CN112739704B - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
- Publication number
- CN112739704B CN112739704B CN201980061411.2A CN201980061411A CN112739704B CN 112739704 B CN112739704 B CN 112739704B CN 201980061411 A CN201980061411 A CN 201980061411A CN 112739704 B CN112739704 B CN 112739704B
- Authority
- CN
- China
- Prior art keywords
- group
- light emitting
- compound
- chemical formula
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 88
- 239000000126 substance Substances 0.000 claims description 64
- -1 dibenzofuranyl Chemical group 0.000 claims description 52
- 239000011368 organic material Substances 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000004305 biphenyl Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 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 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000005428 anthryl 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 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 157
- 238000006243 chemical reaction Methods 0.000 description 52
- 239000000463 material Substances 0.000 description 43
- 238000002360 preparation method Methods 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 33
- 239000000243 solution Substances 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- 230000000903 blocking effect Effects 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- 230000032258 transport Effects 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000284 extract Substances 0.000 description 16
- 238000010898 silica gel chromatography Methods 0.000 description 15
- 229940125904 compound 1 Drugs 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- YBNDRTRLXPEWKQ-UHFFFAOYSA-N (4-chloro-2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1F YBNDRTRLXPEWKQ-UHFFFAOYSA-N 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- DXJHUCBRDBXOOA-UHFFFAOYSA-N 2,3-difluoro-1,4-diiodobenzene Chemical compound FC1=C(F)C(I)=CC=C1I DXJHUCBRDBXOOA-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- NZRRMTBNTSBIFH-UHFFFAOYSA-N (4-chloro-2-methoxyphenyl)boronic acid Chemical compound COC1=CC(Cl)=CC=C1B(O)O NZRRMTBNTSBIFH-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- PPUZKAPOPPRMFE-UHFFFAOYSA-N 1,5-dibromo-2,4-difluorobenzene Chemical compound FC1=CC(F)=C(Br)C=C1Br PPUZKAPOPPRMFE-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- VALXCIRMSIFPFN-UHFFFAOYSA-N 2,5-dibromobenzene-1,4-diol Chemical compound OC1=CC(Br)=C(O)C=C1Br VALXCIRMSIFPFN-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- CBVHWGKANITCQP-UHFFFAOYSA-N 3-fluorodibenzofuran Chemical compound C1=CC=C2C3=CC=C(F)C=C3OC2=C1 CBVHWGKANITCQP-UHFFFAOYSA-N 0.000 description 1
- CXOAKJLNBGFLEF-UHFFFAOYSA-N 3-fluorodibenzothiophene Chemical compound C1=CC=C2C3=CC=C(F)C=C3SC2=C1 CXOAKJLNBGFLEF-UHFFFAOYSA-N 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 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
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- JIGSWDKRFQWANT-UHFFFAOYSA-N 5-chloro-2-iodophenol Chemical compound OC1=CC(Cl)=CC=C1I JIGSWDKRFQWANT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([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
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 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 group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides novel compounds and organic light emitting devices comprising the same.
Description
Technical Field
The present application claims priority or benefit of korean patent application No. 10-2018-0155293, which was filed on the date 5 of 12 in 2018, and korean patent application No. 10-2019-0139529, which was filed on the date 4 of 11 in 2019, which disclosures are incorporated herein by reference in their entireties.
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has characteristics such as a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage, and response speed, and thus many researches have been conducted.
The organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. In order to improve efficiency and stability of the organic light emitting device, the organic material layer often has a multi-layered structure including different materials, for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, electrons are injected into the organic material layer from the cathode, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to the ground state again.
There is a continuing need to develop new materials for organic materials used in organic light emitting devices as described above.
[ Prior Art literature ]
[ patent literature ]
(patent document 1) Korean unexamined patent publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
It is an object of the present invention to provide a novel organic light emitting material and an organic light emitting device comprising the same.
Technical proposal
In one aspect of the present invention, there is provided a compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein, in the chemical formula 1,
a is a benzene ring condensed with two adjacent rings,
X 1 and X 2 Each independently is O or S,
Y 1 to Y 3 Each independently is N or CH, provided that Y 1 To Y 3 At least one of which is N,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 1 to R 3 Each independently is hydrogen; deuterium; halogen; cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 4 and R is 5 Each independently is hydrogen; deuterium; halogen; cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising at least one selected from N, O and S 2-60 A heteroaryl group, which is a group,
a and b are each independently integers from 0 to 4,
c is an integer of 0 to 2
d and e are each independently integers from 0 to 3.
In another aspect of the present invention, there is provided an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound represented by chemical formula 1.
Advantageous effects
The compound represented by chemical formula 1 described above may be used as a material of an organic material layer of an organic light emitting device, and may improve efficiency, achieve a low driving voltage, and/or improve lifetime characteristics in the organic light emitting device. In particular, the compound represented by chemical formula 1 may be used as a hole injecting material, a hole transporting material, a hole injecting and transporting material, an electron blocking material, a light emitting material, a hole blocking material, an electron transporting material, or an electron injecting material.
Drawings
Fig. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 3, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 4.
Detailed Description
Hereinafter, embodiments of the present invention will be described in more detail to aid understanding of the present invention.
An embodiment of the present invention provides a compound represented by chemical formula 1.
As used herein, a symbolMeaning a bond to another substituent.
As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio; arylthio; an alkylsulfonyl group; arylsulfonyl; a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a heterocyclic group containing at least one of N, O and S atoms, or a substituent which is unsubstituted or linked via two or more substituents among the substituents exemplified above. For example, a "substituent in which two or more substituents are linked" may be a biphenyl group. That is, biphenyl may also be aryl, and may be interpreted as a substituent to which two phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40.
Specifically, the carbonyl group may be a group having the following structural formula, but is not limited thereto.
In the present specification, the ester group may have a structure in which oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a group having the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a group having the following structural formula, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, and phenylboron group, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.
In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has a carbon number of 1 to 20. According to another embodiment, the alkyl group has a carbon number of 1 to 10. According to another embodiment, the alkyl group has a carbon number of 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be straight or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has a carbon number of 2 to 10. According to yet another embodiment, the alkenyl group has a carbon number of 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthalen-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the cycloalkyl group has a carbon number of 3 to 30. According to another embodiment, the cycloalkyl group has a number of carbon atoms of 3 to 20. According to yet another embodiment, the cycloalkyl group has a number of carbon atoms of 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has a carbon number of 6 to 30. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, an aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,A radical, a fluorenyl radical, etc., but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and two substituents may be linked to each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be formed Etc. However, the structure is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of heterocyclyl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, and i ∈ ->Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In this specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group are the same as those of the foregoing examples of the aryl groups. In this specification, the alkyl groups in the aralkyl group, alkylaryl group, and alkylamino group are the same as those of the aforementioned examples of the alkyl group. In this specification, the heteroaryl group in the heteroarylamine group may be used as described for the aforementioned heterocyclic group. In this specification, alkenyl groups in aralkenyl groups are the same as the aforementioned examples of alkenyl groups. In the present specification, the foregoing description of aryl groups may be applied, except that arylene groups are divalent groups. In the present specification, the foregoing description of the heterocyclic group may be applied, except that the heteroarylene group is a divalent group. In the present specification, the foregoing description of aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In this specification, the foregoing description of the heterocyclic group may be applied, except that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.
In chemical formula 1, chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-6 according to the condensed position of the benzene ring a:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
Wherein, in chemical formulas 1-1 to 1-6,
X 1 、X 2 、Y 1 to Y 3 、Ar 1 、Ar 2 、R 1 To R 5 And a to e are the same as defined in chemical formula 1.
At this time, a represents R 1 And when a is 2 or more, two or more R 1 May be the same or different from each other. The description of b to e can be understood with reference to the description of a and the structure of chemical formula 1.
Preferably Y 1 To Y 3 All may be N.
Preferably Ar 1 And Ar is a group 2 May each independently be a substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 6-20 Heteroaryl groups.
More preferably Ar 1 And Ar is a group 2 May each independently be phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, or phenyl substituted with 5 deuterium.
Preferably Ar 1 And Ar is a group 2 At least one of which may be substituted or unsubstituted C 6-60 Aryl groups.
More preferably Ar 1 And Ar is a group 2 At least one of which may be substituted or unsubstituted C 6-20 Aryl groups.
Most preferably Ar 1 And Ar is a group 2 At least one of which may be phenyl or phenyl substituted with 5 deuterium.
R 3 Is a substituent on benzene ring A.
Preferably, R 1 To R 3 May each independently be hydrogen; deuterium; substituted or unsubstituted C 1-20 An alkyl group; substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 6-20 Heteroaryl groups.
More preferably, R 1 To R 3 May each independently be hydrogen, deuterium, or phenyl.
Preferably, R 4 And R is 5 May each independently be hydrogen; substituted or unsubstituted C 1-20 An alkyl group; substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 6-20 Heteroaryl groups.
More preferably, R 4 And R is 5 May each independently be hydrogen or deuterium.
Representative examples of the compound represented by chemical formula 1 are as follows:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
。
the compound represented by chemical formula 1 may be prepared, for example, according to the preparation methods as shown in the following reaction schemes 1 and 2, and the other remaining compounds may be prepared in a similar manner.
Reaction scheme 1
Reaction scheme 2
In schemes 1 and 2, X 1 、X 2 、A、Y 1 To Y 3 、Ar 1 、Ar 2 And R is 1 To R 3 Z is the same as defined in chemical formula 1 1 And Z 2 Is halogen, and more preferably Z 1 And Z 2 Bromine or chlorine.
Reaction scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction may be varied as known in the art. Furthermore, reaction scheme 2 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the amine substitution reaction may be varied as known in the art. The above preparation method may be further presented in the preparation examples described below.
Another embodiment of the present invention provides an organic light emitting device including the above compound represented by chemical formula 1. As an example, there is provided an organic light emitting device, including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound represented by chemical formula 1.
The organic material layer of the organic light emitting device of the present invention may have a single layer structure, or it may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as the organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic material layers.
Further, the organic material layer may include a light emitting layer, a hole transporting layer, a hole injecting layer, or a layer for simultaneously performing hole transport and hole injection, wherein the light emitting layer, the hole transporting layer, the hole injecting layer, or the layer for simultaneously performing hole transport and hole injection may include a compound represented by chemical formula 1.
Further, the organic material layer may include a light emitting layer, wherein the light emitting layer includes a compound represented by chemical formula 1. In particular, the compound according to the present invention may be used as a host of the light emitting layer.
Further, the organic material layer may include a light emitting layer, an electron transporting layer, an electron injecting layer, and a layer for simultaneously performing electron transport and electron injection, wherein the light emitting layer, the electron transporting layer, the electron injecting layer, and the layer for simultaneously performing electron transport and electron injection may include a compound represented by chemical formula 1.
Further, the organic material layer includes a light emitting layer, an electron blocking layer, and an electron transporting layer, wherein the light emitting layer may include a compound represented by chemical formula 1.
Further, the organic light emitting device according to the present invention may be a normal organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present disclosure may be an inverted organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to one embodiment of the present disclosure is shown in fig. 1 and 2.
Fig. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in the light emitting layer.
Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 3, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 4. In such a structure, the compound represented by chemical formula 1 may be included in one or more of a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that one or more of the organic material layers include a compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by: a metal, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method (e.g., a sputtering method or an electron beam evaporation method) to form an anode, an organic material layer including a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer is formed on the anode, and then a material that can function as a cathode is deposited on the organic material layer. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, in manufacturing an organic light emitting device, the compound represented by chemical formula 1 may be formed into an organic material layer by a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, knife coating, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (international publication WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
As the anode material, a material having a large work function is generally preferably used,so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO, al or SnO 2 Sb; conductive polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ](PEDOT), polypyrrole, and polyaniline; etc., but is not limited thereto.
As the cathode material, it is generally preferable to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials, e.g. LiF/Al or LiO 2 Al; etc., but is not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound of: it has a capability of transporting holes, and thus has an effect of injecting holes in an anode and an excellent effect of injecting holes into a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and is excellent in a capability of forming a thin film. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazabenzophenanthrene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and polythiophene-based conductive polymer, and the like, but are not limited thereto.
The hole transporting layer is a layer that receives holes from the hole injecting layer and transports the holes to the light emitting layer, and the hole transporting material is suitably a material having a large mobility to holes, which can receive holes from the anode or the hole injecting layer and transfer the holes to the light emitting layer. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, and the like, but are not limited thereto.
The electron blocking layer is a layer provided between the hole transport layer and the light emitting layer to prevent electrons injected in the cathode from being transferred to the hole transport layer without being recombined in the light emitting layer, and may also be referred to as an electron suppressing layer. The electron blocking layer is preferably a layer having a smaller electron affinity than the electron transport layer.
The luminescent material is preferably such a material: which can receive holes and electrons respectively transferred from the hole transport layer and the electron transport layer and combine the holes and electrons to emit light in the visible light region and have good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light emitting material include: 8-hydroxy-quinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; a dimeric styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzo Oxazole, benzothiazole-based and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) based polymers; a spiro compound; polyfluorene; rubrene; etc., but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of the heterocycle-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. In particular, the compound represented by chemical formula 1 may be included as a host.
Preferably, the light emitting layer may further include a compound represented by the following chemical formula 2.
[ chemical formula 2]
In the chemical formula 2, the chemical formula is shown in the drawing,
Ar 3 and Ar is a group 4 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 6 and R is 7 Each independently is hydrogen; deuterium; halogen; cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more selected from N, O and S 2-60 Heteroaryl group
p and q are each independently integers from 0 to 7.
Preferably Ar 3 And Ar is a group 4 May each independently be a substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 6-20 Heteroaryl groups.
More preferably Ar 3 And Ar is a group 4 May each independently be phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, or dimethylfluorenyl.
Most preferably Ar 3 And Ar is a group 4 Each independently is phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, or 9, 9-dimethyl-9H-fluorenyl.
Preferably, R 6 And R is 7 May each independently be hydrogen; substituted or unsubstituted C 1-20 An alkyl group; substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 6-20 Heteroaryl groups.
More preferably, R 6 And R is 7 Each may be hydrogen.
p and q fractionsR is represented by 6 And R is 7 And when p is 2 or greater, two or more R 6 May be the same or different from each other. When q is 2 or more, two or more R 7 May be the same or different from each other.
Representative examples of the compound represented by chemical formula 2 are as follows:
/>
/>
。
the compound represented by chemical formula 2 may be simultaneously contained in the organic material layer including the compound represented by chemical formula 1.
Preferably, the weight ratio of the compound represented by chemical formula 1 to the compound represented by chemical formula 2 may be 1:99 to 99:1, and more preferably 10:90 to 90:10.
Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a substituted or unsubstituted condensed aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styrylenediamine, styryltriamine, styryl Tetramine, etc., but is not limited thereto. Further, the metal complex includes iridium complex, platinum complex, and the like, but is not limited thereto.
The hole blocking layer is a layer provided between the electron transport layer and the light emitting layer to prevent holes injected in the anode from being transferred to the electron transport layer without being recombined in the light emitting layer, and may also be referred to as a hole suppressing layer. The hole blocking layer is preferably a layer having a large ionization energy.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is suitably a material such as: which can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and has a large electron mobility. Specific examples of the electron transport material include: al complexes of 8-hydroxyquinoline; comprising Alq 3 Is a complex of (a) and (b); an organic radical compound; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials having a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound of: it has an ability to transport electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated by the light emitting layer from moving to a hole injecting layer, and is also excellent in an ability to form a thin film. Specific examples of the electron injecting material include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives thereof, metal complexesAnd nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.
Examples of the metal complex compound include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (2-methyl-8-quinoline) chlorogallium, gallium bis (2-methyl-8-quinoline) (o-cresol), aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol), and the like.
The organic light emitting device according to the present invention may be of a front-side emission type, a rear-side emission type or a double-side emission type depending on the materials used.
Further, the compound represented by chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
Hereinafter, preferred embodiments of the present invention will be described in more detail to aid understanding of the present invention. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of the invention.
Preparation example 1: synthesis of intermediate A
(Synthesis of intermediate A-1)
2, 3-difluoro-1, 4-diiodobenzene (30.0 g,82.0 mmol), (4-chloro-2-methoxyphenyl) boronic acid (36.7 g,196.8 mmol), 2M Na 2 CO 3 Aqueous solution (164 mL,328.0 mmol), DME (165 mL), toluene (165 mL), pd (PPh) 3 ) 4 (9.5 g,8.2 mmol) was added to a three-necked flask, and the mixture was stirred under reflux for 8 hours under argon atmosphere. After the reaction was completed, the reaction temperature was cooled to room temperature, and then the reaction solution was transferred to a separating funnel. Adding H 2 O (300 mL) and CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Drying, filtering and concentrating, and then passing the sample through siliconPurification by column chromatography gave intermediate A-1 (21.1 g, yield: 65%).
MS[M+H] + ＝395。
(Synthesis of intermediate A-2)
Intermediate A-1 (20.0 g,50.6 mmol), CH 2 Cl 2 1M BBr in solution 3 (121 mL,121.4 mmol) and CH 2 Cl 2 (300 mL) was added to a two-necked flask, the temperature was adjusted to 0℃under an argon atmosphere, and the mixture was stirred for 8 hours. The reaction mixture was then stirred at room temperature for a further 4 hours, then with saturated NaHCO 3 And (5) neutralizing the aqueous solution. The reaction solution was transferred to a separatory funnel and treated with CH 2 Cl 2 And (5) extracting. The extract was purified by silica gel column chromatography to give intermediate A-2 (15.8 g, yield: 85%).
MS[M+H] + ＝367。
(Synthesis of intermediate A)
Intermediate A-2 (15.0 g,40.9 mmol), K 2 CO 3 (12.4 g,89.9 mmol) and NMP (170 mL) were added to the two-necked flask, and the mixture was stirred under argon at 150℃for 8 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and then the reaction solution was transferred to a separating funnel. Adding H 2 O (100 mL) and extracted with ethyl acetate. The extract was purified by silica gel column chromatography to obtain intermediate A (11.9 g, yield: 89%).
MS[M+H] + ＝327。
Preparation example 2: synthesis of intermediate B
(Synthesis of intermediate B-1)
Wherein 2, 5-dibromobenzene-1, 4-diol (20.0 g,74.7 mmol), (4-chloro-2-fluorophenyl) boronic acid (39.9 g,156.8 mmol) was dissolved in THF (750 mL) and K 2 CO 3 (61.9 g,447.9 mmol) in H 2 The solution in O (375 mL) was added to a three-necked flask. Pd (PPh) was added thereto 3 ) 4 (1.7 g,1.5 mmol) and the mixture was stirred under reflux for 8 hours under argon. After the reaction was completed, the reaction temperature was cooled to room temperature and the reaction solution was transferred to a separatory funnel and was purified by using CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Dried, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain intermediate B-1 (21.1 g, yield: 77%).
MS[M+H] + ＝367。
(Synthesis of intermediate B)
/>
Intermediate B-1 (15.0 g,40.9 mmol), K 2 CO 3 (12.4 g,89.9 mmol) and NMP (170 mL) were added to the two-necked flask, and the mixture was stirred under argon at 150℃for 8 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and then the sample was transferred to a separating funnel. To which H is added 2 O (100 mL) and extracted with ethyl acetate. The extract was purified by silica gel column chromatography to give intermediate B (10.8 g, yield: 81%).
MS[M+H] + ＝327。
Preparation example 3: synthesis of intermediate C
Intermediate C was prepared in the same manner as in the preparation method of intermediate a, except that 1, 5-dibromo-2, 4-difluorobenzene was used instead of 2, 3-difluoro-1, 4-diiodobenzene in preparation example 1.
MS[M+H] + ＝327。
Preparation example 4: synthesis of intermediate D
(Synthesis of intermediate D-1)
2-hydroxybenzo [ b, d]Furan (15.0 g,81.4 mmol) and acetic acid (100 mL) were added to a three-necked flask, to which iodine monochloride (4.5 mL,89.6 mmol), concentrated HCl (55 mL) and acetic acid solution (34 mL) were added dropwise and then stirred at room temperature for 24 hours. After the reaction was completed, H was added thereto 2 O (300 mL), and the resulting precipitate was filtered and taken up with H 2 And (3) washing. The filtered solid was recrystallized from MeOH to give intermediate D-1 (18.9 g, yield: 75%).
MS[M+H] + ＝310
(Synthesis of intermediate D-2)
Intermediate D-1 (18.0 g,58.0 mmol) and (4-chloro-2-fluorophenyl) boronic acid (10.6 g,61.0 mmol) were dissolved in THF (600 mL) and K 2 CO 3 (32.1 g,232.2 mmol) in H 2 The solution in O (300 mL) was added to a three-necked flask. Pd (PPh) was added thereto 3 ) 4 (0.7 g,0.6 mmol) and the mixture was stirred under reflux for 8 hours under argon. After the reaction was completed, the reaction temperature was cooled to room temperature and the reaction solution was transferred to a separatory funnel and was purified by using CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Dried, filtered and concentrated, and then the sample was purified by silica gel column chromatography to give intermediate D-2 (14.5 g, yield: 80%).
MS[M+H] + ＝313。
(Synthesis of intermediate D)
Intermediate D-2 (14.0 g,44.8 mmol), K 2 CO 3 (9.3 g,67.2 mmol) and NMP (180 mL) were added to the two-necked flask, and the mixture was stirred under argon at 150℃for 8 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and then the sample was transferred to a separating funnel. To which H is added 2 O (200 mL) and extracted with ethyl acetate. The extract was purified by silica gel column chromatography to give intermediate D (10.6 g, yield: 81%).
MS[M+H] + ＝293。
Preparation example 5: synthesis of intermediate E
(Synthesis of intermediate E-1)
3-fluorodibenzo [ b, d ]]Furan (15.0 g,80.6 mmol) and THF (400 mL) were added to a three-necked flask and cooled to-78 ℃. n-BuLi (1.6M in n-hexane, 55mL,88.6 mmol) was added dropwise and stirred at-78℃for 20 min. Triisopropylboric acid (45.5 g,241.7 mmol) was added and stirred at-78 ℃ for 1 hour, then further stirred at room temperature for 4 hours. Then, 1N HCl (130 mL) was added thereto and stirred at room temperature for 1 hour, and the reaction solution was concentrated and transferred to a separating funnel. Adding H 2 O (200 mL) and CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Dried, filtered, concentrated, and recrystallized from toluene-hexane to give intermediate E-1 (11.1 g, yield: 60%).
MS[M+H] + ＝230。
(Synthesis of intermediate E-2)
Intermediate E-1 (10.0 g,43.5 mmol) and 5-chloro-2-iodophenol (11.6 g,45.7 mmol) were isolated) Dissolved in THF (430 mL) and K 2 CO 3 (24.0 g,173.9 mmol) in H 2 The solution in O (220 mL) was added to a three-necked flask. Pd (PPh) was added thereto 3 ) 4 (0.5 g,0.4 mmol) and the mixture was stirred under reflux for 8 hours under argon. After the reaction was completed, the reaction temperature was cooled to room temperature and the reaction solution was transferred to a separatory funnel and was purified by using CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Dried, filtered and concentrated, and then the sample was purified by silica gel column chromatography to give intermediate E-2 (10.5 g, yield: 77%).
MS[M+H] + ＝313。
(Synthesis of intermediate E)
Intermediate E-2 (10.0 g,32.0 mmol), K 2 CO 3 (6.6 g,48.0 mmol) and NMP (130 mL) were added to the two-necked flask, and the mixture was stirred under argon at 150℃for 8 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and then the sample was transferred to a separating funnel. To which H is added 2 O (100 mL) and extracted with ethyl acetate. The extract was purified by silica gel column chromatography to give intermediate E (6.2 g, yield: 66%).
MS[M+H] + ＝293。
Preparation example 6: synthesis of intermediate F
Intermediate F was prepared in the same manner as in the preparation method of intermediate E, except that 3-fluorodibenzo [ b, d ] thiophene was used instead of 3-fluorodibenzo [ b, d ] furan in preparation example 5.
MS[M+H] + ＝309。
Preparation example 7: synthesis of Compound 1
(Synthesis of Compound 1-1)
Wherein intermediate A (15.0 g,45.8 mmol) and intermediate a-1 (17.3 g,48.1 mmol) were dissolved in THF (460 mL) and K 2 CO 3 (25.3 g,183.4 mmol) in H 2 The solution in O (230 mL) was added to a three-necked flask. Pd (PPh) was added thereto 3 ) 4 (0.5 g,0.5 mmol) and the mixture was stirred under reflux for 8 hours under argon. After the reaction was completed, the reaction temperature was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and was purified by using CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Dried, filtered and concentrated, and then the sample was purified by silica gel column chromatography to give compound 1-1 (16.3 g, yield: 68%).
MS[M+H] + ＝524。
(Synthesis of Compound 1)
In a three-necked flask, compound 1-1 (15.0 g,28.6 mmol) and intermediate b-1 (5.3 g,31.5 mmol) were dissolved in toluene (285 mL), and sodium t-butoxide (4.1 g,42.9 mmol) and bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) were added thereto. The mixture was stirred under reflux for 6 hours under argon. After the reaction was completed, the reaction temperature was cooled to room temperature, and H was added thereto 2 O (160 mL), and the reaction solution was transferred to a separatory funnel and extracted. The extract was treated with MgSO 4 Drying and concentrating. The sample was purified by silica gel column chromatography and then subjected to sublimation purification to obtain compound 1 (6.0 g, yield: 32%).
MS[M+H] + ＝655。
Preparation example 8: synthesis of Compound 2
Compound 2 was produced in the same manner as in the production method of compound 1, except that intermediate a-2 was used instead of intermediate a-1 in production example 7.
MS[M+H] + ＝731
Preparation example 9: synthesis of Compound 3
Compound 3 was produced in the same manner as in the production method of compound 1, except that intermediate a-3 was used instead of intermediate a-1 in production example 7.
MS[M+H] + ＝745
Preparation example 10: synthesis of Compound 4
Compound 4 was prepared in the same manner as in the preparation method of compound 1, except that intermediate B was used instead of intermediate a in preparation example 7.
MS[M+H] + ＝655
Preparation example 11: synthesis of Compound 5
/>
Compound 5 was produced in the same manner as in the production method of compound 1, except that intermediate B was used instead of intermediate a in production example 7 and intermediate a-4 was used instead of intermediate a-1 in production example 7.
MS[M+H] + ＝731
Preparation example 12: synthesis of Compound 6
Compound 6 was produced in the same manner as in the production method of compound 1, except that compound 4-1 was used instead of compound 1-1 in production example 7 and intermediate b-2 was used instead of intermediate b-1 in production example 7.
MS[M+H] + ＝731
Preparation example 13: synthesis of Compound 7
Compound 7 was prepared in the same manner as in the preparation method of compound 1, except that intermediate C was used instead of intermediate a in preparation example 7.
MS[M+H] + ＝655
Preparation example 14: synthesis of Compound 8
Compound 8 was produced in the same manner as in the production method of compound 1, except that compound 7-1 was used instead of compound 1-1 in production example 7 and intermediate b-3 was used instead of intermediate b-1 in production example 7.
MS[M+H] + ＝731
Preparation example 15: synthesis of Compound 9
Compound 9 was produced in the same manner as in the production method of compound 1, except that compound 7-1 was used instead of compound 1-1 in production example 7 and intermediate b-4 was used instead of intermediate b-1 in production example 7.
MS[M+H] + ＝731
Preparation example 16: synthesis of Compound 10
(Synthesis of Compound 10-1)
Wherein intermediate D (20.0 g,68.3 mmol) and intermediate a-1 (25.8 g,71.7 mmol) were dissolved in THF (680 mL) and K 2 CO 3 (37.8 g,273.3 mmol) in H 2 The solution in O (340 mL) was added to a three-necked flask. Pd (PPh) was added thereto 3 ) 4 (0.8 g,0.7 mmol) and the mixture was stirred under reflux for 8 hours under argon. After the reaction was completed, the reaction temperature was cooled to room temperature and the reaction solution was transferred to a separatory funnel and was purified by using CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Dried, filtered and concentrated, and then the sample was purified by silica gel column chromatography to give compound 10-1 (22.4 g, yield: 67%).
MS[M+H] + ＝490。
(Synthesis of Compound 10-2)
Compound 10-1 (20.0 g,40.9 mmol), NBS (8.0 g,44.9 mmol) and DMF (410 mL) were added to a two-necked flask, and the mixture was stirred at room temperature under argon for 8 hours. After the reaction was completed, the reaction solution was transferred to a separating funnel. To which H is added 2 O (200 mL) and extracted with ethyl acetate. The sample was purified by silica gel column chromatography to give compound 10-2 (19.0 g, yield 82%).
MS[M+H] + ＝568。
(Synthesis of Compound 10)
Compound 10-2 (18.0 g,31.7 mmol) and intermediate b-1 (5.8 g,34.8 mmol) was dissolved in toluene (320 mL). Sodium tert-butoxide (4.6 g,47.5 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.3 g,0.6 mmol) were added thereto, and the mixture was stirred under argon atmosphere at reflux for 6 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and H was added thereto 2 O (200 mL), and the reaction solution was transferred to a separatory funnel and extracted. The extract was treated with MgSO 4 Drying and concentrating. The sample was purified by silica gel column chromatography and then subjected to sublimation purification to obtain compound 10 (5.8 g, yield: 28%).
MS[M+H] + ＝655。
Preparation example 17: synthesis of Compound 11
Compound 11 was prepared in the same manner as in the preparation method of compound 10, except that intermediate E was used instead of intermediate D in preparation example 16.
MS[M+H] + ＝655
Preparation example 18: synthesis of Compound 12
(Synthesis of Compound 12-1)
Intermediate F (15.0 g,48.6 mmol) and intermediate b-1 (8.9 g,53.4 mmol) were dissolved in toluene (480 mL) in a three-necked flask. Sodium tert-butoxide (7.0 g,72.9 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.5 g,1.0 mmol) were added thereto, and the mixture was stirred under argon atmosphere at reflux for 6 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and H was added thereto 2 O (200 mL), and the reaction solution was transferred to a separatory funnel and extracted. The extract was treated with MgSO 4 Drying and concentrating. The sample was purified by silica gel column chromatography to obtain compound 12-1 (16.7 g, yield: 78%).
MS[M+H] + ＝440。
(Synthesis of Compound 12-2)
Compound 12-1 (16.0 g,36.4 mmol) was dissolved in THF (160 mL) under nitrogen in a dry three-necked flask, and 1.6M n-butyllithium (24 mL,38.2 mmol) was slowly added dropwise with stirring at-10 ℃. After completion of the dropwise addition, the mixture was further stirred at the same temperature for 4 hours, then the temperature was lowered to-78 ℃, trimethyl borate (4.9 g,47.3 mmol) was slowly added dropwise, the reaction temperature was allowed to rise to room temperature, and then the mixture was stirred overnight. After the reaction was completed, 2N aqueous HCl was added dropwise and acidified, followed by stirring for 30 minutes. The reaction solution was transferred to a separating funnel, and the organic layer was extracted with water and ethyl acetate, concentrated under reduced pressure, and recrystallized to give compound 12-2 (10.6 g, yield: 60%).
MS[M+H] + ＝483。
(Synthesis of Compound 12)
Wherein compound 12-2 (10.0 g,20.7 mmol) and intermediate a-5 (5.8 g,21.7 mmol) were dissolved in THF (200 mL) and K 2 CO 3 (11.4 g,82.8 mmol) dissolved in H 2 The solution in O (100 mL) was added to a three-necked flask. Pd (PPh) was added thereto 3 ) 4 (0.2 g,0.2 mmol) and the mixture was stirred under reflux for 8 hours under argon. After the reaction was completed, the reaction temperature was cooled to room temperature and the reaction solution was transferred to a separatory funnel and was purified by using CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 Dried, filtered and concentrated. The sample was purified by silica gel column chromatography and then subjected to sublimation purification to obtain compound 12 (4.6 g, yield: 33%).
MS[M+H] + ＝671
Preparation example 19: synthesis of Compound 13
Compound 13 was prepared in the same manner as in the preparation method of compound 1, except that intermediate G was used instead of intermediate a in preparation example 7.
MS[M+H] + ＝687
Preparation example 20: synthesis of Compound 14
Compound 14 was produced in the same manner as in the production method of compound 1, except that intermediate a-6 was used instead of intermediate a-1 in production example 7.
MS[M+H] + ＝665
Example 1
Coated with a coating having a thickness ofThe glass substrate as a thin film was put into distilled water in which a detergent was dissolved, and subjected to ultrasonic cleaning. At this time, a product manufactured by Fischer co. Was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore co. Was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice using distilled water for 10 minutes. After the washing with distilled water was completed, the substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents, dried, and then transferred to a plasma washer. In addition, the substrate was cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum depositor.
On the ITO transparent electrode thus prepared, the following compound HT-A and 5% by weight of the following compound PD were thermally vacuum depositedThen depositing only the following compounds HT-A to->To form a hole transport layer. Thermally vacuum depositing the following compound HT-B on the hole transport layer to +.>As an electron blocking layer. Then, vacuum deposition was performed to +.o.a. by using a host comprising the following compound PGH-1 as a first host and compound 1 of preparation example 7 as a second host in a weight ratio of 60:40 and 15 wt% of the following compound GD as a dopant>Is a thickness of (c). Then, the following compound ET-A was vacuum deposited to +.>As a hole blocking layer. Then, the following compounds ET-B and Liq were thermally vacuum deposited in a ratio of 2:1 to +.>As electron transport and injection layer, liF and magnesium are then vacuum deposited in a ratio of 1:1 to +.>Is a thickness of (c). Magnesium and silver are deposited on the electron transport and injection layer in a ratio of 1:4 to +.>To form a cathode, thereby completing the fabrication of the organic light emitting device.
Examples 2 to 20
Organic light emitting devices of examples 2 to 20 were manufactured in the same manner as in example 1, except that the host materials were changed as shown in table 1 below. In this case, when a mixture of two compounds is used as a host, brackets mean the weight ratio between the host compounds.
Comparative examples 1 to 6
Organic light emitting devices of comparative examples 1 to 6 were manufactured in the same manner as in example 1, except that the host materials were changed as shown in table 1 below. In this case, when a mixture of two compounds is used as a host, brackets mean the weight ratio between the host compounds. Compounds GH-A, GH-B, GH-C and GH-D in Table 1 are as follows.
Experimental example
The voltage, efficiency and lifetime (T95) were measured by applying current to the organic light emitting devices manufactured in examples 1 to 20 and comparative examples 1 to 6, and the results are shown in table 1 below. At this time, by applying 10mA/cm 2 Voltage and efficiency were measured, lifetime (T95) means at 20mA/cm 2 The time required for the luminance to decrease to 95% of the initial luminance at the current density of (c).
TABLE 1
As shown in table 1 above, it was confirmed that when the compound of chemical formula 1 was used as a host of the organic light emitting device, it exhibited low voltage, high efficiency, and long life characteristics. In particular, when used in combination with a compound of chemical formula 2 such as PGH-1, the effect becomes more prominent and it exhibits more excellent effects than when a compound of another structure is mixed with a compound of chemical formula 2.
[ description of reference numerals ]
1: substrate
2: anode
3: light-emitting layer
4: cathode electrode
5: hole transport layer
6: electron blocking layer
7: hole blocking layer
8: electron transport layer
9: electron injection layer
Claims (10)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein, in the chemical formula 1,
a is a benzene ring condensed with two adjacent rings,
X 1 and X 2 Each of which is O, and each of which is O,
Y 1 to Y 3 All of them are N, and the total number is N,
Ar 1 and Ar is a group 2 Each independently is phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, or phenyl substituted with 5 deuterium,
R 1 and R is 2 Each independently hydrogen, deuterium, or phenyl,
R 3 is hydrogen or deuterium, and is preferably selected from the group consisting of,
R 4 and R is 5 Each independently of the other is hydrogen or deuterium,
a and b are each independently integers from 0 to 4,
c is an integer of 0 to 2
d and e are each independently integers from 0 to 3.
2. The compound according to claim 1, wherein
Chemical formula 1 is represented by the following chemical formulas 1-1 to 1-6:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
Wherein, in chemical formulas 1-1 to 1-6,
X 1 、X 2 、Y 1 to Y 3 、Ar 1 、Ar 2 、R 1 To R 5 And a to e are the same as defined in claim 1.
3. The compound according to claim 1, wherein
Ar 1 And Ar is a group 2 At least one of the groups is phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenePhenyl, fluorenyl, or phenyl substituted with 5 deuterium.
4. The compound according to claim 1, wherein
The compound represented by chemical formula 1 is any one selected from the group consisting of:
/>
。
5. an organic light emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, wherein one or more of the layers of organic material comprises a compound according to any one of claims 1 to 4.
6. The organic light-emitting device of claim 5, wherein
The organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
7. The organic light-emitting device of claim 6, wherein
The light emitting layer further includes a compound represented by the following chemical formula 2:
[ chemical formula 2]
In the chemical formula 2, the chemical formula is shown in the drawing,
Ar 3 and Ar is a group 4 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 6 and R is 7 Each independently is hydrogen; deuterium; halogen; cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more selected from N, O and S 2-60 Heteroaryl group
p and q are each independently integers from 0 to 7.
8. The organic light-emitting device of claim 7, wherein
Ar 3 And Ar is a group 4 Each independently is phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, or dimethylfluorenyl.
9. The organic light-emitting device of claim 7, wherein
R 6 And R is 7 Each independently is hydrogen.
10. The organic light-emitting device of claim 7, wherein
The compound represented by chemical formula 2 is any one selected from the group consisting of:
/>
/>
。/>
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2018-0155293 | 2018-12-05 | ||
| KR20180155293 | 2018-12-05 | ||
| KR1020190139629A KR102362847B1 (en) | 2018-12-05 | 2019-11-04 | Novel compound and organic light emitting device comprising the same |
| KR10-2019-0139629 | 2019-11-04 | ||
| PCT/KR2019/015195 WO2020116800A1 (en) | 2018-12-05 | 2019-11-08 | Novel compound and organic light emitting diode comprising same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112739704A CN112739704A (en) | 2021-04-30 |
| CN112739704B true CN112739704B (en) | 2024-02-23 |
Family
ID=71081829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980061411.2A Active CN112739704B (en) | 2018-12-05 | 2019-11-08 | Novel compound and organic light emitting device comprising the same |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102362847B1 (en) |
| CN (1) | CN112739704B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115611919A (en) * | 2021-07-12 | 2023-01-17 | 广州华睿光电材料有限公司 | Organic compound containing heterocycle, mixture, composition and organic electronic device |
| KR20230087805A (en) * | 2021-12-10 | 2023-06-19 | 엘티소재주식회사 | Heterocyclic compound, organic light-emitting device comprising same and composition for organic material layer of organic light-emitting device comprising same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010045281A (en) * | 2008-08-18 | 2010-02-25 | Konica Minolta Holdings Inc | Organic electroluminescent element material, organic electroluminescent element, display, and lighting system |
| CN102017218A (en) * | 2008-05-08 | 2011-04-13 | 新日铁化学株式会社 | Organic electroluminescent element |
| CN102473859A (en) * | 2010-07-26 | 2012-05-23 | 出光兴产株式会社 | Organic electroluminescent element |
| KR20170086243A (en) * | 2016-01-18 | 2017-07-26 | 에스에프씨 주식회사 | Organic light-emitting compounds and Organic light-emitting device comprising the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100430549B1 (en) | 1999-01-27 | 2004-05-10 | 주식회사 엘지화학 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| US9209411B2 (en) * | 2012-12-07 | 2015-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2019
- 2019-11-04 KR KR1020190139629A patent/KR102362847B1/en active IP Right Grant
- 2019-11-08 CN CN201980061411.2A patent/CN112739704B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102017218A (en) * | 2008-05-08 | 2011-04-13 | 新日铁化学株式会社 | Organic electroluminescent element |
| JP2010045281A (en) * | 2008-08-18 | 2010-02-25 | Konica Minolta Holdings Inc | Organic electroluminescent element material, organic electroluminescent element, display, and lighting system |
| CN102473859A (en) * | 2010-07-26 | 2012-05-23 | 出光兴产株式会社 | Organic electroluminescent element |
| KR20170086243A (en) * | 2016-01-18 | 2017-07-26 | 에스에프씨 주식회사 | Organic light-emitting compounds and Organic light-emitting device comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20200068568A (en) | 2020-06-15 |
| CN112739704A (en) | 2021-04-30 |
| KR102362847B1 (en) | 2022-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112703189B (en) | Novel compound and organic light emitting device comprising the same | |
| CN112055705B (en) | Novel compound and organic light emitting device comprising the same | |
| CN112424183B (en) | Novel compound and organic light emitting device comprising the same | |
| CN111655683B (en) | Novel heterocyclic compound and organic light-emitting device comprising same | |
| CN112204034A (en) | Novel compound and organic light emitting device comprising the same | |
| CN112449639A (en) | Novel compound and organic light emitting device comprising the same | |
| CN110573494B (en) | Novel heterocyclic compound and organic light-emitting device comprising same | |
| CN112739704B (en) | Novel compound and organic light emitting device comprising the same | |
| CN113227081B (en) | Compound and organic light emitting device using the same | |
| CN113272307B (en) | Compound and organic light emitting device using the same | |
| CN112955455B (en) | Novel compound and organic light emitting device using the same | |
| CN112789272B (en) | Compound and organic light emitting device comprising the same | |
| CN111971281B (en) | Novel heterocyclic compound and organic light-emitting device comprising same | |
| CN111902407B (en) | Compound and organic light emitting device comprising the same | |
| CN117580834A (en) | Novel compound and organic light emitting device using the same | |
| CN117616025A (en) | Novel compound and organic light emitting device comprising the same | |
| CN113260608B (en) | Novel compound and organic light emitting device comprising the same | |
| CN113015728B (en) | Compound and organic light emitting device using the same | |
| CN113015729B (en) | Compound and organic light emitting device using the same | |
| CN116965179A (en) | Organic light emitting device | |
| CN116438154A (en) | Novel compound and organic light emitting device comprising the same | |
| CN111356696B (en) | Heterocyclic compound and organic light-emitting device comprising same | |
| CN113228336A (en) | Organic light emitting device | |
| CN114401961B (en) | Compound and organic light emitting device comprising the same | |
| CN111868053B (en) | Novel compound and organic light emitting device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |