CN111225904A - Heterocyclic compound and organic light-emitting device comprising same - Google Patents
Heterocyclic compound and organic light-emitting device comprising same Download PDFInfo
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- CN111225904A CN111225904A CN201980005092.3A CN201980005092A CN111225904A CN 111225904 A CN111225904 A CN 111225904A CN 201980005092 A CN201980005092 A CN 201980005092A CN 111225904 A CN111225904 A CN 111225904A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 33
- 239000000126 substance Substances 0.000 claims abstract description 74
- 239000010410 layer Substances 0.000 claims description 124
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 239000012044 organic layer Substances 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000002560 nitrile group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 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 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- -1 1-methylpentyl group Chemical group 0.000 description 68
- 150000001875 compounds Chemical class 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- 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 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 230000000903 blocking effect Effects 0.000 description 24
- 239000000758 substrate Substances 0.000 description 23
- 238000004519 manufacturing process Methods 0.000 description 19
- 230000032258 transport Effects 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 11
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000001624 naphthyl group Chemical group 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 125000005561 phenanthryl group Chemical group 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 125000005580 triphenylene group Chemical group 0.000 description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 7
- 125000006267 biphenyl group Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 125000005264 aryl amine group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 125000005577 anthracene group Chemical group 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 238000005240 physical vapour deposition Methods 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000004653 anthracenylene group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 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
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005566 electron beam evaporation Methods 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
- 125000005842 heteroatom Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000642 polymer Polymers 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
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 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 1
- 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 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- 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 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
- 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
- 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
- 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
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 229910052772 Samarium 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
- 229910052769 Ytterbium Inorganic materials 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
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 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
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- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
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- 229940126214 compound 3 Drugs 0.000 description 1
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- 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
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
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- 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
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 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
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 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
- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 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
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- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 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
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- 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
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- 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
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- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition 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
- 238000007740 vapor deposition Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
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Abstract
The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present specification claims priority from korean patent application No. 10-2018-0024543, which was filed on 28.2.2018 from the korean patent office, the entire contents of which are incorporated herein.
The present specification relates to a heterocyclic compound and an organic light-emitting device formed using the heterocyclic compound.
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 generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed 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, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.
There is a continuing demand for the development of new materials for organic light emitting devices as described above.
Disclosure of Invention
Technical subject
The present specification provides heterocyclic compounds and organic light-emitting devices comprising the same.
Means for solving the problems
According to one embodiment of the present specification, there is provided a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-described chemical formula 1,
q is
X1 to X3, which are identical to or different from one another, are each independently N or CR,
any one or more of X1 to X3 is N,
r and R1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring,
l1 is a direct bond or a substituted or unsubstituted arylene group,
a1 and A2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl,
a and b are each an integer of 0 to 5, and when a and b are each 2 or more, R1 may be the same or different from each other, R2 may be the same or different from each other,
c is an integer of 0 to 3, and when c is 2 or more, R3 may be the same or different from each other,
d is an integer of 0 to 8, and when d is 2 or more, R4 may be the same or different from each other.
In addition, the present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the heterocyclic compound.
Effects of the invention
The heterocyclic compound according to one embodiment of the present specification can be used as a material for an organic layer of an organic light-emitting device, and by using the compound, improvement in efficiency, low driving voltage, and/or improvement in lifetime characteristics can be achieved in the organic light-emitting device.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device according to an embodiment of the present specification.
[ description of symbols ]
1: substrate
2: a first electrode
3: organic material layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electron blocking layer
8: luminescent layer
9: hole blocking layer
10: electron injection and transport layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides heterocyclic compounds represented by the above chemical formula 1.
The present specification provides compounds characterized by the incorporation of a N-containing heterocycle with a fused ring core.
In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.
In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or substituted with substituents formed by connecting 2 or more substituents among the above-exemplified substituents, or without any substituent. For example, the "substituent in which 2 or more substituents are bonded" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and 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 30. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethylpropyl group, 1-dimethyl-propyl group, isohexyl group, isohex, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a2, 3-dimethylcyclohexyl group, a3, 4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
In the present specification, the silyl group is a substituent containing Si and directly bonded to the Si atom as a radical, and is represented by-SiR104R105R106Is represented by R104To R106The substituent group may be a substituent group composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. 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, specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group and the like, but the phosphine oxide group is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be a monocyclic ring or polycyclic ring.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a perylene group,
and a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like. But is not limited thereto.
In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more of the above-mentioned aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group.
In the present specification, the heteroaryl group may contain one or more heteroatoms other than carbon atoms, and specifically, the heteroatom may contain one or more atoms selected from O, N, Se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, arylene is the same as defined for aryl, except that it has a valence of 2.
In the present specification, heteroarylene group is defined as the same as heteroaryl group, except that it has a valence of 2.
In the present specification, Q is any one of the following chemical formulae 1-1 to 1-3.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
In the above chemical formulas 1-1 to 1-3, the dotted line is a site binding to the nucleus of the above chemical formula 1, and the above R4 and d are the same as defined in the above chemical formula 1.
In the present specification, the above chemical formula 1 is represented by the following chemical formula 2.
[ chemical formula 2]
In the above chemical formula 2, the above R1 to R4, X1 to X3, a1, a2, L1, and a to d are the same as defined in the above chemical formula 1.
In the present specification, the above-mentioned X1 to X3 are N.
In the present specification, X1 and X2 are N, and X3 is CR.
In the present specification, X1 and X3 are N, and X2 is CR.
In the present specification, X2 and X3 are N, and X1 is CR.
In the present specification, L1 represents a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In the present specification, L1 represents an arylene group having 6 to 30 carbon atoms which is directly bonded to or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
In the present specification, L1 is a monocyclic arylene group having 6 to 30 carbon atoms which is directly bonded to or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
In the present specification, L1 represents a polycyclic arylene group having 6 to 30 carbon atoms which is directly bonded to or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
In the present specification, the above L1 represents a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a quaterphenylene group, a naphthylene group, a phenanthrylene group, a dimethylfluorenylene group, a pyrenylene group, a triphenylene group or an anthracenylene group.
In the present specification, L1 represents a direct bond, a phenylene group, a biphenylene group, a naphthylene group or an anthracenylene group.
In the present specification, the L1 represents any one of the following substituents.
In the present specification, L1 is a direct bond.
In the present specification, the above-mentioned L1 is a phenylene group.
In the present specification, L1 is a biphenylene group.
In the present specification, the above-mentioned L1 is a naphthylene group.
In the present specification, the L1 is an anthracenylene group.
According to an embodiment of the present specification, the above R1 to R4 and R, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, the above R1 to R4 and R, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring.
According to an embodiment of the present disclosure, R1 through R4 and R are hydrogen.
According to an embodiment of the present disclosure, a1 and a2 are the same as each other and each is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, a1 and a2 are the same as each other and are substituted or unsubstituted aryl groups.
According to an embodiment of the present disclosure, a1 and a2 are the same as each other and are substituted or unsubstituted heteroaryl groups containing N, O or S.
According to an embodiment of the present disclosure, a1 and a2 are different from each other and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, a1 and a2 are different from each other and each independently is a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, a1 and a2 are different from each other and each independently a substituted or unsubstituted heteroaryl group including at least one of N, O and S.
According to an embodiment of the present disclosure, a1 is a substituted or unsubstituted aryl group, and a2 is a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present disclosure, a2 is a substituted or unsubstituted aryl group, and a1 is a substituted or unsubstituted heteroaryl group.
According to one embodiment of the present specification, a1 and a2 which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S, respectively,
the above substituted or unsubstituted aryl group having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S may be substituted or unsubstituted with deuterium, a nitrile group, a halogen group, an alkyl group, an aryl group, or a heteroaryl group including N, O and S.
According to one embodiment of the present specification, a1 and a2 are the same and each represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S or more,
the above substituted or unsubstituted aryl group having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S may be substituted or unsubstituted with deuterium, a nitrile group, a halogen group, an alkyl group, an aryl group, or a heteroaryl group including N, O and S.
According to one embodiment of the present specification, a1 and a2 are, different from each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S or more,
the above substituted or unsubstituted aryl group having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S may be substituted or unsubstituted with deuterium, a nitrile group, a halogen group, an alkyl group, an aryl group, or a heteroaryl group including N, O and S.
In the present specification, A1 and A2, which are the same as each other, may be selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms and containing N, O and S or more,
the above-mentioned substituted or unsubstituted aryl group having 6 to 30 carbon atoms and the substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S may be substituted or unsubstituted with deuterium, a nitrile group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms including N, O and S.
In the present specification, A1 and A2, which are the same as each other, may be selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms and containing N, O and S or more,
the substituted or unsubstituted aryl group having 6 to 30 carbon atoms and the substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms including N, O and S are each a phenyl group substituted or unsubstituted with deuterium, a nitrile group, a methyl group, a tert-butyl group, a phenyl group, a trimethylsilyl group, a dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group, an anthracenyl group, a naphthyl group, a triphenylenyl group or a dimethylfluorenyl group; a biphenyl group substituted or unsubstituted with a nitrile group; a terphenyl group; a naphthyl group; an anthracene group; phenanthryl; a triphenylene group; fluorenyl substituted or unsubstituted with methyl or phenyl; spirobifluorenyl; a pyridyl group; carbazolyl substituted or unsubstituted with phenyl; dibenzofuranyl substituted or unsubstituted with phenyl; dibenzothienyl substituted or unsubstituted with phenyl; a benzonaphthofuranyl group; or benzonaphthothienyl.
In the present specification, the above-mentioned a1 and a2, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, a methyl group, a nitrile group, a tert-butyl group, a phenyl group, a trimethylsilyl group, a dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group, an anthracenyl group, a naphthyl group, a triphenylene group or a dimethylfluorenyl group; a biphenyl group substituted or unsubstituted with a nitrile group; a terphenyl group; a naphthyl group; an anthracene group; phenanthryl; a triphenylene group; a dimethyl fluorenyl group; a diphenylfluorenyl group; spirobifluorenyl; a pyridyl group; a pyrimidinyl group; a triazine group; carbazolyl substituted or unsubstituted with phenyl; dibenzofuranyl substituted or unsubstituted with phenyl; dibenzothienyl substituted or unsubstituted with phenyl; a benzonaphthofuranyl group; or benzonaphthothienyl.
In the present specification, a1 and a2 are the same as each other and each represents a phenyl group substituted or unsubstituted with deuterium, a methyl group, a nitrile group, a tert-butyl group, a phenyl group, a trimethylsilyl group, a dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group, an anthracenyl group, a naphthyl group, a triphenylene group or a dimethylfluorenyl group; a biphenyl group substituted or unsubstituted with a nitrile group; a terphenyl group; a naphthyl group; an anthracene group; phenanthryl; a triphenylene group; a dimethyl fluorenyl group; a diphenylfluorenyl group; spirobifluorenyl; a pyridyl group; a pyrimidinyl group; a triazine group; carbazolyl substituted or unsubstituted with phenyl; dibenzofuranyl substituted or unsubstituted with phenyl; dibenzothienyl substituted or unsubstituted with phenyl; a benzofuranyl group; or a benzonaphthylthienyl group.
In the present specification, the above-mentioned a1 and a2 are different from each other and each independently represents a phenyl group substituted or unsubstituted with deuterium, a methyl group, a nitrile group, a tert-butyl group, a phenyl group, a trimethylsilyl group, a dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group, an anthracenyl group, a naphthyl group, a triphenylene group or a dimethylfluorenyl group; a biphenyl group substituted or unsubstituted with a nitrile group; a terphenyl group; a naphthyl group; an anthracene group; phenanthryl; a triphenylene group; a dimethyl fluorenyl group; a diphenylfluorenyl group; spirobifluorenyl; a pyridyl group; a pyrimidinyl group; a triazine group; carbazolyl substituted or unsubstituted with phenyl; dibenzofuranyl substituted or unsubstituted with phenyl; dibenzothienyl substituted or unsubstituted with phenyl; a benzonaphthofuranyl group; or benzonaphthothienyl.
In the present specification, the above-mentioned a1 and a2, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, a methyl group, a tert-butyl group, a phenyl group, a trimethylsilyl group, or a nitrile group; a biphenyl group substituted or unsubstituted with a nitrile group; a naphthyl group; phenanthryl; a dimethyl fluorenyl group; a diphenylfluorenyl group; a pyridyl group; carbazolyl substituted or unsubstituted with phenyl; dibenzofuranyl substituted or unsubstituted with phenyl; or dibenzothienyl substituted or unsubstituted with phenyl.
In the present specification, the above-mentioned a1 and a2, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, a methyl group, a tert-butyl group, a phenyl group, a trimethylsilyl group, or a nitrile group; a biphenyl group substituted or unsubstituted with a nitrile group; a naphthyl group; fluorenyl substituted or unsubstituted with methyl or phenyl; a pyridyl group; carbazolyl substituted or unsubstituted with phenyl; dibenzofuranyl substituted or unsubstituted with phenyl; or dibenzothienyl substituted or unsubstituted with phenyl; phenanthryl; or a terphenyl group.
In the present specification, a1 and a2 may be the same as or different from each other, and each independently may be any one of the following substituents.
Among the above-mentioned substituents, the above-mentioned,
is the site of attachment to the nucleus.
According to another embodiment of the present specification, the heterocyclic compound of the above chemical formula 1 may be represented by any one selected from the following structural formulae.
In addition, an organic electroluminescent device according to the present invention is characterized by comprising: the organic light emitting device includes a first electrode, a second electrode disposed to face the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers include a heterocyclic compound represented by the chemical formula 1.
The organic light-emitting device of the present invention can be produced by a method and a material for producing a general organic light-emitting device, in addition to forming one or more organic layers using the above compound.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, 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 one or more layers of an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection, and one or more layers of the layers may include the compound.
The organic light-emitting device of the present invention includes a substrate and a first electrode, an organic material layer, and a second electrode stacked in this order on the substrate.
The organic light-emitting device includes a substrate, and a first electrode, a light-emitting layer, a hole-blocking layer, and a second electrode stacked in this order on the substrate.
The organic light-emitting device includes a substrate, and a first electrode, a hole transport layer, a light-emitting layer, a hole blocking layer, and a second electrode stacked in this order on the substrate.
The organic light emitting device of the present invention includes a first electrode, a light emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode stacked in this order on a substrate.
The organic light-emitting device includes a substrate, and a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode stacked in this order on the substrate.
The organic light-emitting device of the present invention includes a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode stacked in this order on a substrate.
Fig. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
Fig. 2 illustrates a structure of an organic light emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked on a substrate 1.
The organic light emitting device is illustrated in fig. 1 and 2, but is not limited thereto.
In one embodiment of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound of chemical formula 1.
In one embodiment of the present invention, the organic layer may include a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer may include the heterocyclic compound of chemical formula 1.
In one embodiment of the present invention, the organic layer may include an electron injection layer, an electron transport layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, or the hole blocking layer may include the heterocyclic compound of chemical formula 1.
In one embodiment of the present invention, the organic layer may include a hole blocking layer, and the hole blocking layer may include a heterocyclic compound of the chemical formula 1.
For example, the organic light emitting device according to the present invention may be manufactured as follows: the organic el 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) 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 and an organic layer including the heterocyclic compound of the above chemical formula 1 on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order.
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 that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO: al or SnO2: 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 (PEDT), 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 LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injecting substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and conductive polymers of polymeric compounds.
The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer them to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric 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 include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivative includes anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene compounds, and the like, and the heterocyclic ring-containing compound includes heterocyclic compounds, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
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.
The organic light-emitting device of the present specification can be manufactured by using a material and a method known in the art, except that one or more layers of the organic layer are formed using the heterocyclic compound.
For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the following production can be performed: 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 Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (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, an organic light-emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order.
The present specification also provides a method for manufacturing an organic light-emitting device using the heterocyclic compound.
Specifically, an embodiment of the present specification includes the steps of: preparing a substrate; forming a cathode or an anode on the substrate; forming one or more organic layers on the cathode or the anode; and a step of forming an anode or a cathode on the organic layers, wherein at least one of the organic layers is formed using the heterocyclic compound.
As the dopant material, there are an aromatic heterocyclic compound, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic heterocyclic compound is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, perylene, and the like having an arylamine group,
Diindenopyrene and the like, as the styrylamine compound, a compound having at least one arylvinyl group substituted on a substituted or unsubstituted arylamine, selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylaminoOne or two or more substituents of (a) or (b) are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons well from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: the organic light-emitting device has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and has excellent thin-film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
According to an embodiment of the present specification, the heterocyclic compound of chemical formula 1 may be produced according to the following reaction formula, but is not limited thereto. In the following reaction schemes, with respect to the kind and number of substituents, those skilled in the art can synthesize various intermediates by appropriately selecting known starting materials. The kind of reaction and the reaction conditions may be those known in the art.
In the above formulae, X1 to X3, L, A1 and a2 are the same as defined in chemical formula 1.
The method for producing the heterocyclic compound of chemical formula 1 and the production of the organic light-emitting device using the same are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
The heterocyclic compound of the above chemical formula 1 described in the present specification can be produced in its entirety by appropriately combining the production formula described in the examples of the present specification and the intermediate described above based on general technical common knowledge.
Production example 1
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound A (7.50g, 15.12mmol) and Compound a1(5.87g, 16.63mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), stirring was performed for 3 hours under heating. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220mL of ethyl acetate, thereby producing compound 1(7.56g, 69%).
MS[M+H]+＝726
Production example 2
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound A (7.50g, 15.12mmol) and Compound a2(5.87g, 16.63mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), stirring was performed for 3 hours under heating. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220mL of ethyl acetate, thereby producing compound 2(6.82g, 62%).
MS[M+H]+＝726
Production example 3
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound A (7.50g, 15.12mmol) and Compound a3(5.87g, 16.63mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), stirring was performed for 3 hours under heating. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220mL of ethyl acetate, thereby producing compound 3(6.28g, 57%).
MS[M+H]+＝725
Production example 4
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound A (7.50g, 15.12mmol) and Compound a4(7.14g, 16.63mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), stirring was performed under heating for 3 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220mL of tetrahydrofuran, thereby producing compound 4(9.54g, 79%).
MS[M+H]+＝802
Production example 5
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A-1(10.01g, 18.44mmol) and Compound a5(5.50g, 16.03mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.56g, 0.48mmol), the mixture was stirred under heating for 3 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310mL of ethyl acetate, thereby producing compound 5(8.82g, 76%).
MS[M+H]+＝726
Production example 6
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound A-1(9.33g, 17.19mmol) and Compound a6(5.50g, 14.95mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol) was added, and the mixture was stirred under heating for 3 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210mL of ethyl acetate, thereby producing compound 6(5.49g, 49%).
MS[M+H]+＝751
Production example 7
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound A-1(9.33g, 17.19mmol) and Compound a7(5.50g, 14.95mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol) was added, and the mixture was stirred under heating for 3 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210mL of ethyl acetate, thereby producing compound 7(5.49g, 49%).
MS[M+H]+＝751
Production example 8
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound B-1(10.01g, 18.44mmol) and Compound a5(5.50g, 16.03mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.56g, 0.48mmol), the mixture was stirred under heating for 3 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230mL of ethyl acetate, thereby producing compound 8(7.12g, 61%).
MS[M+H]+＝726
Production example 9
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound B (7.50g, 15.12mmol) and Compound a1(6.31g, 17.39mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), the mixture was stirred under heating for 5 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230mL of ethyl acetate, thereby producing compound 9(7.12g, 61%).
MS[M+H]+＝726
Production example 10
In a 500mL round-bottom flask under nitrogen, after completely dissolving Compound B (7.50g, 15.12mmol) and Compound a3(5.87g, 16.63mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.52g, 0.45mmol), stirring was performed for 3 hours under heating. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220mL of ethyl acetate, thereby producing compound 10(5.37g, 49%).
MS[M+H]+＝725
Production example 11
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A-1(13.14g, 24.16mmol) and Compound a6(7.50g, 21.01mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.73g, 0.63mmol), stirring was carried out for 3 hours under heating. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250mL of ethyl acetate, thereby producing compound 11(10.44g, 68%).
MS[M+H]+＝726
Production example 12
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A-1(12.58g, 23.12mmol) and Compound a7(7.50g, 20.11mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.70g, 0.60mmol), the mixture was stirred under heating for 3 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250mL of ethyl acetate, thereby producing compound 12(9.36g, 62%).
MS[M+H]+＝756
Production example 13
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound B-1(14.80g, 27.21mmol) and Compound a8(7.50g, 23.66mmol) in 240mL tetrahydrofuran, 2M aqueous potassium carbonate (120mL) was added, and after adding tetrakis (triphenylphosphine) palladium (0.82g, 0.71mmol), stirring was carried out for 3 hours under heating. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230mL of ethyl acetate, thereby producing compound 13(10.75g, 65%).
MS[M+H]+＝700
Examples 1 to 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, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. Further, the substrate is subjected to oxygen plasmaAfter 5 minutes of cleaning, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared as an anode, the compound of the following compound HI1 and the compound of the following compound HI2 were added in such a ratio that the molar ratio was 98:2 (molar ratio)
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, a compound represented by the following chemical formula HT1
Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, a compound of EB1 was formed in a film thickness
Vacuum evaporation is performed to form an electron blocking layer. Next, on the above electron blocking layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were mixed at a weight ratio of 25:1 and in a film thickness
Vacuum evaporation is performed to form a light emitting layer. On the light-emitting layer, compound 1 is formed in a film thickness
The hole blocking layer is formed by vacuum evaporation. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form a hole blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the thickness of (3) is evaporated to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And (4) supporting to manufacture the organic light-emitting device.
Examples 1-2 to examples 1-13
An organic light-emitting device was produced in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of compound 1.
Comparative examples 1-1 to 1-8
An organic light-emitting device was produced in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of compound 1. The compounds of HB1 to HB8 used in table 1 below are as follows.
Experimental example 1
The results of measuring the voltage, efficiency, color coordinates and lifetime when a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples are shown in table 1 below. T95 represents the time required for the luminance to decrease from the initial luminance (1600nit) to 95%.
[ Table 1]
Observing the above table 1, the organic light emitting device using the compound of the present invention as a hole blocking layer shows excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
The present invention shows low voltage, high efficiency and long life characteristics as compared with organic light emitting devices manufactured using the compound of comparative example 1-1 in which methyl groups are substituted at the 9 and 10 positions of the fluorene nucleus and the compounds of comparative examples 1-2 to 1-4 in which triazine and pyridine are bonded to the 2,3 and 4 positions of the benzofluorene nucleus as hole blocking layers.
In contrast to comparative examples 1 to 5, in which Q is a phenanthryl group, compounds in which the moiety corresponding to Q is benzene are used. Comparative examples 1 to 6 and comparative examples 1 to 7 differ from the present invention in that a compound having a methyl group substituted at the 9-position of the fluorene nucleus is used. Comparative example 8 uses a compound having only an aryl group substituted on the nucleus.
The present invention also exhibits low voltage, high efficiency, and long life when compared to comparative examples 1-5 to 1-8.
As shown in the results of table 1, it was confirmed that the compound according to the present invention is excellent in hole blocking ability and thus can be suitably used in an organic light-emitting device.
The preferred embodiment (hole blocking layer) of the present invention has been described above, but the present invention is not limited thereto, and may be modified into various forms within the scope of the claims of the present invention and the detailed description of the present invention, and the present invention also falls within the scope of the present invention.
Claims (8)
1. A heterocyclic compound represented by the following chemical formula 1:
chemical formula 1
Wherein in the chemical formula 1,
q is
X1 to X3, which are identical to or different from one another, are each independently N or CR,
any one or more of X1 to X3 is N,
r and R1 to R4, which are the same or different from each other, are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring,
l1 is a direct bond or a substituted or unsubstituted arylene group,
a1 and A2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl,
a and b are each an integer of 0 to 5, and when a and b are each 2 or more, R1 are the same or different from each other, R2 are the same or different from each other,
c is an integer of 0 to 3, and when c is 2 or more, R3 may be the same or different from each other,
d is an integer of 0 to 8, and when d is 2 or more, R4 may be the same or different from each other.
2. The heterocyclic compound according to claim 1, wherein Q is any one of the following chemical formulae 1-1 to 1-3:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1 to 3
In the chemical formulas 1-1 to 1-3, the dotted line is a site bound to the nucleus of the chemical formula 1, and the R4 and d are the same as defined in the chemical formula 1.
3. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2:
chemical formula 2
In the chemical formula 2, the R1 to R4, X1 to X3, a1, a2, L1, and a to d are the same as defined in the chemical formula 1.
4. The heterocyclic compound according to claim 1, wherein the L1 is an arylene group having 6 to 30 carbon atoms which is directly bonded, or substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
5. The heterocyclic compound according to claim 1, wherein a1 and a2, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group containing 3 to 20 carbon atoms or more of N, O and S, which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
6. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is any one selected from the following structural formulae:
7. an organic light emitting device comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the heterocyclic compound according to any one of claims 1 to 6.
8. The organic light-emitting device according to claim 7, wherein the organic layer comprises a hole-blocking layer containing the heterocyclic compound.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2011081403A2 (en) * | 2009-12-30 | 2011-07-07 | 주식회사 두산 | Organic luminescent compound and an organic electroluminescent element comprising the same |
| KR20120066390A (en) * | 2010-12-14 | 2012-06-22 | 에스에프씨 주식회사 | Anthracene deriva tives and organic light-emitting diode including the same |
| JP2015216245A (en) * | 2014-05-12 | 2015-12-03 | Tdk株式会社 | Compound for organic electroluminescent element and organic electroluminescent element using the same |
| JP2016150920A (en) * | 2015-02-18 | 2016-08-22 | Tdk株式会社 | Compound for organic electroluminescent element and organic electroluminescent element using the same |
| CN106132937A (en) * | 2014-04-04 | 2016-11-16 | 株式会社Lg化学 | Heterocyclic compound and the organic luminescent device comprising it |
| KR20170056431A (en) * | 2015-11-13 | 2017-05-23 | 에스에프씨 주식회사 | Novel heterocyclic compound and organic light-emitting diode including the same |
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| KR20120066390A (en) * | 2010-12-14 | 2012-06-22 | 에스에프씨 주식회사 | Anthracene deriva tives and organic light-emitting diode including the same |
| CN106132937A (en) * | 2014-04-04 | 2016-11-16 | 株式会社Lg化学 | Heterocyclic compound and the organic luminescent device comprising it |
| JP2015216245A (en) * | 2014-05-12 | 2015-12-03 | Tdk株式会社 | Compound for organic electroluminescent element and organic electroluminescent element using the same |
| JP2016150920A (en) * | 2015-02-18 | 2016-08-22 | Tdk株式会社 | Compound for organic electroluminescent element and organic electroluminescent element using the same |
| KR20170056431A (en) * | 2015-11-13 | 2017-05-23 | 에스에프씨 주식회사 | Novel heterocyclic compound and organic light-emitting diode including the same |
Cited By (1)
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|---|---|---|---|---|
| WO2022205090A1 (en) * | 2021-03-31 | 2022-10-06 | 京东方科技集团股份有限公司 | Display substrate and display apparatus |
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