CN117580832A - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
- Publication number
- CN117580832A CN117580832A CN202380012553.6A CN202380012553A CN117580832A CN 117580832 A CN117580832 A CN 117580832A CN 202380012553 A CN202380012553 A CN 202380012553A CN 117580832 A CN117580832 A CN 117580832A
- Authority
- CN
- China
- Prior art keywords
- unsubstituted
- substituted
- group
- chemical formula
- compound
- 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 102
- 239000000126 substance Substances 0.000 claims abstract description 119
- 239000010410 layer Substances 0.000 claims description 202
- 238000002347 injection Methods 0.000 claims description 76
- 239000007924 injection Substances 0.000 claims description 76
- 125000003118 aryl group Chemical group 0.000 claims description 72
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- -1 aryl Azole Chemical compound 0.000 claims description 41
- 239000012044 organic layer Substances 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- 229910052805 deuterium Inorganic materials 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000000732 arylene group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000004306 triazinyl group Chemical group 0.000 claims description 13
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000004867 thiadiazoles Chemical group 0.000 claims description 2
- 230000005525 hole transport Effects 0.000 description 37
- 238000004519 manufacturing process Methods 0.000 description 34
- 239000000463 material Substances 0.000 description 32
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000000034 method Methods 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 125000001624 naphthyl group Chemical group 0.000 description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 125000002950 monocyclic group Chemical group 0.000 description 20
- 125000003367 polycyclic group Chemical group 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 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 16
- 235000010290 biphenyl Nutrition 0.000 description 15
- 239000004305 biphenyl Substances 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 14
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 125000006267 biphenyl group Chemical group 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 11
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 125000001544 thienyl group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000002541 furyl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000001629 suppression Effects 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VBQVHWHWZOUENI-UHFFFAOYSA-N 1-phenyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 VBQVHWHWZOUENI-UHFFFAOYSA-N 0.000 description 3
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 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 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000007650 screen-printing Methods 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
- 238000004528 spin coating Methods 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- WTAPZWXVSZMMDG-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WTAPZWXVSZMMDG-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
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PJRJXFPRMUZBHQ-UHFFFAOYSA-N [Ir].C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 Chemical compound [Ir].C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 PJRJXFPRMUZBHQ-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes 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
- 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
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 150000001616 biphenylenes Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 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
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic 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
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 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
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005842 heteroatom 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
- 150000002460 imidazoles Chemical class 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 239000011133 lead Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- ANYCDYKKVZQRMR-UHFFFAOYSA-N lithium;quinoline Chemical group [Li].N1=CC=CC2=CC=CC=C21 ANYCDYKKVZQRMR-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 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
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-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
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 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
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010345 tape casting Methods 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
- 238000010023 transfer printing Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- 125000006617 triphenylamine group Chemical group 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic 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
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present application claims priority from korean patent application No. 10-2022-0003739, filed to the korean patent office on 1 month 11 of 2022, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device including the same.
Background
In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor substance, and communication of holes and/or electrons between an electrode and the organic semiconductor substance is required. Organic light emitting devices can be broadly classified into the following two types according to the operation principle. The first is a light-emitting device in which an exciton (exiton) is formed in an organic layer by photons flowing into the device from an external light source, and the exciton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light-emitting device in which a voltage or a current is applied to 2 or more electrodes, holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes, and the injected electrons and holes operate.
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 and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons re-transition to a ground state. Such an organic light emitting device is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and the like.
Materials used as an organic layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material, such as a hole injecting material, a hole transporting material, an electron inhibiting substance, an electron transporting material, an electron injecting material, and the like, according to functions. Depending on the emission color, the luminescent materials are blue, green, red luminescent materials, and yellow and orange luminescent materials, which are required to achieve better natural colors.
In addition, for the purpose of an increase in color purity and an increase in luminous efficiency based on energy transfer, as a light emitting material, a host/dopant system may be used. The principle is that when a dopant having a smaller band gap and excellent light emission efficiency than a host mainly constituting the light emitting layer is mixed in a small amount in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength range of the dopant, light of a desired wavelength can be obtained according to the kind of the dopant to be used.
In order to fully develop the excellent characteristics of the organic light-emitting device, materials constituting the organic layer in the device, for example, hole injection materials, hole transport materials, light-emitting materials, electron-suppressing materials, electron transport materials, electron injection materials, and the like are stable and effective materials, and therefore development of new materials is continuously demanded.
Disclosure of Invention
Technical problem
The present specification describes compounds and organic light emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound of the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
l1 and L2 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
Ar1 is represented by the following chemical formula 2 or 3,
[ chemical formula 2]
[ chemical formula 3]
In the above-mentioned chemical formulas 2 and 3,
x1 is NR, O, S, CR R2, N linked to L1, or CR1 linked to L1,
x2 to X5 are identical to or different from each other and are each independently N, CR3 or C linked to L1,
however, X1 is NR, or at least one of X2 to X5 is N,
x1 is N linked to L1, or CR1 linked to L1, or
One of X2 to X5 is C linked to L1,
r and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may be combined with each other with adjacent substituents to form a substituted or unsubstituted ring,
y1 is O or S, and the total number of the components is equal to or less than zero,
y2 and Y3 are identical to or different from each other and are each independently N or CR4,
y4 to Y7 are identical to or different from each other and are each independently N, CR5 or C linked to L1,
at least one of Y4 to Y7 is C linked to L1,
r4 and R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may combine with each other with an adjacent substituent to form a substituted or unsubstituted ring,
ar2 is represented by the following chemical formula 4,
[ chemical formula 4]
In the above-mentioned chemical formula 4, a compound represented by formula 1,
x6 to X11 are identical to or different from each other and are each, independently of one another, N, CR6 or C combined with L2,
one of X6 to X11 is C bonded to L2, at least one of the others is N,
r6 is deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may combine with adjacent substituents with each other to form a substituted or unsubstituted ring.
In addition, according to an embodiment of the present invention, there is provided an organic light emitting device including: a first electrode, a second electrode provided opposite to 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 contains the compound.
Effects of the invention
The compound of the present invention can be used as a material of an organic layer of an organic light emitting device. In the case of manufacturing an organic light-emitting device by including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage, and long life characteristics can be obtained, and in the case of including the compound of the present invention in an electron transport layer of an organic light-emitting device, the effect of electron transfer increases due to high intramolecular polarization, and thus an organic light-emitting device having long life characteristics can be manufactured.
Drawings
Fig. 1 and 2 illustrate examples of an organic light emitting device according to the present invention.
[ description of the symbols ]
1: substrate board
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: light-emitting layer
8: electron injection and transport layers
Detailed Description
The present specification will be described in more detail below.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same 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, halogen group, cyano (-CN), silyl, boron group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, or substituted with 2 or more substituents bonded to the above exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).
In this specification, the silyl group may be substituted or unsubstituted with deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or the like. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group may be substituted or unsubstituted with deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and the like.
In the present specification, the amine group may be selected from the group consisting of-NH 2 The alkyl amine group, the N-alkylaryl amine group, the aryl amine group, the N-arylheteroaryl amine group, the N-alkylheteroaryl amine group and the heteroaryl amine group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, naphthylamino group, biphenylamino group, anthracenylamino group, 9-methylanthracenylamino group and diphenylamine group Examples of the amine group include, but are not limited to, a phenyl group, a xylylamine group, an N-phenyltolylamino group, a triphenylamine group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrenylfluolamino group, and an N-biphenylfluorenylamino group.
In the present specification, the N-alkylaryl amine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.
In the present specification, an N-arylheteroarylamino group means an amino group substituted with an aryl group and a heteroaryl group on N of the amino group.
In the present specification, an N-alkylheteroarylamino group means an amino group in which an alkyl group and a heteroaryl group are substituted on N of the amino group.
In the present specification, alkylamino, N-arylalkylamino, alkylthio Alkylsulfonyl->The alkyl group in the N-alkylheteroaryl amine group is the same as exemplified above for the alkyl group. Specifically, the alkylthio group includes a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like, and the alkylsulfonyl group includes a methanesulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and the like, but is not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, the heteroaryl group is a cyclic group containing 1 or more of N, O, P, S, si and Se as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, and carbazolyl.
In the present specification, the definition of arylene is the same as that of aryl described above except that arylene is a 2-valent group.
In the present specification, the heteroaryl group is defined as in the above heteroaryl group except that the heteroaryl group is a 2-valent group.
In this specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
In the above chemical formulas 1-1 to 1-6, the above L1, L2, ar1 and Ar2 are as defined in chemical formula 1.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other, and each is independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other, and each is independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group of 2 valences, a substituted or unsubstituted terphenyl group of 2 valences, a substituted or unsubstituted naphthyl group of 2 valences, a substituted or unsubstituted anthryl group of 2 valences, a substituted or unsubstituted phenanthryl group of 2 valences, a substituted or unsubstituted pyrenyl group of 2 valences, a substituted or unsubstituted carbazole group of 2 valences, a substituted or unsubstituted pyridinyl group of 2 valences, a substituted or unsubstituted pyrimidinyl group of 2 valences, a substituted or unsubstituted triazinyl group of 2 valences, a substituted or unsubstituted dibenzofuranyl group of 2 valences, a substituted or unsubstituted dibenzothiophenyl group of 2 valences, a substituted or unsubstituted thienyl group of 2 valences, a substituted or unsubstituted benzimidazolyl group of 2 valences, or a substituted or unsubstituted benzo group of 2 valences An azole group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted phenylene group, substituted or unsubstituted biphenyl group of 2 valences, substituted or unsubstituted naphthyl group of 2 valences, substituted or unsubstituted terphenyl group of 2 valences, substituted or unsubstituted carbazolyl group of 2 valences, substituted or unsubstituted pyridyl group of 2 valences, substituted or unsubstituted pyrimidinyl group of 2 valences, substituted or unsubstituted triazinyl group of 2 valences, substituted or unsubstituted dibenzothienyl group of 2 valences, substituted or unsubstituted furyl group of 2 valences, substituted or unsubstituted thienyl group of 2 valences, substituted or unsubstituted benzimidazolyl group of 2 valences, or substituted or unsubstituted benzo group of 2 valencesAn azole group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group having a valence of 2, a substituted or unsubstituted naphthyl group having a valence of 2, or a substituted or unsubstituted terphenyl group having a valence of 2.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted carbazolyl group of 2 valences, substituted or unsubstituted pyridinyl group of 2 valences, substituted or unsubstituted pyrimidinyl group of 2 valences, substituted or unsubstituted triazinyl group of 2 valences, substituted or unsubstituted dibenzofuranyl group of 2 valences, substituted or unsubstituted dibenzothienyl group of 2 valences, substituted or unsubstituted furanyl group of 2 valences, substituted or unsubstituted thienyl group of 2 valences, substituted or unsubstituted benzimidazolyl group of 2 valences, or substituted or unsubstituted benzo group of 2 valences An azole group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, substituted or unsubstituted 2-valent naphthyl, 2-valent anthryl, 2-valent phenanthryl, 2-valent pyrenyl, 2-valent carbazolyl, 2-valent pyridyl, 2-valent pyrimidinyl, 2-valent triazinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent furyl, 2-valent thienyl, 2-valent benzimidazolyl, or 2-valent benzoAn azole group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, phenylene, 2-valent biphenyl, 2-valent terphenyl, 2-valent carbazolyl, 2-valent pyridyl, 2-valent pyrimidinyl, 2-valent triazinyl, 2-valent dibenzofuranyl, 2-valent dibenzothienyl, 2-valent furyl, 2-valent thienylBenzimidazolyl, or 2-valent benzoAn azole group.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, a phenylene group, a biphenyl group having a valence of 2, a substituted or unsubstituted naphthyl group having a valence of 2, or a terphenyl group having a valence of 2.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a direct bond, a carbazolyl group of 2 valences, a pyridyl group of 2 valences, a pyrimidinyl group of 2 valences, a triazinyl group of 2 valences, a dibenzofuranyl group of 2 valences, a dibenzothienyl group of 2 valences, a furyl group of 2 valences, a thienyl group of 2 valences, a benzimidazolyl group of 2 valences, or a benzo group of 2 valencesAn azole group.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other, and each is independently a direct bond.
According to an embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and are each independently phenylene, substituted or unsubstituted naphthyl of 2 valency, biphenyl of 2 valency, or terphenyl of 2 valency.
According to an embodiment of the present specification, the above L1 and L2 are the same or different from each other and are each independently a carbazolyl group of 2 valences, a pyridinyl group of 2 valences, pyrimidinyl group of 2 valences, triazinyl group of 2 valences, dibenzofuranyl group of 2 valences, dibenzothienyl group of 2 valences, furyl group of 2 valences, thienyl group of 2 valences, benzimidazolyl group of 2 valences, or benzo group of 2 valencesAn azole group.
According to an embodiment of the present disclosure, the L1 and L2 are directly bonded.
According to an embodiment of the present specification, the above L1 and L2 are phenylene groups.
According to an embodiment of the present specification, L1 and L2 are naphthyl.
According to an embodiment of the present specification, L1 and L2 are biphenyl groups having a valence of 2.
According to one embodiment of the present specification, L1 and L2 are 2-valent terphenyl groups.
According to an embodiment of the present disclosure, L1 is a direct bond.
According to one embodiment of the present specification, L1 is phenylene.
According to one embodiment of the present specification, L1 is a 2-valent naphthyl group.
According to one embodiment of the present specification, L1 is a 2-valent biphenyl group.
According to one embodiment of the present specification, L1 is a 2-valent terphenyl group.
According to an embodiment of the present disclosure, the L2 is a direct bond.
According to an embodiment of the present specification, the L2 is phenylene.
According to one embodiment of the present specification, L2 is a 2-valent naphthyl group.
According to one embodiment of the present specification, L2 is a 2-valent biphenyl group.
According to one embodiment of the present specification, L2 is a 2-valent terphenyl group.
According to one embodiment of the present specification, X1 is NR.
According to one embodiment of the present specification, X1 is O.
According to one embodiment of the present disclosure, X1 is S.
According to one embodiment of the present disclosure, X1 is CR1R2.
According to one embodiment of the present specification, X1 is CR1 bonded to L1.
According to an embodiment of the present disclosure, X2 is N.
According to an embodiment of the present disclosure, X3 is N.
According to an embodiment of the present disclosure, X4 is N.
According to an embodiment of the present disclosure, X5 is N.
According to one embodiment of the present disclosure, X2 is CR3.
According to one embodiment of the present disclosure, X3 is CR3.
According to an embodiment of the present disclosure, X4 is CR3.
According to one embodiment of the present disclosure, X5 is CR3.
According to an embodiment of the present specification, X2 is C bonded to L1.
According to one embodiment of the present specification, X3 is C bonded to L1.
According to an embodiment of the present specification, X4 is C bonded to L1.
According to an embodiment of the present specification, X5 is C bonded to L1.
According to an embodiment of the present specification, X1 is O, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present specification, X1 is O, any two of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present specification, X1 is O, any three of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present disclosure, X1 is O, and X2 to X5 are N.
According to an embodiment of the present specification, X1 is S, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present disclosure, X1 is S, any two of X2 to X5 are N, and the rest are CR3.
According to an embodiment of the present specification, X1 is S, any three of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present disclosure, X1 is S, and X2 to X5 are N.
According to an embodiment of the present specification, X1 is CR1R2, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present specification, X1 is CR1R2, any two of X2 to X5 are N, and the rest are CR3.
According to an embodiment of the present specification, X1 is CR1R2, any three of X2 to X5 are N, and the rest are CR3.
According to an embodiment of the present disclosure, X1 is CR1 bonded to L1, and X2 to X5 are N.
According to an embodiment of the present specification, X1 is NR, any one of X2 to X5 is N, and the rest is CR3.
According to an embodiment of the present specification, X1 is NR, any two of X2 to X5 are N, and the rest are CR3.
According to an embodiment of the present specification, X1 is NR, any three of X2 to X5 are N, and the rest are CR3.
According to one embodiment of the present specification, X1 is NR, and X2 to X5 are CR3.
According to one embodiment of the present disclosure, X1 is N or CR1 bonded to L1.
According to an embodiment of the present specification, X2 and X3 are CR3, and adjacent R3 are bonded to each other to form an unsubstituted alkyl group or an unsubstituted aryl group substituted or unsubstituted ring.
According to an embodiment of the present specification, X3 and X4 are CR3, and adjacent R3 are bonded to each other to form an unsubstituted alkyl group or an unsubstituted aryl group substituted or unsubstituted ring.
According to an embodiment of the present specification, X4 and X5 are CR3, and adjacent R3 are bonded to each other to form an unsubstituted alkyl group or an unsubstituted aryl group substituted or unsubstituted ring.
According to an embodiment of the present specification, at least one of X2 to X5 is N.
According to one embodiment of the present disclosure, Y1 is O.
According to one embodiment of the present disclosure, Y1 is S.
According to an embodiment of the present disclosure, Y2 is N.
According to one embodiment of the present disclosure, Y2 is CR4.
According to one embodiment of the present disclosure, Y3 is N.
According to one embodiment of the present disclosure, Y3 is CR4.
According to an embodiment of the present disclosure, Y2 and Y3 are N.
According to an embodiment of the present disclosure, Y2 and Y3 are CR4.
According to one embodiment of the present disclosure, Y2 is N, and Y3 is CR4.
According to one embodiment of the present disclosure, Y3 is N, and Y2 is CR4.
According to an embodiment of the present specification, at least one of Y2 to Y7 is N.
According to one embodiment of the present specification, three of Y4 to Y7 are CR5, and the remaining one is C bonded to L1.
According to an embodiment of the present specification, three of Y4 to Y7 are N, and the remaining one is C combined with L1.
According to one embodiment of the present specification, Y4 is C connected to L1.
According to one embodiment of the present specification, Y5 is C connected to L1.
According to one embodiment of the present specification, Y6 is C connected to L1.
According to one embodiment of the present specification, Y7 is C connected to L1.
According to an embodiment of the present specification, ar1 is any one of the following structural formulas, which are substituted or unsubstituted.
According to an embodiment of the present specification, ar1 is any one of the following structural formulas substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, ar1 is any one of the following structural formulas substituted or unsubstituted with methyl, ethyl or aryl.
According to one embodiment of the present specification, ar1 is benzimidazole, substituted or unsubstituted benzoOxazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted benzo +.>Diazole, substituted or unsubstituted ++>Diazole, substituted or unsubstituted thiadiazole, or substituted or unsubstituted naphtho +.>Azole.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and are each independently hydrogen, deuterium, unsubstituted alkyl group, or unsubstituted aryl group, or are combined with each other with adjacent substituents to form an unsubstituted alkyl group or unsubstituted aryl group substituted or unsubstituted ring.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl or anthracenyl, or form a ring substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl or anthracenyl, in combination with each other with the adjacent substituents.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl, or forms an aromatic hydrocarbon ring substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl, or forms a benzene ring substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl.
According to an embodiment of the present specification, the above R and R1 to R3 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl, or forms a naphthalene ring substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl or naphthyl.
According to one embodiment of the present specification, ar1 is benzimidazole substituted or unsubstituted with an alkyl group or an aryl group, imidazole substituted or unsubstituted with an alkyl group or an aryl group, benzo substituted or unsubstituted with an alkyl group or an aryl groupAzole, benzo ++substituted or unsubstituted by alkyl or aryl>Diazole, substituted or unsubstituted by alkyl or aryl ++>Diazole, thiadiazole substituted or unsubstituted by alkyl or aryl, naphtho substituted or unsubstituted by alkyl or aryl->Oxazole, or benzothiazole substituted or unsubstituted with alkyl or aryl.
According to one embodiment of the present specification, ar1 is benzimidazole, imidazole, or benzoAzole,/->Diazole, benzo->Diazole, thiadiazole, naphtho->An azole or a benzothiazole, in combination with a pharmaceutically acceptable salt thereof,
the benzimidazolyl, imidazole and benzoAzole,/->Diazole, benzo->Diazole, thiadiazole, naphtho->The azole or benzothiazole is substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl or terphenyl.
According to an embodiment of the present specification, ar1 is any one of the following structures.
According to an embodiment of the present specification, any one of X6 to X11 is C bonded to L2, at least one of the others is N, and the others are CR6.
According to an embodiment of the present specification, any one of X6 to X11 is C bonded to L2, at least two of the others are N, and the others are CR6.
According to an embodiment of the present specification, any one of X6 to X11 is C bonded to L2, at least three of the others are N, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X6 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X7 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X8 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X9 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X10 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, among the above-mentioned X6 to X11, X11 is N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X6 and X8 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X6 and X7 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, in the above X6 to X11, X6 and X9 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, among X6 to X11, X6, X8, and X10 are N, any one of the others is C bonded to L2, and the others are CR6.
According to an embodiment of the present specification, R6 is deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or may be combined with an adjacent substituent to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.
According to an embodiment of the present specification, R6 is deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms, or may be bonded to each other with an adjacent substituent to form a ring having 6 to 20 carbon atoms.
According to an embodiment of the present specification, ar2 mentioned above is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.
According to an embodiment of the present specification, ar2 is a pyridinyl group substituted or unsubstituted with an aryl group, a pyrimidinyl group substituted or unsubstituted with an aryl group, or a triazinyl group substituted or unsubstituted with an aryl group.
According to an embodiment of the present specification, ar2 is a pyridyl group, a pyrimidinyl group or a triazinyl group, which is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
According to one embodiment of the present specification, ar2 is a pyridyl group, a pyrimidinyl group or a triazinyl group, and the pyridyl group, pyrimidinyl group or triazinyl group is substituted with a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group.
In one embodiment of the present specification, the chemical formula 1 is any one of the following structural formulas.
/>
/>
The substituents of the compound of the above chemical formula 1 may be combined according to a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.
In addition, by introducing various substituents into the core structure of the structure described above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, a substance satisfying the conditions required for each organic layer can be synthesized by introducing substituents mainly used in the hole injection layer substance, the hole transport substance, the light emitting layer substance, and the electron transport layer substance used in manufacturing the organic light emitting device into the above-described core structure.
In addition, the organic light emitting device according to the present invention is characterized by comprising: a first electrode, a second electrode disposed opposite to 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 contains the above-mentioned compound.
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or 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 layer that performs hole injection and hole transport simultaneously, 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 may include a smaller number of organic layers or a greater number of organic layers.
In the organic light emitting device of the present invention, the organic layer may include 1 or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and 1 or more of the layers may include the compound represented by the chemical formula 1.
In another organic light emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by the chemical formula 1.
In the organic light emitting device of the present invention, the electron injection and transport layer includes a compound represented by the above chemical formula 1 and a metal complex.
In the organic light emitting device of the present invention, the electron injection and transport layer includes the compound represented by the above chemical formula 1 and lithium quinolinate.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:5 to 5:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of formula 1 and lithium quinolinate at a weight ratio of 1:10 to 10:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of formula 1 and lithium quinolinate in a weight ratio of 1:5 to 5:1.
In the organic light emitting device of the present invention, the above electron injection and transport layer may include the compound of formula 1 and lithium quinolinate in a weight ratio of 1:3 to 3:1.
In the organic light emitting device of the present invention, the organic layer includes a hole blocking layer including the compound of formula 1.
In the organic light emitting device of the present invention, the organic layer may include 1 or more layers of a hole injection layer, a hole transport layer, and a layer in which hole injection and hole transport are simultaneously performed, and 1 or more layers of the layers may include the compound represented by the chemical formula 1.
In another organic light emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by chemical formula 1.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode
The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, an organic layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above organic layer 3.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above electron injection and transport layer 8.
For example, the organic light emitting device according to the present invention may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, and then an organic layer including 1 or more layers selected from a hole injection layer, a hole transport layer, a layer in which hole transport and hole injection are performed simultaneously, a light emitting layer, an electron transport layer, an electron injection layer, and a layer in which electron transport and electron injection are performed simultaneously is formed on the anode, and then a substance usable as a cathode is deposited on the organic layer to manufacture the anode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, but is not limited thereto, and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected 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, and alloys thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of 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/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the migration of holes can be prevented.
According to an embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.
[ chemical formula HI-1]
In the above-mentioned chemical formula HI-1,
l301 to L303 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r301 to R303 are the same as or different from each other, each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and any one selected from combinations thereof, or are combined with each other with an adjacent group to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, the above R301 to R303 are the same as or different from each other, each independently is any one selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.
According to an embodiment of the present specification, the above-mentioned R301 to R303 are the same as or different from each other, each independently is any one selected from the group consisting of a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a biphenyl group, and a combination thereof.
According to an embodiment of the present specification, the above-mentioned L301 to L303 are the same as or different from each other, and each is independently a direct bond, arylene or heteroarylene.
According to one embodiment of the present specification, the above formula HI-1 is represented by the following compound.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
According to an embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.
[ chemical formula HT-2]
In the above-mentioned chemical formula HT-2,
r315 to R317 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or any one selected from combinations thereof, or are combined with each other with an adjacent group to form a substituted or unsubstituted ring,
r315 is an integer of 1 to 5, and when R315 is 2 or more, 2 or more of R315 are the same or different from each other,
r316 is an integer of 1 to 5, and when R316 is 2 or more, 2 or more R316 are the same or different from each other.
According to an embodiment of the present disclosure, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and combinations thereof.
According to an embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a biphenyl group, and a combination thereof.
According to one embodiment of the present specification, the above formula HT-2 is represented by the following compounds.
A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron-inhibiting layer may be provided between the hole-transporting layer and the light-emitting layer. The electron-inhibiting layer may be formed using the spiro compound described above or a material known in the art.
The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxy-quinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene ethylene)Alkenyl) (PPV) polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
According to an embodiment of the present specification, the body includes a compound represented by the following chemical formula H-1, but is not limited thereto.
[ chemical formula H-1]
In the above-mentioned chemical formula H-1,
l20 and L21 are the same or different from each other and each independently is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group of 2 valency,
ar20 and Ar21 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R201 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
r201 is an integer of 1 to 8, and when R201 is 2 or more, 2 or more R201 are the same or different from each other.
In one embodiment of the present specification, L20 and L21 are the same or different from each other, and each is independently a direct bond, a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
In an embodiment of the present specification, the above L20 and L21 are the same or different from each other, and each is independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothienyl group.
In one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; thienyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; dibenzofuranyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothienyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
In an embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a terphenyl group, a naphthyl group substituted or unsubstituted with deuterium, a thienyl group substituted or unsubstituted with phenyl group, a phenanthryl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothienyl group, or a naphthobenzothienyl group.
In one embodiment of the present specification, ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.
According to an embodiment of the present disclosure, R201 is hydrogen.
According to an embodiment of the present specification, the above formula H-1 is represented by the following compound.
When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent substances such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium), tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin) and the like can be used; or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), but are not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Irpic and other phosphorescent substances; or a fluorescent substance such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO polymer or PPV polymer, but is not limited thereto.
According to an embodiment of the present specification, the dopant includes a compound represented by the following chemical formula D-1, but is not limited thereto.
[ chemical formula D-1]
In the above-mentioned chemical formula D-1,
t1 to T6 are identical to or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl,
t5 and t6 are each an integer of 1 to 4,
when T5 is 2 or more, T5 of 2 or more are the same or different from each other,
When T6 is 2 or more, T6 s of 2 or more are the same or different from each other.
According to an embodiment of the present specification, T1 to T6 are the same or different from each other, and each is independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, the above-mentioned T1 to T6 are the same or different from each other, each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a nitrile group or a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
According to an embodiment of the present specification, the above-mentioned T1 to T6 are the same or different from each other, and are each independently hydrogen, phenyl substituted with a halogen group, or phenyl substituted with deuterium.
According to an embodiment of the present specification, the above chemical formula D-1 is represented by the following compound.
/>
A hole-suppressing layer may be provided between the electron-transporting layer and the light-emitting layer, and materials known in the art may be used.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for the purpose of improving the electron transfer can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like, Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the electron injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The method of manufacturing the compound of chemical formula 1 above and the manufacture of an organic light emitting device using the same are specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
In the following reaction formulae, the kinds and numbers of substituents can be appropriately selected according to the known starting materials by those skilled in the art to synthesize various types of intermediates. The type of reaction and the reaction conditions may utilize techniques known in the art.
[ reaction type 1]
In the above reaction formula 1, the definitions other than Y are the same as those described above, and Y is a halogen group, preferably a bromo group or a chloro group.
The above reaction is a carbon substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactive groups used for the carbon substitution reaction may be modified according to techniques known in the art. The above-described production method can be more specifically described in the production example described later.
The compound of formula 1 described in the present specification can be produced by appropriately combining the production formula described in the examples of the present specification and the intermediate based on general technical knowledge.
Synthesis example
Synthesis example 1: production of Compound E1
E1-A (20 g,57.7 mmol) and E1-B (25.1 g,57.7 mmol) were added to 400ml of two under nitrogenIn an alkane (Diox), stirring and refluxing. Then, potassium phosphate (36.7 g,173 mmol) was dissolved in 37ml of water and added thereto, and after stirring well, dibenzylideneacetone palladium (1 g,1.7 mmol) and tricyclohexylphosphine (1 g,3.5 mmol) were added thereto. After the reaction for 6 hours, the resultant solid was filtered after cooling to room temperature. The solid was poured into 1072mL of chloroform and dissolved, 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 yield yellow solid compound E1 (5.4 g, 15%).
MS:[M+H] + ＝620
Synthesis example 2: production of Compound E2
The compound E2 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝646
Synthesis example 3: production of Compound E3
The compound E3 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝631
Synthesis example 4: production of Compound E4
The compound E4 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝604
Synthesis example 5: production of Compound E5
The compound E5 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝654
Synthesis example 6: production of Compound E6
The compound E6 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝706
Synthesis example 7: production of Compound E7
The compound E7 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝604
Synthesis example 8: production of Compound E8
The compound E8 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝707
Synthesis example 9: production of Compound E9
The compound E9 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝679
Synthesis example 10: production of Compound E10
The compound E10 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝654
Synthesis example 11: production of Compound E11
The compound E11 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝680
Synthesis example 12: production of Compound E12
The compound E12 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝705
Experimental example
Experimental example 1
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following compound HI-A was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT,)>) And the following compound HT-A->Vacuum evaporation is performed to form a hole transport layer.
Then, on the hole transport layer, the film thickness is set to beThe following compounds BH and BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, the compound E1 produced in Synthesis example 1 and the following compound [ LiQ ]]Vacuum evaporation was performed at a weight ratio of 1:1 to obtain a solution of lithium quinolineForm electron transport and injection layers. On the electron transport and injection layer, lithium fluoride (LiF) is added in sequence +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 ～5×10 -8 The support is thus fabricated into an organic light emitting device.
Experimental examples 2 to 12
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of table 1 below was used instead of the compound E1 of experimental example 1.
Comparative examples 1 to 16
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of table 1 below was used instead of the compound E1 of experimental example 1. The compounds of ET-1 to ET-16 used in table 1 below are shown below.
The organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples were subjected to a temperature of 10mA/cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20mA/cm 2 The time (T) at which the initial luminance was 90% was measured at the current density of (2) 90 ). The results are shown in table 1 below.
TABLE 1
/>
As described in Table 1 above, it was confirmed that in the case of using the organic light-emitting device of the compound represented by chemical formula 1 of the present inventionVoltage, efficiency and/or lifetime (T 90 ) Exhibits excellent characteristics.
Specifically, the compound represented by chemical formula 1 of the present invention is characterized in that an N-containing ring group represented by chemical formula 2 is linked to a benzene ring containing a cyano group through a linking group, electron mobility is increased due to 2N-containing ring groups in a molecule, thereby increasing efficiency of an organic light emitting device, and electron injection characteristics are adjusted by containing 1 cyano group in a molecule, thereby exhibiting a result of increasing the life span of the organic light emitting device.
Comparing experimental examples 1 to 12 of table 1 with comparative experimental examples 1 to 13, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention has a structure including a benzene ring substituted with a cyano group, and thus, it is possible to demonstrate significantly excellent characteristics in efficiency and lifetime compared to the organic light emitting device using the compound not including a cyano group.
Comparing experimental examples 1 to 12 of table 1 above with comparative experimental examples 14 to 16, it can be confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention shows significantly superior characteristics in terms of efficiency compared to the organic light emitting device using the compound substituted with the carbazole and the benzonaphthofuran compound.
Claims (12)
1. A compound of the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
l1 and L2 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
ar1 is represented by the following chemical formula 2 or 3,
[ chemical formula 2]
[ chemical formula 3]
In the chemical formula 2 described above, the chemical formula,
x1 is NR, O, S, CR R2, N linked to L1, or CR1 linked to L1,
x2 to X5 are identical to or different from each other and are each independently N, CR3 or C linked to L1,
R and R1 to R3 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are capable of forming a substituted or unsubstituted ring in combination with each other with the adjacent substituents,
however, X1 is NR, or at least one of X2 to X5 is N,
x1 is N connected with L1, CR1 connected with L1, or any one of X2 to X5 is C connected with L1,
in the chemical formula 3 described above, the chemical formula,
y1 is O or S, and the total number of the components is equal to or less than zero,
y2 and Y3 are identical to or different from each other and are each independently N or CR4,
y4 to Y7 are identical to or different from each other and are each independently N, CR5 or C linked to L1,
any one of Y4 to Y7 is C connected to L1,
r4 and R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are capable of forming a substituted or unsubstituted ring in combination with each other with the adjacent substituents,
ar2 is represented by the following chemical formula 4,
[ chemical formula 4]
In the chemical formula 4 described above, the chemical formula,
x6 to X11 are identical to or different from each other and are each, independently of one another, N, CR6 or C combined with L2,
any one of X6 to X11 is C bonded to L2, at least one of the others is N,
r6 is deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or can combine with adjacent substituents to each other to form a substituted or unsubstituted ring.
2. The compound of claim 1, wherein L1 and L2 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
3. The compound of claim 1, wherein at least one of X6 to X11 is N, the remainder are CR6.
4. The compound of claim 1, wherein at least one of X2 to X5 is N.
5. The compound of claim 1, wherein at least one of Y2 to Y7 is N.
6. The compound of claim 1, wherein R and R1 to R3 are the same or different from each other, each independently hydrogen, deuterium, unsubstituted alkyl, or unsubstituted aryl, or combine with adjacent substituents with each other to form a ring substituted or unsubstituted with unsubstituted alkyl or unsubstituted aryl.
7. The compound of claim 1, wherein Ar1 is benzimidazole substituted or unsubstituted with alkyl or aryl, imidazole substituted or unsubstituted with alkyl or aryl, benzo substituted or unsubstituted with alkyl or aryl Azole, benzo ++substituted or unsubstituted by alkyl or aryl>Diazole, substituted or unsubstituted by alkyl or aryl ++>Diazole, thiadiazole substituted or unsubstituted by alkyl or aryl, naphtho substituted or unsubstituted by alkyl or aryl->Oxazole, or benzothiazole substituted or unsubstituted with alkyl or aryl.
8. The compound of claim 1, wherein Ar2 is substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted triazinyl.
9. The compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
In the chemical formulas 1-1 to 1-6, the L1, L2, ar1 and Ar2 are as defined in chemical formula 1.
10. The compound of claim 1, wherein the chemical formula 1 is any one of the following compounds:
11. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to 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 contains the compound according to any one of claims 1 to 10.
12. The organic light-emitting device according to claim 11, wherein the organic layer includes 1 or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and 1 or more of the layers contains the compound represented by the chemical formula 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020220003739A KR20230108395A (en) | 2022-01-11 | 2022-01-11 | Compound and organic light emitting device comprising same |
| KR10-2022-0003739 | 2022-01-11 | ||
| PCT/KR2023/000453 WO2023136586A1 (en) | 2022-01-11 | 2023-01-10 | Compound and organic light-emitting device comprising same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117580832A true CN117580832A (en) | 2024-02-20 |
Family
ID=87279311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202380012553.6A Pending CN117580832A (en) | 2022-01-11 | 2023-01-10 | Compound and organic light emitting device comprising the same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20230108395A (en) |
| CN (1) | CN117580832A (en) |
| WO (1) | WO2023136586A1 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100696461B1 (en) * | 2003-08-07 | 2007-03-19 | 삼성에스디아이 주식회사 | Iridium compound and organic electroluminescence device employing the same |
| US8273467B2 (en) * | 2006-02-28 | 2012-09-25 | Fujifilm Corporation | Organic electroluminescent device |
| JP2012018958A (en) * | 2010-07-06 | 2012-01-26 | Konica Minolta Holdings Inc | Organic photoelectric conversion element and solar cell using the same |
| ES2887148T3 (en) | 2015-03-25 | 2021-12-21 | Nat Cancer Ct | Therapeutic agent against bile duct cancer |
| KR102382164B1 (en) * | 2019-07-05 | 2022-04-04 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| CN113812015A (en) * | 2019-11-29 | 2021-12-17 | 株式会社Lg化学 | Organic light emitting device |
-
2022
- 2022-01-11 KR KR1020220003739A patent/KR20230108395A/en active Search and Examination
-
2023
- 2023-01-10 WO PCT/KR2023/000453 patent/WO2023136586A1/en active Application Filing
- 2023-01-10 CN CN202380012553.6A patent/CN117580832A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2023136586A1 (en) | 2023-07-20 |
| KR20230108395A (en) | 2023-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111372938B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN112204026B (en) | Polycyclic compound and organic light emitting diode including the same | |
| CN112585145B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN112912370B (en) | Polycyclic compound and organic light-emitting element including the same | |
| CN111936479B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN113056471B (en) | Compound and organic light-emitting diode comprising same | |
| CN111032645B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN112154548A (en) | Organic light emitting device | |
| CN113056468B (en) | Compound and organic light emitting device comprising the same | |
| KR102181840B1 (en) | Multicyclic compound and organic light emitting device comprising the same | |
| CN116057039B (en) | Compound and organic light emitting device comprising the same | |
| CN112912365B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN113056463B (en) | Compound and organic light emitting device comprising the same | |
| CN112204030B (en) | Compound and organic light emitting device comprising the same | |
| CN113924666A (en) | Organic light emitting device | |
| CN117580832A (en) | Compound and organic light emitting device comprising the same | |
| CN112088161B (en) | Polycyclic compound and organic light emitting diode including the same | |
| CN117794916A (en) | Compound and organic light emitting device comprising the same | |
| CN112771030B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN113994497B (en) | Organic light emitting device | |
| CN116583519A (en) | Compound and organic light emitting device comprising the same | |
| CN116685587A (en) | Compound and organic light emitting device comprising the same | |
| CN117377670A (en) | Compound and organic light emitting device comprising the same | |
| CN117940423A (en) | Compound and organic light emitting device comprising the same | |
| CN117177978A (en) | Compound and organic light emitting device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |