CN115867555A - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
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- CN115867555A CN115867555A CN202180050031.6A CN202180050031A CN115867555A CN 115867555 A CN115867555 A CN 115867555A CN 202180050031 A CN202180050031 A CN 202180050031A CN 115867555 A CN115867555 A CN 115867555A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 82
- 239000010410 layer Substances 0.000 claims description 125
- -1 phenylnaphthyl group Chemical group 0.000 claims description 71
- 239000000126 substance Substances 0.000 claims description 69
- 239000012044 organic layer Substances 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 19
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 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 3
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 description 40
- 239000007924 injection Substances 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 230000032258 transport Effects 0.000 description 26
- 239000000463 material Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000001629 suppression Effects 0.000 description 7
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 6
- 229910052733 gallium Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- AEFBBDQSVSQZQD-UHFFFAOYSA-N 2-(2-chloro-1-benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(C(C(C=CC=C2)=C2O2)=C2Cl)OC1(C)C AEFBBDQSVSQZQD-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
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- 125000003277 amino group Chemical group 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-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
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-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
- 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 2
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-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
- 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 2
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001769 aryl amino 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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052796 boron Inorganic materials 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 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 2
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 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 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DLXBGTIGAIESIG-UHFFFAOYSA-N 1,8-dibromonaphthalene Chemical compound C1=CC(Br)=C2C(Br)=CC=CC2=C1 DLXBGTIGAIESIG-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- 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 group 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
- 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
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
The invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
This application claims priority based on korean patent application No. 10-2020-0120806, 18/2020 and korean patent application No. 10-2021-0105511, 8/11/2021, which are incorporated herein by reference in their entirety as part of the present specification.
The present invention relates to a novel compound and an organic light emitting device using the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2013-073537
Disclosure of Invention
Technical subject
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
X 1 、X 2 and X 3 Each independently O, S or CR, but one of which is O or S, where each R is independently hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, or combined with adjacent carbon atoms to form substituted or unsubstituted C 6-60 A fused ring,
l is a single bond; substituted or unsubstituted C 6-60 An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 A heteroarylene group, a heteroaryl group,
ar is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
R 1 each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
n is an integer of 0 to 8.
In addition, the present invention provides an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound of the present invention.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material for an organic layer of an organic light emitting device in which improvement in efficiency, lower driving voltage, and/or improvement in lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material of the light emitting layer.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
(description of wording)
In the context of the present specification,
represents a bond to other substituents. />
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium (D); 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 radicals
Arylthio radical->
Alkylsulfonyl radical or>
Aryl sulfonyl radical
A silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents selected from the group consisting of N, O and 1 or more heterocyclic groups containing S atoms, or substituted or unsubstituted by substituents formed by connecting 2 or more substituents among the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 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 compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, the 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 compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 40 carbon atoms. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. 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, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2,2-bis (biphenyl-1-yl) ethen-1-yl, stilbene-yl, styryl and the like, but the present invention is not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to an embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 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 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the compound may be
And the like. But is not limited thereto.
In this specification heteroaryl is taken to include 1 or more of O, N, si and SThe heterocyclic group as the hetero element in (b) is not particularly limited in the number of carbon atoms, but preferably has 2 to 60 carbon atoms. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Based on the combination of an azole radical and a sugar radical>
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo->
Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), thiazolyl, or isowurzitane>
Based on the combination of an azole radical and a sugar radical>
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, "heterocyclic aromatic ring" refers to a hetero-fused monocyclic or polycyclic ring which contains not less than 1 hetero atom of O, N and S as a ring-forming atom in addition to carbon atoms and has aromatic properties as a whole. The heterocyclic ring has 2 to 60, 2 to 30, or 2 to 20 carbon atoms, but is not limited thereto. Examples of the heterocyclic ring include a thiophene ring, a furan ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, and a dibenzothiophene ring, but the heterocyclic ring is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is exemplified by the same alkenyl groups as described above. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
(Compound (I))
The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 includes both a structure functioning as an electron acceptor and a structure functioning as an electron donor, and has a smaller band gap by exchanging charges inside a molecule because two units having completely different properties are directly bonded. This facilitates energy transfer to the red dopant, suitable for use as a host for a red light emitting layer in an organic light emitting device. In addition, five-membered condensed rings forming a seven-membered structure with benzocarbazole are included in the parent core structure functioning as an electron donor, and thus, the steric hindrance effect is small and higher stability is exhibited compared to other condensed ring structures (for example, six-membered rings). Thus, when the compound represented by chemical formula 1 is applied to an organic light emitting device, it may have high efficiency, low driving voltage, high luminance, long life, and the like. Observing the structure of chemical formula 1 is as follows:
in the above-mentioned chemical formula 1,
X 1 、X 2 and X 3 Each independently O, S or CR, but one of which is O or S, where each R is independently hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, or combined with adjacent carbon atoms to form substituted or unsubstituted C 6-60 A fused ring,
l is a single bond; substituted or unsubstituted C 6-60 An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 A heteroarylene group, a heteroaryl group,
ar is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
R 1 each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
n is an integer of 0 to 8.
Preferably, chemical formula 1 is a compound represented by the following chemical formulae 1-1 to 1-6:
in the above chemical formulas 1-1 to 1-6,
L、Ar、R 1 and n is as defined in claim 1,
each R' is independently hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
R 2 each independently is hydrogen; deuterium; substituted or unsubstituted C 6-30 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-30 (ii) a heteroaryl group, wherein,
m is an integer of 0 to 4.
Preferably, R 2 Each independently hydrogen, deuterium or phenyl.
Preferably, L is a single bond, or is selected from any one of the following:
in the above-mentioned group, the compound (A),
each R' is independently hydrogen, deuterium or phenyl,
a is each independently an integer of 0 to 4,
each b is independently an integer of 0 to 6.
Preferably, ar is selected from any one of the following:
in the above-mentioned group, the group,
X′ 1 、X′ 2 and X' 3 Each independently N or CH, but at least two of which are N,
each Y is independently O or S,
Ar 1 each independently is substituted or unsubstituted C 6-30 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-30 A heteroaryl group.
Preferably, ar 1 Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl, substituted or unsubstituted with one or more deuterium (D).
Most preferably, ar 1 Each independently is phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl, substituted or unsubstituted with one or more deuterium (D).
Preferably, R 1 Each independently hydrogen, deuterium or phenyl.
Specific examples of the compound represented by the above chemical formula 1 are shown below:
the compound represented by the above chemical formula 1 can be produced by the following reaction formula 1:
[ reaction formula 1]
In the above reaction formulae, each X' is independently a halogen, preferably bromine or chlorine, and the definitions of the remaining substituents are the same as those described above.
Specifically, the compound represented by the above chemical formula 1 is produced by combining the starting materials SM1 and SM2 through an amine substitution reaction. Such amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base. The reactive group used in the amine substitution reaction may be appropriately changed, and the method for producing the compound represented by chemical formula 1 may be further embodied in the synthesis examples described below.
(organic light emitting device)
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode disposed to face the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic 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, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include an electron inhibiting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include a hole inhibiting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer simultaneously performing electron transport and electron injection, and the electron transport layer, the electron injection layer, or the layer simultaneously performing electron transport and electron injection includes the compound represented by the above chemical formula 1.
In addition, the organic layer includes a hole injection layer, a hole transport layer, an electron suppression layer, and a light emitting layer, and any one or more selected from them includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1. Preferably, the compound represented by the above chemical formula 1 is used as a host compound of the light emitting layer.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device of a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an inverted (inverted type) organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure example of an organic light emitting device according to an embodiment of the present invention is shown in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as shown above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the structure as shown above, the compound represented by the above chemical formula 1 may be contained in 1 or more of the above hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole blocking layer, electron injection and transport layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by the above chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may form an organic layer not only by a vacuum evaporation method but also by a solution coating method in manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one 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.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO: al or SnO 2 : a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic 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, and alloys thereof; liF/Al or LiO 2 And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron inhibiting layer (or the electron blocking layer) is a layer interposed between the hole transporting layer and the light emitting layer in order to prevent electrons injected from the cathode from being transferred to the hole transporting layer without being recombined in the light emitting layer. The electron-suppressing layer is preferably a substance having a smaller electron affinity than the electron-transporting layer.
The light-emitting substance of the light-emitting layer is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq) 3 ) Carbazole-based compounds, dimerized styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light-emitting layer includes a host material and a dopant material, and the compound represented by chemical formula 1 of the present application is used as the host material or the red host material.
In addition to these, a host material may be further used, and for example, an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like may be included. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenopyrene, and the like, and the styrylamine compound is a compound substituted with at least 1 arylvinyl group on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The hole inhibiting layer (or hole blocking layer) refers to a layer in which: and a layer which is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and which serves to improve the efficiency of the organic light-emitting device by adjusting the electron mobility to prevent excessive hole migration and thereby increase the probability of hole-electron combination. The hole-inhibiting layer contains a hole-inhibiting substance, and examples of such hole-blocking substances include triazine-containing azine derivatives, triazole derivatives, and the like,
Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.
The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and functions as an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole-inhibiting layer. Such electron injection and transportThe substance is a substance that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a substance having a high mobility to electrons. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline, al complexes containing Alq 3 The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but are not limited thereto. Or may be reacted with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, or the like,
Azole and/or liquor>
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.
The electron injection and transport layer may be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, an electron transport layer is formed on the light-emitting layer or the hole-inhibiting layer, and the electron injection and transport material can be used as the electron transport material contained in the electron transport layer. Further, an electron injection layer is formed on the electron transport layer, and LiF, naCl, csF, li can be used as an electron injection substance contained in the electron injection layer 2 O, baO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and mixtures thereof,
Azole or in conjunction with a base>
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like.
Examples of the metal complex include, but are not limited to, lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinolinolato) chloride, gallium bis (2-methyl-8-quinolinolato) (o) gallium, bis (2-methyl-8-quinolinolato) (1-naphthol) aluminum, and gallium bis (2-methyl-8-quinolinolato) (2-naphthol) gallium.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The manufacture of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
[ Synthesis examples ]
Synthesis example a: synthesis of intermediate A
Step 1) Synthesis of intermediate A-1
1,8-dibromonaphthalene (1,8-dibromoaphtalene) (15.0 g,52.5 mmol) and (2-nitrophenyl) boronic acid (9.6 g,57.7 mmol) were added to 300ml THF under nitrogen, stirred and refluxed. Then, sodium hydroxide (8.4 g,209.8 mmol) was dissolved in 25ml of water and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (1.8 g,1.6 mmol) was charged.
After 10 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer and then distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.0g of intermediate A-1.
(yield 70%, MS: [ M + H ]] + ＝329)
Step 2) Synthesis of intermediate A-2
Intermediate A-1 (15.0g, 45.7mmol) and 2- (2-chlorobenzofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan (2- (2-chlorobenzofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan) (14.0g, 50.3mmol) were added to 300ml of THF under nitrogen, stirred and refluxed. Then, potassium carbonate (25.3g, 182.8mmol) was dissolved in 76ml of water and charged, followed by stirring sufficiently, and tetrakis (triphenylphosphine) palladium (0) (1.6g, 1.4 mmol) was charged. After 12 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was separated from the aqueous layer and then distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.9g of intermediate A-2.
(yield 65%, MS: [ M + H ]] + ＝401)
Step 3) Synthesis of intermediate A-3
Intermediate A-2 (15.0 g,37.5 mmol) was placed in 300ml 1,4-bis under nitrogen
The alkane (1,4-dioxane) was stirred under reflux. Then, potassium phosphate (9.6 g, 45mmol) was dissolved in 29ml of water and charged, and after sufficiently stirring, bis (dibenzylideneacetone) palladium (0) (bis (0)) (0.6 g,1.1 mmol) and tricyclohexylphosphine (0.6 g,2.3 mmol). The reaction was carried out for 5 hours, cooled to room temperature, and the organic layer was separated with chloroform and water, and then the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.4g of intermediate A-3.
(yield 69%, MS: [ M + H ]] + ＝364)
Step 3) Synthesis of intermediate A
Intermediate A-3 (20.0 g, 55mmol) and triethyl phosphite (13.7 ml,82.6 mmol) were stirred in 200ml o-dichlorobenzene (o-dichlorobenzzene) under nitrogen atmosphere while refluxing. After the reaction for 10 hours, the mixture was cooled to normal temperature, and the organic layer was separated from the water using chloroform and then distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.4g of intermediate a.
(yield 57%, MS: [ M + H ]] + ＝332)
Synthesis example B: synthesis of intermediate B
In synthetic example a, intermediate B was produced by the same production method as that of intermediate a except that 2- (2-chlorobenzofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was changed to 2- (3-chlorobenzofuran-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2- (3-chlorobenzofuran-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane).
(MS：[M+H] + ＝332)
Synthesis example C: synthesis of intermediate C
Intermediate C was produced by the same production method as that of intermediate A except that 2- (2-chlorobenzofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was changed to 2- (2-chlorobenzo [ b ] thiophen-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2- (2-chlorobenzo [ b ] thiophen-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane) and used in Synthesis example A.
(MS：[M+H] + ＝348)
Synthesis example D: synthesis of intermediate D
Intermediate D was produced by the same production method as that of intermediate A except that 2- (2-chlorobenzofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan was changed to 2- (3-chlorobenzo [ b ] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan (2- (3-chlorobenzo [ b ] thiophen-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan) and used in Synthesis example A.
(MS：[M+H] + ＝348)
Synthesis example E: synthesis of intermediate E
Intermediate E was produced by the same production method as that of intermediate A except that 2- (2-chlorobenzofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was changed to 2- (4-chlorofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2- (4-chlorofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane) and used in Synthesis example A.
(MS：[M+H] + ＝282)
Synthesis example F: synthesis of intermediate F
In Synthesis example A, intermediate F was produced by the same production method as that of intermediate A except that 2- (2-chlorobenzofuran-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was changed to 2- (4-chlorothiophen-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2- (4-chlorothiophen-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane).
(MS：[M+H] + ＝298)
Synthesis example 1: synthesis of Compound 1
Intermediate A (15.0 g,45.3 mmol) and intermediate a (12.0 g,49.8 mmol) were added to 300ml of xylene (xylene) under nitrogen, stirred and refluxed. Then, sodium tert-butoxide (6.5 g,67.9 mmol), bis (tri-tert-butylphosphine) palladium (0) (0.7 g,1.4 mmol) were added. After 8 hours of reaction, the mixture was cooled to normal temperature, and the organic layer was separated from the mixture with chloroform and water, and then the organic layer was distilled. The resulting solution was dissolved in chloroform again, washed with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography and then purified by sublimation to produce 8.7g of compound 1.
(yield 36%, MS: [ M + H ]] + ＝537)
Synthesis example 2: synthesis of Compound 2
(MS：[M+H] + ＝716)
Synthesis example 3: synthesis of Compound 3
(MS：[M+H] + ＝587)
Synthesis example 4: synthesis of Compound 4
(MS：[M+H] + ＝627)
Synthesis example 5: synthesis of Compound 5
Compound 5 was produced by the same production method as that of compound 1 except that in synthetic example 1, intermediate a was used instead of intermediate C and intermediate a was used instead of intermediate e.
(MS：[M+H] + ＝706)
Synthesis example 6: synthesis of Compound 6
Compound 6 was produced by the same production method as that of compound 1 except that in synthetic example 1, intermediate a was changed to intermediate D and intermediate a was changed to intermediate f for use.
(MS：[M+H] + ＝774)
Synthesis example 7: synthesis of Compound 7
(MS：[M+H] + ＝603)
Synthesis example 8: synthesis of Compound 8
Compound 8 was produced by the same production method as that of compound 1, except that in synthetic example 1, intermediate a was changed to intermediate E and intermediate a was changed to intermediate h.
(MS：[M+H] + ＝640)
Synthesis example 9: synthesis of Compound 9
Compound 9 was produced by the same production method as that of compound 1 except that in synthetic example 1, intermediate a was changed to intermediate F and intermediate a was changed to intermediate i and used.
(MS：[M+H] + ＝706)
[ examples and comparative examples ]
Comparative example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (2) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, a product of fisher (Fischer co.) was used as the detergent, and distilled water was filtered twice with a Filter (Filter) manufactured by Millipore co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, HI-A and hexanitrile hexaazatriphenylene (HAT-CN) described below were added in this order
The hole injection layer is formed by thermal vacuum deposition. On which, as hole transport layer, HT-A in the following manner is->
Vacuum vapor deposition was performed to ase:Sub>A thickness, and then EB-A described below was combined with an electron blocking layer to constitute ase:Sub>A receptor>
Thermal vacuum evaporation is performed to a thickness of (1). Next, as a light-emitting layer, the following host RH-A and 2wt% of a dopant RD are combined to->
Is thick to carry outAnd (4) vacuum evaporation. Next, as an electron transporting and injecting layer, ET-A and Liq described below are ^ treated in a ratio of 1: 1>
Is subjected to thermal vacuum deposition, and then Liq is expressed as->
Vacuum evaporation is performed to a thickness of (1). />
On the electron injection layer, magnesium and silver were sequentially mixed at a ratio of 10: 1
Thickness of aluminum and
the cathode is formed by vapor deposition to produce an organic light-emitting device.
Examples 1 to 9 and comparative examples 2 to 5
Organic light-emitting devices of examples 1 to 9 and comparative examples 2 to 3 were produced in the same manner as in comparative example 1, except that the compounds described in table 1 were used as the light-emitting layer host compound instead of RH-a in comparative example 1.
[ Experimental example ]
Experimental examples 1 to 9 and comparative Experimental examples 1 to 5
The organic light emitting devices fabricated in examples 1 to 9 and comparative examples 1 to 5 were applied with current, and the voltage, efficiency, and lifetime were measured, and the results are shown in table 1 below.
At this time, the voltage and efficiency were 10mA/cm 2 The life characteristic LT97 is at 20mA/cm 2 LT97 means the time when the initial luminance was reduced to 97%, measured at the current density of (2).
[ Table 1]
[ Table 1]
The compound of chemical formula 1 of the present application has a characteristic core structure and includes both a structure functioning as an electron acceptor and a structure functioning as an electron donor. Since the above-mentioned compound is directly bonded by two units having completely different properties, charges are exchanged inside the molecule to have a small band gap. This facilitates energy transfer to the red dopant, which is suitable for use as a host for the red light-emitting layer in an organic light-emitter.
As can be confirmed from the data of table 1, when the compound of chemical formula 1 of the present application is used, it is confirmed that the driving voltage is low, the efficiency is high, and the long life characteristic is realized. In particular, the compound of chemical formula 1 of the present application forms a fused seven-membered structure by benzocarbazole and a five-membered ring, thereby being compatible with an organic light emitting device using an RH-a compound that does not include a seven-membered structure inside a core; or an organic light emitting device using RH-B or RH-C comprising a seven-membered structure but comprising a benzene ring containing no hetero atom as a condensed ring; or an organic light emitting device using RH-D or RH-E to which no five-membered ring is fused was confirmed to exhibit low driving voltage, high efficiency, and long life characteristics.
Description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: an electron injection and transport layer.
Claims (9)
1. A compound represented by the following chemical formula 1:
in the chemical formula 1, the first and second organic solvents,
X 1 、X 2 and X 3 Each independently O, S or CR, but one of which is O or S, where each R is independently hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, or combined with adjacent carbon atoms to form substituted or unsubstituted C 6-60 A fused ring,
l is a single bond; substituted or unsubstituted C 6-60 An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 A heteroarylene group, a heteroaryl group,
ar is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
R 1 each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
n is an integer of 0 to 8.
2. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by the following chemical formula 1-1 to chemical formula 1-6:
in the chemical formulas 1-1 to 1-6,
L、Ar、R 1 and n is as defined in claim 1,
each R' is independently hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 (ii) a heteroaryl group, wherein,
R 2 each independently is hydrogen; deuterium; substituted or unsubstituted C 6-30 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-30 (ii) a heteroaryl group, wherein,
m is an integer of 0 to 4.
3. The compound of claim 1, wherein L is a single bond, or is selected from any one of the following:
in the context of the radical(s),
each R' is independently hydrogen, deuterium or phenyl,
a is each independently an integer of 0 to 4,
each b is independently an integer of 0 to 6.
4. The compound of claim 1, wherein Ar is any one selected from the group consisting of:
in the context of the radical(s),
X′ 1 、X′ 2 and X' 3 Each independently N or CH, but at least two of which are N,
each Y is independently O or S,
Ar 1 each independently substituted or unsubstituted C 6-30 An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-30 A heteroaryl group.
5. The compound of claim 4, wherein Ar 1 Each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, a phenanthryl group, a triphenylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazol-9-yl group, or a 9-phenyl-9H-carbazolyl group,
which are substituted or unsubstituted with more than one deuterium.
6. The compound of claim 1, wherein R 1 Each independently hydrogen, deuterium or phenyl.
7. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
8. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 7.
9. The organic light-emitting device according to claim 8, wherein the organic layer containing the compound is a light-emitting layer.
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