로 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 화합물 HT-3를 넣고, 셀에 전류를 인가하여 증발시켜 상기 제1 정공 전달층 위에 5 nm 두께의 제2 정공 전달층을 증착하였다. 정공 주입층과 정공 전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. OLEDs according to the invention were prepared. First, a transparent electrode ITO thin film (10Ω/□) on a glass for OLED (Giomatec) substrate was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropyl alcohol and stored for use. Next, after mounting the ITO substrate on the substrate holder of the vacuum deposition equipment, the compound HI-1 described in Table 5 as the first hole injection compound was put into the cell in the vacuum deposition equipment, and the compound HT- After adding 1 , the two substances were evaporated at different rates to give compound HI-1 and A hole injection layer was deposited by doping the compound HI-1 to a thickness of 10 nm in an amount of 3 wt% with respect to the total amount of the compound HT-1 . Then, as a first hole transport layer, compound HT-1 was deposited on the hole injection layer to a thickness of 80 nm. Then, the compound HT-3 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying a current to deposit a second hole transport layer having a thickness of 5 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows.
진공 증착 장비 내의 셀 두 군데에 호스트로서 하기 표 5에 기재된 BH 호스트 화합물을 넣고, 또 다른 셀에는 도판트로서 화합물 BD을 넣은 후, 두 호스트 물질을 1:1의 속도로 증발시키고 동시에 도판트 물질을 다른 속도로 증발시켜 호스트와 도판트의 합계량에 대해 도판트를 3중량%의 양으로 도핑함으로써 상기 정공 전달층 위에 20 nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 버퍼층으로서 화합물 BF를 5 nm 두께로 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로서 표5의 화합물 C-2와 화합물 EIL-1을 50:50 중량비로30 nm 두께로 증착하였다. 이어서 전자 주입층으로 화합물 EIL-1을 상기 전자 전달층 위에 2 nm두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 상기 전자 주입층 위에 80 nm의 두께로 증착하여 OLED를 제조하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.After putting the BH host compound shown in Table 5 below as a host in two cells in the vacuum deposition equipment, and putting compound BD as a dopant in another cell, the two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously A light emitting layer with a thickness of 20 nm was deposited on the hole transport layer by evaporating at different rates and doping the dopant in an amount of 3 wt% with respect to the total amount of the host and the dopant. Subsequently, compound BF was deposited to a thickness of 5 nm as an electron buffer layer on the light emitting layer. Then, as an electron transport layer on the light emitting layer Compound C-2 and compound EIL-1 of Table 5 were deposited to a thickness of 30 nm in a 50:50 weight ratio. Then, after depositing the compound EIL-1 as an electron injection layer to a thickness of 2 nm on the electron transport layer, an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED. For each material, each compound was purified by vacuum sublimation under 10 -6 torr.
[비교예 2] 전자 전달층으로서 종래의 화합물을 증착한 청색 발광 OLED의 제조[Comparative Example 2] Manufacture of blue light emitting OLED in which a conventional compound is deposited as an electron transport layer
전자 전달층으로서 하기 표 5에 기재된 화합물 C-2 대신에 화합물 A를 사용한 것 외에는 소자 실시예 6 과 동일한 방법으로 OLED를 제조하였다. An OLED was manufactured in the same manner as in Device Example 6 except that Compound A was used instead of Compound C-2 shown in Table 5 as an electron transport layer.
이상과 같이 제조된 소자 실시예 6 및 비교예 2의 유기 전계 발광 소자의 1,000 nit 휘도 기준의 구동 전압, 발광효율, 발광색 및 외부 양자효율을 하기 표 4에 나타내었다.The driving voltage, luminous efficiency, luminous color and external quantum efficiency based on 1,000 nit luminance of the organic electroluminescent device of Example 6 and Comparative Example 2 prepared as described above are shown in Table 4 below.
[표 4][Table 4]
상기 표 4로부터 본원에 따른 화합물을 전자 전달층으로 포함하는 유기 전계 발광 소자는 종래의 화합물을 전자 전달층으로 포함하는 비교예 2의 유기 전계 발광 소자에 비하여 우수한 구동전압, 발광효율 및/또는 외부 양자효율 특성을 제공함을 확인할 수 있다.From Table 4, the organic electroluminescent device including the compound according to the present application as an electron transport layer has superior driving voltage, luminous efficiency and/or external compared to the organic electroluminescent device of Comparative Example 2 including the conventional compound as an electron transport layer. It can be confirmed that quantum efficiency characteristics are provided.
상기 소자 실시예 6 및 비교예 2에 사용된 화합물은 하기 표 5에 나타내었다.The compounds used in Device Example 6 and Comparative Example 2 are shown in Table 5 below.
[표 5][Table 5]
Claims (14)
[화학식 2']
상기 화학식 2'에서,
HAr은 각각 독립적으로 치환 또는 비치환된 트리아지닐, 치환 또는 비치환된 피리딜, 치환 또는 비치환된 피리미디닐, 치환 또는 비치환된 퀴나졸리닐, 치환 또는 비치환된 벤조퀴나졸리닐, 치환 또는 비치환된 퀴녹살리닐, 치환 또는 비치환된 벤조퀴녹살리닐, 치환 또는 비치환된 벤조푸로피리미디닐, 또는 치환 또는 비치환된 벤조티에노피리미디닐이고;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;
[화학식 3] [화학식 4] [화학식 5]
상기 화학식 3 내지 5에서,
Y2는 O 또는 S이며;
R20 내지 R29은 수소 또는 중수소이고;
e는 1 또는 2이며, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있으며;
*는 L11와 연결되는 위치를 나타내고;
단, HAr이 치환된 트리아지닐인 경우, 트리아지닐의 치환기는 각각 독립적으로 중수소, 페닐, 나프틸, 비페닐, 터페닐, 페난트레닐, 트리페닐레닐, 디메틸플루오레닐, 플루오란테닐, 크라이세닐, 카바졸릴 및 이들의 조합으로부터 선택되고, 치환기가 2개인 경우 이들은 서로 같거나 상이하다.An organic electroluminescent compound represented by the following formula 2':
[Formula 2']
In Formula 2',
Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, or substituted or unsubstituted benzothienopyrimidinyl;
L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar 11 is each independently any one of Formulas 3 to 5;
[Formula 3] [Formula 4] [Formula 5]
In Formulas 3 to 5,
Y 2 is O or S;
R 20 to R 29 are hydrogen or deuterium;
e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
* indicates a position connected to L 11 ;
However, when HAr is substituted triazinyl, the substituents of triazinyl are each independently deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, fluoranthenyl, cry senyl, carbazolyl, and combinations thereof, and when there are two substituents, they are the same as or different from each other.
[화학식 2"]
상기 화학식 2"에서,
HAr은 각각 독립적으로 치환 또는 비치환된 트리아지닐, 치환 또는 비치환된 퀴나졸리닐, 치환 또는 비치환된 벤조퀴나졸리닐, 치환 또는 비치환된 퀴녹살리닐, 치환 또는 비치환된 벤조퀴녹살리닐, 치환 또는 비치환된 벤조푸로피리미디닐, 또는 치환 또는 비치환된 벤조티에노피리미디닐이고;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;
[화학식 3] [화학식 4] [화학식 5]
상기 화학식 3 내지 5에서,
Y2는 O 또는 S이며;
R21 내지 R24 및 R26 내지 R29은 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;
R20 및 R25는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이며;
e는 1 또는 2이고, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있으며;
*는 L11와 연결되는 위치를 나타낸다.An organic electroluminescent compound represented by the following formula (2):
[Formula 2"]
In Formula 2",
Each HAr is independently substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl , a substituted or unsubstituted benzofuropyrimidinyl, or a substituted or unsubstituted benzothienopyrimidinyl;
L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar 11 is each independently any one of Formulas 3 to 5;
[Formula 3] [Formula 4] [Formula 5]
In Formulas 3 to 5,
Y 2 is O or S;
R 21 to R 24 and R 26 to R 29 are each independently hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R 20 and R 25 are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
* indicates a position connected to L 11 .
The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 2' is selected from the following compounds.
The organic electroluminescent compound according to claim 2, wherein the compound represented by Formula 2" is selected from the following compounds.
[화학식 1]
상기 화학식 1에서,
X1 및 Y1은 각각 독립적으로 -N=, -NR5-, -O- 또는 -S-이고, 단, X1 및 Y1 중 어느 하나는 -N=이고, X1 및 Y1 중 다른 하나는 -NR5-, -O- 또는 -S-이며;
R1은 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;
L1는 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;
R2 내지 R5은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 또는 -L3-N(Ar3)(Ar4)이거나; 인접한 치환기끼리 서로 연결되어 고리를 형성할 수 있으며;
a는 1이고, b 및 c는 각각 독립적으로 1 또는 2이며, d 는 1 내지 4의 정수이고, b 내지 d가 2 이상의 정수인 경우, 각각의 R2 내지 R4는 서로 동일하거나 상이할 수 있으며;
[화학식 2]
상기 화학식 2에서,
HAr은 각각 독립적으로 치환 또는 비치환된 질소 함유 (3-20원)헤테로아릴이고;
L11은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;
Ar11은 각각 독립적으로 하기 화학식 3 내지 5 중 어느 하나이고;
[화학식 3] [화학식 4] [화학식 5]
상기 화학식 3 내지 5에서,
Y2는 O 또는 S이며;
R20 내지 R29은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 (C1-C30)알킬디(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 또는 -L3-N(Ar3)(Ar4)이고;
e는 1 또는 2이며, e가 2인 경우, 각각의 (L11-HAr)은 서로 동일하거나 상이할 수 있고;
*는 L11와 연결되는 위치를 나타내고;
상기 화학식 1 및 3 내지 5에서,
L3은 각각 독립적으로 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (3-30원)헤테로아릴렌이며;
Ar3 및 Ar4는 각각 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C3-C30)의 지방족고리와 (C6-C30)의 방향족고리의 융합고리기, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이다.A plurality of host materials including at least one first host compound and at least one second host compound, wherein the first host compound is represented by Formula 1 below, and the second host compound is represented by Formula 2 below wherein a plurality of species of host material:
[Formula 1]
In Formula 1,
X 1 and Y 1 are each independently -N=, -NR 5 -, -O- or -S-, with the proviso that any one of X 1 and Y 1 is -N=, and the other of X 1 and Y 1 one is -NR 5 -, -O- or -S-;
R 1 is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
L 1 is a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar 1 and Ar 2 are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R 2 to R 5 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L 3 -N(Ar 3 )(Ar 4 ); adjacent substituents may be linked to each other to form a ring;
a is 1, b and c are each independently 1 or 2, d is an integer of 1 to 4, and when b to d are an integer of 2 or more, each R 2 to R 4 may be the same or different from each other, ;
[Formula 2]
In Formula 2,
each HAr is independently a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl;
L 11 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar 11 is each independently any one of Formulas 3 to 5;
[Formula 3] [Formula 4] [Formula 5]
In Formulas 3 to 5,
Y 2 is O or S;
R 20 to R 29 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring fused ring group, or -L 3 -N(Ar 3 )(Ar 4 );
e is 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other;
* indicates a position connected to L 11 ;
In Formulas 1 and 3 to 5,
L 3 is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar 3 and Ar 4 are each independently hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C3-C30) aliphatic ring; (C6-C30) is a fused ring group of an aromatic ring, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.
[화학식 1-1] [화학식 1-2]
[화학식 1-3] [화학식 1-4]
상기 화학식 1-1 내지 1-4에서,
R1 내지 R4, Ar1, Ar2, L1 및 a 내지 d는 제7항에서 정의된 것과 같다.The method according to claim 7, wherein Chemical Formula 1 is represented by one or more of the following Chemical Formulas 1-1 to 1-4, a plurality of host materials:
[Formula 1-1] [Formula 1-2]
[Formula 1-3] [Formula 1-4]
In Formulas 1-1 to 1-4,
R 1 to R 4 , Ar 1 , Ar 2 , L 1 and a to d are as defined in claim 7.
The plurality of host materials according to claim 7, wherein the compound represented by Formula 1 is at least one selected from the following compounds.
The plurality of host materials according to claim 7, wherein the compound represented by Formula 2 is at least one selected from the following compounds.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102021119077.0A DE102021119077A1 (en) | 2020-07-24 | 2021-07-22 | ORGANIC ELECTROLUMINESCENT COMPOUND, MULTIPLE HOST MATERIALS AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCENT DEVICE |
CN202110833828.5A CN113968847A (en) | 2020-07-24 | 2021-07-22 | Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same |
US17/384,108 US20220033414A1 (en) | 2020-07-24 | 2021-07-23 | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same |
JP2021121805A JP2022022206A (en) | 2020-07-24 | 2021-07-26 | Organic electroluminescent compound, plural host materials, and organic electroluminescent device using the same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200092465 | 2020-07-24 | ||
KR20200092465 | 2020-07-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20220013315A true KR20220013315A (en) | 2022-02-04 |
Family
ID=80268221
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020210082869A KR20220013315A (en) | 2020-07-24 | 2021-06-25 | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR20220013315A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102510819B1 (en) * | 2022-10-11 | 2023-03-16 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using the same, and an electronic device thereof |
WO2023200315A1 (en) * | 2022-04-15 | 2023-10-19 | 주식회사 엘지화학 | Novel compound and organic light-emitting device using same |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20120104067A (en) | 2011-03-11 | 2012-09-20 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
-
2021
- 2021-06-25 KR KR1020210082869A patent/KR20220013315A/en active Search and Examination
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20120104067A (en) | 2011-03-11 | 2012-09-20 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023200315A1 (en) * | 2022-04-15 | 2023-10-19 | 주식회사 엘지화학 | Novel compound and organic light-emitting device using same |
KR102510819B1 (en) * | 2022-10-11 | 2023-03-16 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using the same, and an electronic device thereof |
WO2024080655A1 (en) * | 2022-10-11 | 2024-04-18 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device having same |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102283849B1 (en) | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same | |
KR102306966B1 (en) | Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same | |
KR20200125080A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20210008812A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20210098399A (en) | Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same | |
KR20210082888A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20210054737A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20210109436A (en) | Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same | |
KR20220051794A (en) | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same | |
KR20220012180A (en) | A plurality of light-emitting materials, organic electroluminescent compound, and organic electroluminescent device comprising the same | |
KR20220051976A (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
KR20220055895A (en) | Organic electroluminescent device | |
KR20210120339A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20220013315A (en) | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same | |
KR20210116214A (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
KR20210082068A (en) | Organic electroluminescent compound, organic electroluminescent material comprising the same, and organic electroluminescent device | |
KR20210143521A (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
KR20200115148A (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
KR20210116819A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20210071602A (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
KR20220010427A (en) | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same | |
KR20210139134A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20210010310A (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
KR20220021651A (en) | Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same | |
KR20210070738A (en) | A plurality of host materials and organic electroluminescent device comprising the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination |