CN115551852A - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
- Publication number
- CN115551852A CN115551852A CN202180034264.7A CN202180034264A CN115551852A CN 115551852 A CN115551852 A CN 115551852A CN 202180034264 A CN202180034264 A CN 202180034264A CN 115551852 A CN115551852 A CN 115551852A
- Authority
- CN
- China
- Prior art keywords
- compound
- group
- layer
- organic layer
- organic
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 124
- 239000010410 layer Substances 0.000 claims description 124
- 239000012044 organic layer Substances 0.000 claims description 118
- 239000000126 substance Substances 0.000 claims description 83
- -1 naphthylphenyl Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 122
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 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 40
- 239000000203 mixture Substances 0.000 description 39
- 238000002347 injection Methods 0.000 description 36
- 239000007924 injection Substances 0.000 description 36
- 238000003756 stirring Methods 0.000 description 33
- 239000000706 filtrate Substances 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 239000012299 nitrogen atmosphere Substances 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- 229910000027 potassium carbonate Inorganic materials 0.000 description 21
- 230000032258 transport Effects 0.000 description 19
- 230000005525 hole transport Effects 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000004821 distillation Methods 0.000 description 15
- 239000000758 substrate Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229910052733 gallium Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 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 4
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 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
- 239000010405 anode material Substances 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 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
- 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- ATGAWOHQWWULNK-UHFFFAOYSA-I pentapotassium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [K+].[K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O ATGAWOHQWWULNK-UHFFFAOYSA-I 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- 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
- 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 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-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
- 125000005916 2-methylpentyl group Chemical group 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003277 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
- 125000005264 aryl amine group Chemical group 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
- 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
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000010408 film 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
- 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
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229910052744 lithium 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
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000011368 organic material Substances 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-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
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008569 process Effects 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
- 230000004044 response Effects 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 125000001544 thienyl group Chemical group 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
- 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 1
- 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 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- UJOBWOGCFQCDNV-PGRXLJNUSA-N 1,2,3,4,5,6,7,8-octadeuterio-9h-carbazole Chemical compound [2H]C1=C([2H])C([2H])=C2C3=C([2H])C([2H])=C([2H])C([2H])=C3NC2=C1[2H] UJOBWOGCFQCDNV-PGRXLJNUSA-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
- DNFDDDWPODPCHU-UHFFFAOYSA-N 2-bromo-6-fluorophenol Chemical compound OC1=C(F)C=CC=C1Br DNFDDDWPODPCHU-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- KTTRHLOWOKRRKS-UHFFFAOYSA-N 2-chloro-4-naphthalen-2-yl-6-phenyl-1,3,5-triazine Chemical compound C1(=NC(C2=CC=CC=C2)=NC(=N1)C1=CC=C2C(C=CC=C2)=C1)Cl KTTRHLOWOKRRKS-UHFFFAOYSA-N 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
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- JIHNZNBRECXPJB-UHFFFAOYSA-N 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)carbazole Chemical compound N=1C(N2C3=CC=CC=C3C3=CC=CC=C32)=NC(Cl)=NC=1C1=CC=CC=C1 JIHNZNBRECXPJB-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 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
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 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
- 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
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 125000003609 aryl vinyl 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 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
- 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
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125773 compound 10 Drugs 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
- 125000004093 cyano group Chemical group *C#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
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002219 fluoranthenes Chemical class 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 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
- 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
- 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
- 150000002503 iridium Chemical class 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
- 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 1
- 239000011133 lead Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 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 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
- 150000005041 phenanthrolines 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 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
- 150000004032 porphyrins Chemical class 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
- 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 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
- 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 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
- 239000010409 thin film Substances 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
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 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
- 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 238000007738 vacuum evaporation 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
- 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
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2020-0097603 on 8/4/2020 and korean patent application No. 10-2021-0101875 on 8/3/2021, the entire contents disclosed in the documents of the korean patent application are incorporated herein by reference.
The present invention relates to a novel compound and an organic light emitting device including 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 literature
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical subject matter
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 relates to a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-described chemical formula 1,
x is N or CH, 2 or more of the above-mentioned X's are N,
y is O or S, and Y is O or S,
L 1 is a direct bond, or a substituted or unsubstituted C 6-60 An arylene group, a heterocyclic group, or a heterocyclic group,
L 2 is a direct bond, or a substituted or unsubstituted C 6-60 An arylene group, a cyclic or cyclic alkylene group,
Ar 1 and Ar 2 Each independently 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 6-60 (ii) a heteroaryl group, wherein,
R 1 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 6-60 (ii) a heteroaryl group, wherein,
R 2 each independently of the other is hydrogen or deuterium,
but Ar 1 、Ar 2 And R 1 Is substituted by more than one deuterium, or R 2 Is deuterium.
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 for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
The following description is made in more detail to help understanding of the present invention.
(definition of wording)
In the context of the present specification,
and
represents a bond to another substituent.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a cyano 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 radicals
Alkyl sulfonyl radical
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 of 1 or more heteroaryl groups containing N, O and S atoms, or substituted or unsubstituted by substituents formed by linking 2 or more substituents of the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are bonded" 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 40. 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-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, 2-methylpentyl, 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 above 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-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, 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 one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. 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 may be 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 having aromaticity. 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. As the above-mentioned polycyclic aromatic group, can be naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, perylenyl,
But is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazino-pyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), and isooxazolyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the aryl group described above. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the 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 heteroaryl 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 heteroaryl 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 this specification, the heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and in addition to this, the above description on the heteroaryl group can be applied.
(Compound (I))
The present invention provides a compound represented by the above chemical formula 1.
The following describes the chemical formula 1 and the compound represented by the chemical formula in detail.
Each X is independently N or CH, and 2 or more of the above-mentioned X's are N.
Specifically, X may be all N.
Ar 1 And Ar 2 Each independently may be 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 6-60 A heteroaryl group.
Specifically, ar 1 And Ar 2 Each independently may be phenyl, biphenyl, naphthyl, naphthylphenyl, phenanthryl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, dibenzofuranyl or dibenzothiophenyl. Wherein, ar is 1 And Ar 2 Unsubstituted or substituted with more than one deuterium.
For example, ar 1 And Ar 2 Each independently may be unsubstituted biphenyl, naphthyl, phenanthryl, naphthylphenyl, dibenzofuranyl, dibenzothienyl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, or phenyl which is unsubstituted or substituted with 5 deuterium.
L 1 May be a direct bond, or a substituted or unsubstituted C 6-60 An arylene group.
For example, L 1 May be a direct bond, phenylene, biphenylene or naphthylene.
L 2 May be a direct bond, or a substituted or unsubstituted C 6-60 An arylene group.
For example, L 1 Either a direct bond or a phenylene group.
Y is O or S, and may be O, for example.
R 1 May be 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 6-60 A heteroaryl group.
For example, R 1 Is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl or dibenzothienyl, R is as defined above 1 May be unsubstituted or substituted with more than one deuterium.
R 2 Each independently may be hydrogen or deuterium.
But chemical formula 1 satisfies the above definition while Ar 1 、Ar 2 And R 1 Is substituted with more than one deuterium, or R 2 Is deuterium.
As a more specific example, the compound represented by the above chemical formula 1 may be any one selected from the following compounds:
the present invention also provides a method for producing the compound represented by the above chemical formula 1, as shown in the following reaction formula 1.
[ reaction formula 1]
In the above reaction formula 1, X, Y, L 1 、L 2 、Ar 1 、Ar 2 、R 1 And R 2 Is the same as that of chemical formula 1. In addition, in reaction formula 1, Z is halogen, preferably chlorine.
The above reaction formula 1 is a suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the suzuki coupling reaction may be modified according to a technique known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
(organic light emitting device)
In another aspect, 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, but 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, a light emitting 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 a light emitting layer including the compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, but may be formed of 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, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger number of organic layers may be included.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on the substrate (normal type). In addition, the organic light emitting device according to the present invention may be an inverted (inverted) type organic light emitting device in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on the substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated 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 hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole transport layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole injection layer, hole transport layer, or electron suppression 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 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 (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 species is between the work function of the anode species 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. As the hole transporting substance, a compound represented by the above chemical formula 1, an arylamine organic substance, a conductive polymer, a block copolymer in which a conjugated portion and a non-conjugated portion coexist, or the like can be used, but the hole transporting substance is not limited thereto.
The electron-suppressing layer is a layer including: and a layer which is formed on the hole transport layer, is preferably provided in contact with the light-emitting layer, and serves to prevent excessive electron transfer by adjusting hole mobility, thereby increasing the probability of hole-electron combination, and thus improving the efficiency of the organic light-emitting device. The electron-inhibiting layer contains an electron-blocking substance, and examples of such electron-blocking substances include, but are not limited to, compounds represented by the above chemical formula 1, arylamine-based organic substances, and the like.
The light-emitting substance is a substance that can emit light in the visible light region by receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, 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 may contain a host material and a dopant material as described above. The host material may further include an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like. 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 a compound having a substituted or unsubstituted aryl groupAromatic fused ring derivatives of amino group including pyrene, anthracene, having arylamino group,
And 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 aryl, silyl, alkyl, cycloalkyl, and arylamino. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrriamine, and styryltretraamine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The 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 prevent excessive hole migration by adjusting the electron mobility, thereby increasing the probability of hole-electron combination, thereby improving the efficiency of the organic light-emitting layer device. The hole-blocking layer contains a hole-blocking substance, and as examples of such hole-blocking substances, azine derivatives including triazine, triazole derivatives, and the like can be used,
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 blocking layer. Such an electron injecting and transporting substance is a substance that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for 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 A complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but is not limited thereto. OrThey may be reacted with fluorenone, anthraquinone dimethane, or mixtures thereof diphenoquinone, thiopyran dioxide,
Azole,
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.
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 Bottom emission (Bottom emission) device, a Top emission (Top emission) device, or a bi-directional light emitting device, and particularly, may be a Bottom emission device requiring relatively high light emitting efficiency.
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.
[ production example ]
Production example 1: production of Compound substance (sub) 1-2
First, compound A-1 was produced.
2-bromo-6-fluorophenol (100g, 526.5 mmol) and (4-chloro-2-fluorophenyl) boronic acid (91.6 g,526.5 mmol) were added to tetrahydrofuran (2000 ml) under nitrogen, refluxed and stirred. Then, potassium carbonate (218.3g, 1579.4mmol) was dissolved in water (218 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (18.2g, 15.8mmol) was charged. After 1 hour of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in chloroform (6739 mL), washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a gray solid compound A-1 (99.7 g, yield 74%, MS: [ M + H ]] + ＝257)。
Then, compound A-2 was produced.
A-1 (70g, 273.4 mmol) and N-bromosuccinimide (48.7 g,273.4 mmol) were added to chloroform (350 ml) under nitrogen, stirred and cooled to 0 ℃. After the reaction for 1 hour, the reaction mixture was cooled to room temperature and then poured into water. Then, the organic layer and the aqueous layer were separated, and the organic layer was concentrated. This was added again to chloroform (913 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by means of a silica gel column using chloroform and ethyl acetate to obtain Compound A-2 (65.7 g, yield 72%, MS: [ M + H ]] + ＝334.9)。
Then, compound A-3 was produced.
A-2 (50g, 149.7 mmol) was added to dimethylformamide (250 ml) under nitrogen, potassium carbonate was added, stirred and heated to 140 ℃. Then, after 7 hours of reaction, the reaction mixture was cooled to room temperature and then poured into water. The resulting solid was then filtered. The resulting solution was added again to chloroform (380 mL) and dissolved, and the solution was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirredThen, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to obtain a white solid compound A-2 (27 g, yield 71%, MS: [ M + H ]] + ＝255)。
Then, compound A-4 was produced.
A-3 (20g, 67.1mmol) and phenylboronic acid (8.2g, 67.1mmol) were added to tetrahydrofuran (400 ml) under a nitrogen atmosphere, and refluxed and stirred. Then, potassium carbonate (27.8g, 201.4mmol) was dissolved in water (28 ml), and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (0) (2.3g, 2mmol) was charged. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was dissolved in chloroform (397 mL) again, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound A-4 (14.9 g, yield 75%, MS: [ M + H ]] + ＝297)。
Then, compound substance 1-1 was produced.
A-4 (15g, 50.7mmol) and 9H-carbazole-1, 3,4,5,6,8-D6 (8.8g, 50.7mmol) were added to dimethylformamide (300 ml) under a nitrogen atmosphere, stirred and refluxed. Then, potassium triphosphate (32.3 g, 152mmol) was added thereto, the mixture was sufficiently stirred, the reaction mixture was cooled to normal temperature after 3 hours, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again poured into chloroform (228 mL) to dissolve it, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to produce a white solid compoundSubstance 1-1 (16.8 g, yield 74%, MS: [ M + H ]] + ＝450.2)。
Then, compound substance 1-2 was produced.
Under nitrogen, the substances 1-1 (15g, 33.4 mmol) and bis (pinacolato) diboron (9.3g, 36.7 mmol) were added to the di
In an alkane (300 ml), stirred and refluxed. Next, potassium acetate (9.6 g, 100.2mmol) was charged, and after sufficiently stirring, bis (dibenzylideneacetone) palladium (0) (0.6 g, 1mmol) and tricyclohexylphosphine (0.6 g, 2mmol) were charged. After 7 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and then the organic layer was distilled. This was again poured into chloroform (181 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give white solid compound substance 1-2 (15.9 g, yield 88%, MS: [ M + H ]] + ＝542.3)。
Production example 2: production of Compound substance 2-2
First, compound substance 2-1 was produced.
A-4 (15g, 50.7mmol) and 9H-carbazole-1, 2,3,4,5,6,7,8-D8 (8.9g, 50.7mmol) were added to dimethylformamide (300 ml) under nitrogen, stirred and refluxed. Then, potassium triphosphate (32.3 g, 152mmol) was added thereto, the mixture was sufficiently stirred, reacted for 7 hours, cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again poured into chloroform (229 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. Will be provided withThe concentrated compound was purified by means of a silica gel column using chloroform and ethyl acetate to give 1-2 (13.7 g, yield 60%, MS: [ M + H ])] + ＝452.2)。
Then, compound substance 2-2 was produced.
Under nitrogen, the substance 2-1 (15g, 33.2mmol) and bis (pinacolato) diboron (9.3g, 36.6 mmol) were added to the di
In an alkane (300 ml), stirred and refluxed. Then, potassium acetate (9.6 g,99.7 mmol) was charged, and after sufficiently stirring, bis (dibenzylideneacetone) palladium (0) (0.6 g, 1mmol) and tricyclohexylphosphine (0.6 g, 2mmol) were charged. After 6 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and then the organic layer was distilled. This was again poured into chloroform (181 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give white solid compound substance 2-2 (10.3 g, yield 57%, MS: [ M + H ]] + ＝544.3)。
Production example 3: production of Compound substance 3-2
First, compound B-1 was produced.
A-3 (20g, 67.1mmol) and [1,1' -biphenyl were mixed under a nitrogen atmosphere]-3-Ylboronic acid (13.3g, 67.1mmol) was added to tetrahydrofuran (400 ml), refluxed and stirred. Then, potassium carbonate (27.8g, 201.4mmol) was dissolved in water (28 ml), and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (0) (2.3g, 2mmol) was charged. After the reaction for 1 hour, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. It is put intoThe resulting solution was dissolved in chloroform (500 mL) again, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give white solid compound B-1 (16.2 g, yield 65%, MS: [ M + H ]] + ＝373.1)。
Then, compound substance 3-1 was produced.
B-1 (15g, 40.3mmol) and 9H-carbazole-1, 3,4,5,6,8-D6 (7g, 40.3mmol) were added to dimethylformamide (300 ml) under nitrogen atmosphere, stirred and refluxed. Then, potassium triphosphate (25.7g, 120.9 mmol) was added thereto, and after stirring sufficiently, the reaction was carried out for 6 hours, and then cooled to room temperature, and the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again poured into chloroform (213 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by means of a silica gel column using chloroform and ethyl acetate to produce 3-1 (15.3 g, yield 72%, MS: [ M + H ]] + ＝529.2)。
Then, compound substance 3-2 was produced.
Under nitrogen atmosphere, the substances 3-1 (15g, 28.6 mmol) and bis (pinacolato) diboron (8g, 31.4 mmol) were added to a bis
In an alkane (300 ml), stirred and refluxed. Then, potassium acetate (8.2 g,85.7 mmol) was charged, and after sufficiently stirring, bis (dibenzylideneacetone) palladium (0) (0.5g, 0.9mmol) and tricyclohexylphosphine (0.5g, 1.7 mmol) were charged. After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove saltsThe organic layer was distilled. This was again poured into chloroform (176 mL) to dissolve it, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give 3-2 (8.8 g, yield 50%, MS: [ M + H ])] + ＝618.3)。
Production example 4: production of Compound substance 4-2
First, compound C-1 was produced.
A-3 (20g, 67.1mmol) and dibenzo [ b, d ] were mixed in a nitrogen atmosphere]Furan-4-ylboronic acid (14.2g, 67.1mmol) was added to tetrahydrofuran (400 ml), refluxed and stirred. Then, potassium carbonate (27.8g, 201.4mmol) was dissolved in water (28 ml), and after stirring sufficiently, tetrakis (triphenylphosphine) palladium (0) (2.3g, 2mmol) was charged. After 1 hour of the reaction, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again poured into chloroform (518 mL) to dissolve it, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give white solid compound C-1 (20.2 g, yield 78%, MS: [ M + H ]] + ＝387.1)。
Then, the compound substance 4-1 was produced.
C-1 (15g, 38.9 mmol) and 9H-carbazole-1, 3,4,5,6,8-D6 (6.7g, 38.9 mmol) were added to dimethylformamide (300 ml) under a nitrogen atmosphere, stirred and refluxed. Then, potassium tripolyphosphate (24.7g, 116.6 mmol) was added thereto, and after stirring sufficiently, reaction was carried out for 3 hours, then cooling was carried out to normal temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was again poured into chloroform (209 mL)After dissolving, the mixture was washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was purified by means of a silica gel column using chloroform and ethyl acetate to produce 4-1 (12.6 g, yield 60%, MS: [ M + H ])] + ＝540.2)。
Then, compound substance 4-2 was produced.
Under nitrogen, the materials 4-1 (15g, 27.8mmol) and bis (pinacolato) diboron (7.8g, 30.6mmol) were added to the bis
In an alkane (300 ml), stirred and refluxed. Then, potassium acetate (8g, 83.5mmol) was charged, and after sufficient stirring, bis (dibenzylideneacetone) palladium (0) (0.5g, 0.8mmol) and tricyclohexylphosphine (0.5g, 1.7 mmol) were charged. After 6 hours of reaction, the reaction mixture was cooled to normal temperature, and the organic layer was filtered to remove salts, and then the organic layer was distilled. This was again poured into chloroform (176 mL) to dissolve it, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give 4-2 (9.8 g, yield 56%, MS: [ M + H ]] + ＝632.3)。
[ examples ]
Example 1: synthesis of Compound 1
The materials 1-2 (10g, 18.5mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (4.9g, 18.5mmol) were added to tetrahydrofuran (200 ml) under a nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mm) was chargedol). After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again dissolved in chloroform (238 mL), 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 recrystallized from chloroform and ethyl acetate to give Compound (Compound) 1 (7 g, yield 59%, MS: [ M + H ]] + ＝646.3)。
Example 2: synthesis of Compound 2
Under nitrogen atmosphere, materials 1-2 (10g, 18.5mmol) and 2- ([ 1,1' -biphenyl) were added]-4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (6.3g, 18.5 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, followed by sufficient stirring, and tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6mmol) was charged. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again dissolved in chloroform (267 mL), 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 recrystallized from chloroform and ethyl acetate to give Compound 2 (8.4 g, yield 63%, MS: [ M + H ]] + ＝723.3)。
Example 3: synthesis of Compound 3
Under nitrogen atmosphere, materials 1-2 (10g, 18.5mmol) and 2- ([ 1,1' -biphenyl) were added]-3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (6.3g, 18.5 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol) was charged. After 2 hours of reactionAfter cooling to room temperature, the organic layer was separated from the aqueous layer, and the organic layer was distilled. This was added again to chloroform (267 mL) to dissolve the precipitate, the solution was washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 3 (6.9 g, yield 52%, MS: [ M + H ]] + ＝723.3)。
Example 4: synthesis of Compound 4
The materials 1-2 (10g, 18.5mmol) and 2-chloro-4- (naphthalen-2-yl) -6-phenyl-1, 3, 5-triazine (5.9g, 18.5mmol) were added to tetrahydrofuran (200 ml) under a nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol) was charged. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again dissolved in chloroform (257 mL), 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 recrystallized from chloroform and ethyl acetate to give Compound 4 (7.2 g, yield 56%, MS: [ M + H ]] + ＝697.3)。
Example 5: synthesis of Compound 5
Under nitrogen atmosphere, materials 1-2 (10g, 18.5mmol) and 2-chloro-4- (dibenzo [ b, d ] were mixed]Furan-4-yl) -6-phenyl-1, 3, 5-triazine (6.6 g,18.5 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol) was charged. After reacting for 3 hours, cooling to normal temperature, and adding organic solventAfter separation of the layers from the aqueous layer, the organic layer was distilled. This was again poured into chloroform (272 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 5 (8.4 g, yield 62%, MS: [ M + H ]] + ＝737.3)。
Example 6: synthesis of Compound 6
Under nitrogen atmosphere, substances 1-2 (10g, 18.5mmol) and 2-chloro-4- (dibenzo [ b, d ] were mixed]Furan-3-yl) -6-phenyl-1, 3, 5-triazine (6.6 g,18.5 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol) was charged. After 1 hour of the reaction, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again dissolved in chloroform (272 mL), 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 recrystallized from chloroform and ethyl acetate to give Compound 6 (9.8 g, yield 72%, MS: [ M + H ]] + ＝737.3)。
Example 7: synthesis of Compound 7
Under nitrogen atmosphere, substances 1-2 (10g, 18.5mmol) and 2-chloro-4- (dibenzo [ b, d ] were mixed]Furan-2-yl) -6-phenyl-1, 3, 5-triazine (6.6 g,18.5 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, followed by sufficient stirring, and tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6mmol) was charged. After reacting for 3 hours, cooling to normal temperature, separating the organic layer from the aqueous layerAfter that, the organic layer was distilled. This was again dissolved in chloroform (272 mL), 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 recrystallized from chloroform and ethyl acetate to give Compound 7 (10.6 g, yield 78%, MS: [ M + H ]] + ＝737.3)。
Example 8: synthesis of Compound 8
Under nitrogen atmosphere, substances 1-2 (10g, 18.5mmol) and 2-chloro-4- (dibenzo [ b, d ] were mixed]Furan-1-yl) -6-phenyl-1, 3, 5-triazine (6.6 g,18.5 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol) was charged. After the reaction for 1 hour, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again poured into chloroform (272 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 8 (7.9 g, yield 58%, MS: [ M + H ] (light yellow, solid, MS)] + ＝737.3)。
Example 9: synthesis of Compound 9
Under nitrogen atmosphere, substances 1-2 (10g, 18.5mmol) and 2-chloro-4- (dibenzo [ b, d ] were mixed]Thien-4-yl) -6-phenyl-1, 3, 5-triazine (6.9g, 18.5 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol) was charged. After reacting for 1 hour, cooling to room temperature, separating organic layer and water layer, distillingAnd (4) a machine layer. This was again poured into chloroform (278 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 9 (11 g, yield 79%, MS: [ M + H ]] + ＝753.3)。
Example 10: synthesis of Compound 10
The substances 1-2 (10g, 18.5mmol) and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole (6.6g, 18.5mmol) were added to tetrahydrofuran (200 ml) under a nitrogen atmosphere, and stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, followed by sufficient stirring, and tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6mmol) was charged. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water layer, followed by distillation of the organic layer. This was again poured into chloroform (272 mL) and dissolved, and the mixture was washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 10 (10.7 g, yield 79%, MS: [ M + H ]] + ＝736.3)。
Example 11: synthesis of Compound 11
Under a nitrogen atmosphere, the substances 1-2 (10g, 18.5mmol) and 2-chloro-4-phenyl-6- (phenyl-D5) -1,3, 5-triazine (5g, 18.5mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, followed by stirring well, and tetrakis (triphenylphosphine) palladium (0.6g, 0.6mmol) was charged. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again poured into chloroform (241 mL)After dissolving, washing with water for 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirring was performed, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 11 (9.3 g, yield 77%, MS: [ M + H ]] + ＝652.3)。
Example 12: synthesis of Compound 12
The substances 1-2 (10g, 18.5mmol) and 2-chloro-4, 6-bis (phenyl-D5) -1,3, 5-triazine (5.1g, 18.5mmol) were added to tetrahydrofuran (200 ml) under a nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (7.7g, 55.4mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.6 mmol) was charged. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water layer, followed by distillation of the organic layer. This was again poured into chloroform (243 mL) to dissolve it, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce compound 12 (8.5 g, yield 70%, MS: [ M + H ] + = 657.3) as a pale yellow solid.
Example 13: synthesis of Compound 13
Under a nitrogen atmosphere, substance 2-2 (10g, 18.4mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (4.9g, 18.4mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.6 g, 55.2mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.6 mmol) was charged. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water layer, followed by distillation of the organic layer. Dissolving the mixture in chloroform (239 mL) again, washing with water for 2 times, separating the organic layer, and adding anhydrous sulfuric acidMagnesium, stirring and filtering, and distilling the filtrate under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 13 (6.8 g, yield 57%, MS: [ M + H ]] + ＝649.3)。
Example 14: synthesis of Compound 14
Under a nitrogen atmosphere, substances 2-2 (10g, 18.4mmol) and 2- ([ 1,1' -biphenyl) were added]-3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (6.3g, 18.4 mmol) was added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (7.6 g, 55.2mmol) was dissolved in water (8 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6 g,0.6 mmol) was charged. After the reaction for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the water layer, followed by distillation of the organic layer. This was added again to chloroform (267 mL) to dissolve the precipitate, the solution was washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 14 (7.1 g, yield 53%, MS: [ M + H ]] + ＝725.3)。
Example 15: synthesis of Compound 15
Under nitrogen, the substances 3-2 (10g, 16.2mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (4.3g, 16.2mmol) were added to tetrahydrofuran (200 ml), stirred and refluxed. Then, potassium carbonate (6.7g, 48.6mmol) was dissolved in water (7 ml) and charged, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (0) (0.6g, 0.5mmol) was charged. After 1 hour of the reaction, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. The resulting solution was added again to chloroform (234 mL) and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give Compound 15 (6.6 g, yield 56%, MS: [ M + H ]] + ＝723.3)。
Example 16: synthesis of Compound 16
The substance 4-2 (10g, 15.6 mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (4.2g, 15.6 mmol) were added to tetrahydrofuran (200 ml) under a nitrogen atmosphere, and stirred and refluxed. Then, potassium carbonate (6.5g, 46.8mmol) was dissolved in water (6 ml) and charged, and after sufficient stirring, tetrakis (triphenylphosphine) palladium (0) (0.5g, 0.5mmol) was charged. After reacting for 2 hours, the reaction mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer, followed by distillation of the organic layer. This was again dissolved in chloroform (230 mL), 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 recrystallized from chloroform and ethyl acetate to give Compound 16 (5.9 g, yield 51%, MS: [ M + H ]] + ＝737.3)。
[ Experimental example ]
Experimental example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) 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 such as isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. Further, after the substrate was cleaned for 5 minutes by oxygen plasma, the substrate was transferredSending to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following HI-1 compound was added
The hole injection layer is formed by thermal vacuum deposition to a thickness of (3). On the hole injection layer, the following HT-1 compound is added
A hole transport layer is formed by thermal vacuum deposition, and the following HT-2 compound is deposited on the HT-1 deposited film
The electron blocking layer is formed by vacuum evaporation. On the HT-2 deposited film, the compound 1 produced in example 1, the following YGH-1 compound, and the phosphorescent dopant YGD-1 were co-deposited at a weight ratio of 44
A thick light emitting layer.
On the light-emitting layer, the following ET-1 compound is added
The electron transporting layer was formed by vacuum vapor deposition, and the following ET-2 compound and Li were vacuum vapor deposited on the electron transporting layer at a weight ratio of 98
A thick electron injection layer. On the electron injection layer, to
The cathode is formed by vapor deposition of aluminum.
In the above process, the evaporation speed of the organic material is maintained
Second, aluminum maintenance
A vapor deposition rate per second, and a degree of vacuum maintained at 1X 10 during vapor deposition -7 ～5×10 -8 And (7) supporting.
< Experimental examples 2 to 16>
An organic light-emitting device was produced in the same manner as in experimental example 1, except that in experimental example 1, the compounds described in table 1 below were used instead of compound 1 of example 1.
< comparative Experimental examples 1 to 3>
An organic light-emitting device was produced in the same manner as in experimental example 1, except that in experimental example 1, compounds described in table 1 below were used instead of compound 1. The compounds of CE1 of table 1 below are shown below.
In the above experimental examples and comparative experimental examples, the organic light emitting device was operated at 10mA/cm 2 The voltage and efficiency were measured at a current density of 50mA/cm 2 The lifetime was measured at the current density of (2), and the results are shown in table 1 below. In this case, LT95 represents a time of 95% with respect to the initial luminance.
[ Table 1]
As shown in table 1, it was confirmed that when the compound of the present invention was used as a light-emitting layer material, the efficiency and lifetime exhibited superior characteristics as compared with the comparative experimental examples. It was shown that the electron stability increased with substitution of triazine and carbazolyl groups on the dibenzofuranyl group as a core substituent. In particular, when one or more deuterium groups are substituted on the additional aryl group and the carbazolyl group, excellent characteristics are exhibited in terms of lifetime increase. It also shows increased electronic stability.
[ description of symbols ]
1: substrate 2: anode
3: hole transport layer 4: luminescent layer
5: electron injection and transport layer 6: cathode electrode
7: hole injection layer 8: electron inhibiting layer
9: a hole blocking layer.
Claims (10)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the reaction mixture is,
x are each independently N or CH, and 2 or more of the X are N,
y is O or S, and Y is O or S,
L 1 is a direct bond, or a substituted or unsubstituted C 6-60 An arylene group, a heterocyclic group, or a heterocyclic group,
L 2 is a direct bond, or a substituted or unsubstituted C 6-60 An arylene group, a cyclic or cyclic alkylene group,
Ar 1 and Ar 2 Each independently 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 6-60 (ii) a heteroaryl group, wherein,
R 1 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 6-60 (ii) a heteroaryl group, wherein,
R 2 each independently of the other is hydrogen or deuterium,
but Ar is 1 、Ar 2 And R 1 Is substituted with more than one deuterium, or R 2 Is deuterium.
2. The compound of claim 1, wherein L 1 Is a direct bond, phenylene, biphenylene or naphthylene.
3. The compound of claim 1, wherein L 2 Is a direct bond or a phenylene group.
4. The compound of claim 1, wherein Ar 1 And Ar 2 Each independently of the others is phenyl, biphenyl, naphthyl, naphthylphenyl, phenanthryl, carbazol-9-yl, 9-phenyl-9H-carbazolyl, dibenzofuranyl or dibenzothiophenyl,
ar is 1 And Ar 2 Unsubstituted or substituted with more than one deuterium.
5. The compound of claim 1, wherein R 1 Is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzofuranyl or dibenzothiophenyl,
said R is 1 Unsubstituted, or substituted with more than one deuterium.
6. The compound of claim 1, wherein X is all N.
7. The compound of claim 1, wherein Y is O.
8. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
9. 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 8.
10. The organic light-emitting device according to claim 9, wherein the organic layer containing the compound is a light-emitting layer.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2020-0097603 | 2020-08-04 | ||
| KR20200097603 | 2020-08-04 | ||
| KR10-2021-0101875 | 2021-08-03 | ||
| KR1020210101875A KR102591468B1 (en) | 2020-08-04 | 2021-08-03 | Novel compound and organic light emitting device comprising the same |
| PCT/KR2021/010241 WO2022031013A1 (en) | 2020-08-04 | 2021-08-04 | Novel compound and organic light-emitting device comprising same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115551852A true CN115551852A (en) | 2022-12-30 |
Family
ID=80117545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180034264.7A Pending CN115551852A (en) | 2020-08-04 | 2021-08-04 | Novel compound and organic light emitting device comprising same |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN115551852A (en) |
| WO (1) | WO2022031013A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4074706A1 (en) * | 2021-04-16 | 2022-10-19 | LG Display Co., Ltd. | Deuterated heterocyclic compound, organic light emitting device including the same and composition for organic layer of organic light emitting device |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5831654B1 (en) * | 2015-02-13 | 2015-12-09 | コニカミノルタ株式会社 | Aromatic heterocycle derivative, organic electroluminescence device using the same, illumination device and display device |
| KR101885899B1 (en) * | 2016-11-07 | 2018-08-06 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| KR20180108425A (en) * | 2017-03-24 | 2018-10-04 | 희성소재 (주) | Heterocyclic compound and organic light emitting device comprising the same |
| KR102038031B1 (en) * | 2017-09-15 | 2019-10-30 | 엘티소재주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| KR102231197B1 (en) * | 2018-07-27 | 2021-03-23 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| US20220306616A1 (en) * | 2019-12-20 | 2022-09-29 | Lg Chem, Ltd. | Novel compound and organic light emitting device comprising the same |
-
2021
- 2021-08-04 WO PCT/KR2021/010241 patent/WO2022031013A1/en active Application Filing
- 2021-08-04 CN CN202180034264.7A patent/CN115551852A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2022031013A1 (en) | 2022-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112673005A (en) | Novel compound and organic light emitting device comprising same | |
| CN110869372B (en) | Compound and organic light-emitting element using same | |
| CN108884086B (en) | Heterocyclic compound and organic light-emitting element using same | |
| EP3730488B1 (en) | Novel heterocyclic compound and organic light emitting device using same | |
| CN113423705A (en) | Novel compound and organic light emitting device using the same | |
| CN112771037A (en) | Novel compound and organic light emitting device comprising same | |
| CN113423706A (en) | Novel compound and organic light emitting device comprising same | |
| KR20200085232A (en) | Novel compound and organic light emitting device comprising the same | |
| CN115461339A (en) | Novel compound and organic light emitting device comprising same | |
| CN112334472B (en) | Novel compound and organic light emitting device comprising the same | |
| CN113795488A (en) | Novel compound and organic light emitting device comprising same | |
| CN113227085A (en) | Novel compound and organic light emitting device comprising same | |
| CN113039183A (en) | Novel compound and organic light emitting device comprising same | |
| CN113272307A (en) | Novel compound and organic light emitting device using the same | |
| CN112912375A (en) | Novel compound and organic light emitting device comprising same | |
| CN112703192A (en) | Novel compound and organic light emitting device comprising same | |
| CN111328329A (en) | Novel heterocyclic compound and organic light emitting device using the same | |
| KR102591470B1 (en) | Novel compound and organic light emitting device comprising the same | |
| CN113454078B (en) | Novel heterocyclic compound and organic light-emitting device comprising same | |
| CN115551852A (en) | Novel compound and organic light emitting device comprising same | |
| CN115551853A (en) | Novel compound and organic light emitting device comprising same | |
| CN115605473A (en) | Novel compound and organic light emitting device comprising the same | |
| CN115551854A (en) | Novel compound and organic light emitting device comprising same | |
| KR20220017368A (en) | Novel compound and organic light emitting device comprising the same | |
| CN115867555A (en) | Novel compound and organic light emitting device comprising 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 |