CN112010840A - 有机电致发光化合物和包含其的有机电致发光装置 - Google Patents
有机电致发光化合物和包含其的有机电致发光装置 Download PDFInfo
- Publication number
- CN112010840A CN112010840A CN201910807504.7A CN201910807504A CN112010840A CN 112010840 A CN112010840 A CN 112010840A CN 201910807504 A CN201910807504 A CN 201910807504A CN 112010840 A CN112010840 A CN 112010840A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- organic electroluminescent
- layer
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 86
- 239000010410 layer Substances 0.000 claims abstract description 95
- 239000012044 organic layer Substances 0.000 claims abstract description 35
- 230000005525 hole transport Effects 0.000 claims abstract description 18
- 230000000903 blocking effect Effects 0.000 claims abstract description 9
- -1 nitro, hydroxyl Chemical group 0.000 claims description 43
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 42
- 230000015572 biosynthetic process Effects 0.000 description 58
- 238000003786 synthesis reaction Methods 0.000 description 58
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000004440 column chromatography Methods 0.000 description 28
- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 15
- 239000010949 copper Substances 0.000 description 14
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- 125000005605 benzo group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- WADSQZHEAXPENM-UHFFFAOYSA-N 1h-pyrrol-2-ylboronic acid Chemical compound OB(O)C1=CC=CN1 WADSQZHEAXPENM-UHFFFAOYSA-N 0.000 description 6
- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- KQPADKUSNKOJID-UHFFFAOYSA-N 1,3-benzothiazol-2-ylboronic acid Chemical compound C1=CC=C2SC(B(O)O)=NC2=C1 KQPADKUSNKOJID-UHFFFAOYSA-N 0.000 description 3
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 3
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126545 compound 53 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- JWUGKJKBCKJFOU-UHFFFAOYSA-N 1,3-thiazol-2-ylboronic acid Chemical compound OB(O)C1=NC=CS1 JWUGKJKBCKJFOU-UHFFFAOYSA-N 0.000 description 2
- YKFRPCRADQOKOA-UHFFFAOYSA-N 10-(4-bromophenyl)-9,9-dimethylacridine Chemical compound C12=CC=CC=C2C(C)(C)C2=CC=CC=C2N1C1=CC=C(Br)C=C1 YKFRPCRADQOKOA-UHFFFAOYSA-N 0.000 description 2
- WKVREFXPVUWUGC-UHFFFAOYSA-N 2,7-dibromo-9,10-dihydroacridine Chemical compound BrC1=CC=2CC3=CC(=CC=C3NC2C=C1)Br WKVREFXPVUWUGC-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JBWRZTKHMKVFMQ-UHFFFAOYSA-N 3,6-dibromo-9-phenylcarbazole Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 JBWRZTKHMKVFMQ-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 125000003943 azolyl group Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- JTRWBBPLLGECJS-UHFFFAOYSA-N (9,9-dimethylfluoren-3-yl)boronic acid Chemical compound OB(O)C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 JTRWBBPLLGECJS-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical group C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- DGMMVPUHMXJKGE-UHFFFAOYSA-N 2,5-dibromo-4-phenylpyridine Chemical compound BrC1=NC=C(C(=C1)C1=CC=CC=C1)Br DGMMVPUHMXJKGE-UHFFFAOYSA-N 0.000 description 1
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 1
- FBQFCXDBCPREBP-UHFFFAOYSA-N 2-(4-bromophenyl)pyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=CC=N1 FBQFCXDBCPREBP-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- NVORBAXCWWFMSA-UHFFFAOYSA-N 3,7-dibromo-10h-phenothiazine Chemical compound C1=C(Br)C=C2SC3=CC(Br)=CC=C3NC2=C1 NVORBAXCWWFMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- HSNBRDZXJMPDGH-UHFFFAOYSA-N 5-bromo-2-iodopyridine Chemical compound BrC1=CC=C(I)N=C1 HSNBRDZXJMPDGH-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-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
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 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
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 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
- 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
- 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
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 230000003287 optical effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D403/14—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 three or more hetero 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- 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
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
公开了由式I表示的新有机电致发光化合物。采用所述有机电致发光化合物作为用于有机电致发光装置的至少一个有机层例如发光层、空穴传输层、电子传输层、电子阻挡层和/或覆盖层的材料,实现了装置的优异发光特性(包括高的发光效率和量子效率)。还公开了包含所述有机电致发光化合物的有机电致发光装置。
Description
技术领域
本发明涉及有机电致发光化合物,并且更具体地涉及用作用于有机电致发光装置的至少一个有机层例如发光层、空穴传输层、电子传输层、电子阻挡层和/或覆盖层的材料的有机电致发光化合物。本发明还涉及采用所述有机电致发光化合物的有机电致发光装置,实现了大大改善的发光特性例如高的发光效率和量子效率。
背景技术
即使在透明基底上也可以制造有机电致发光装置。此外,与等离子体显示面板和无机电致发光(EL)显示器相比,有机电致发光装置可以在10V或更低的低电压下以相对低的功耗驱动并且具有良好的颜色表现。有机电致发光装置可以显示三种颜色:绿色、蓝色和红色。由于这些优点,有机电致发光装置作为下一代显示装置已成为备受关注的主题。
用于有机层的材料的稳定性和效率是制造具有上述优异特性的有机电致发光装置的先决条件。即,为了有机电致发光装置的上述优异特性,有机电致发光装置应由稳定且有效的有机层材料(例如,空穴注入材料、空穴传输材料、发光材料、电子传输材料、和电子注入材料)支撑。然而,用于有机电致发光装置的稳定且有效的有机层材料仍处于开发的早期阶段。
因此,为了良好的稳定性、高效率、长寿命和大尺寸的有机电致发光装置,需要在效率和寿命特性方面进一步改善。特别地,强烈需要开发用于有机电致发光装置的有机层的新材料。
在这一方面,最近已经进行了相当大的研究努力以改善用于有机电致发光装置的构成层(特别地,空穴传输层)的有机材料的迁移率。
已经有许多研究旨在通过改变有机层材料的性能来改善有机电致发光装置的特性。此外,用于通过优化阳极与阴极之间的层的光学厚度来改善色纯度和增强装置的发光效率的技术被认为是用于改善装置性能的关键因素。例如,在电极上形成覆盖层实现了增加的发光效率和高的色纯度。
发明内容
本发明旨在提供用作用于有机电致发光装置的至少一个有机层的材料的新有机电致发光化合物以及包含所述有机电致发光化合物的有机电致发光装置,实现了装置的优异发光特性(包括高的发光效率和量子效率)。
本发明的一个方面提供了由式I表示的有机电致发光化合物:
下面描述式I的结构特征,并且式I中的X1、X2、Y、R1至R8、L和Ar如以下所限定。
使用根据本发明的有机电致发光化合物作为用于有机电致发光装置的至少一个有机层(例如发光层、空穴传输层、电子传输层、电子阻挡层和/或覆盖层)的材料确保了装置的优异发光特性(例如高的发光效率和量子效率)。因此,本发明的有机电致发光化合物适合用于各种显示装置。
附图说明
结合附图,本发明的这些和/或其他方面和优点将从实施方案的以下描述中变得明显并且更容易理解,在附图中:
图1示出了根据本发明的有机电致发光化合物的结构式。
具体实施方式
现在将更详细地描述本发明。
本发明涉及由式I表示的具有优异的发光特性(例如高的发光效率和量子效率)的有机电致发光化合物:
其中X1和X2各自独立地为O、S或NR9,Y为单键、O、S、CR10R11或NR12,R9至R12各自独立地选自氢、氘、经取代或未经取代的C1至C10烷基、经取代或未经取代的C6至C30芳基、经取代或未经取代的C3至C30杂芳基、与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C6至C30芳基、和与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C3至C30杂芳基,R1至R8各自独立地选自氢、氘、卤素基团、氰基、经取代或未经取代的C1至C10烷基、经取代或未经取代的C6至C30芳基、经取代或未经取代的C3至C30杂芳基、与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C6至C30芳基、和与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C3至C30杂芳基,条件是R1至R8任选地彼此键合或者与一个或更多个相邻取代基连接而形成碳原子任选地经选自氮(N)原子、硫(S)原子和氧(O)原子的一个或更多个杂原子取代的至少一个脂环族或芳族的单环或多环,L为单键或者选自经取代或未经取代的C6至C30亚芳基和经取代或未经取代的C3至C30亚杂芳基,n为0至3的整数,Ar选自经取代或未经取代的C6至C30芳基、经取代或未经取代的C3至C30杂芳基、经取代或未经取代的芴基、与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C6至C30芳基、和与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C3至C30杂芳基,以及m为1至3的整数。
R1至R12、L和Ar的定义中的术语“经取代”表示经选自氢、氘、卤素基团、氰基、硝基、羟基、甲硅烷基、烷基、环烷基、烷氧基、烯基、芳基、杂环基及其组合的一个或更多个取代基取代。相同定义中的术语“未经取代的”表示不具有取代基。
具体地,经取代的亚芳基可以为例如经一个或更多个其他取代基取代的苯基、联苯基、萘基、芴基、芘基、菲基、苝基、并四苯基和蒽基。
经取代的亚杂芳基为经一个或更多个其他取代基取代的吡啶基、噻吩基、三嗪基、喹啉基、菲咯啉基、咪唑基、噻唑基、唑基、咔唑基、和它们的稠合杂环基(例如,苯并喹啉基、苯并咪唑基、苯并唑基、苯并噻唑基、苯并咔唑基、二苯并噻吩基和二苯并呋喃基)。
下面具体例举以上取代基而没有限制。
烷基可以为直链的或支化的。烷基中的碳原子数没有特别限制,但优选为1至20。烷基的具体实例包括但不限于甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基丁基、1-乙基丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基丙基、1,1-二甲基丙基、异己基、2-甲基戊基、4-甲基己基、和5-甲基己基。
烷氧基可以为直链的或支化的。烷氧基中的碳原子数没有特别限制,但优选为1至20,只要避免空间位阻即可。烷氧基的具体实例包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基(isopropoxy)、异丙基氧基(i-propyloxy)、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基和对甲基苄氧基。
芳基可以为单环的或多环的。芳基中的碳原子数没有特别限制,但优选为6至30。单环芳基的实例包括苯基、联苯基、三联苯基和茋基,但本发明的范围不限于此。多环芳基的实例包括萘基、蒽基、菲基、芘基、苝基、并四苯基、基、芴基、苊基(acenaphathcenyl)、三亚苯基和荧蒽基,但本发明的范围不限于此。
杂芳基是指包含选自O、N和S中的一个或更多个杂原子的杂环基。杂芳基中的碳原子数优选为2至30。杂芳基的具体实例包括但不限于噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪、三唑基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、二苯并呋喃基、菲咯啉基、噻唑基、异唑基、二唑基、噻二唑基、苯并噻唑基、吩噻嗪基(phenothiazinyl)、吩嗪基和吩噻嗪基(phenothiazine group)。
甲硅烷基的具体实例包括但不限于三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、和苯基甲硅烷基。
卤素基团的具体实例包括氟(F)、氯(Cl)和溴(Br)。
根据本发明的式I的有机电致发光化合物由于其结构特征而可以用于形成有机电致发光装置的各种不同有机层。更具体地,式I的有机电致发光化合物可以用作用于有机电致发光装置的发光层或覆盖层的材料。
具体地,根据本发明的式I的有机电致发光化合物选自但不限于:
本发明的有机电致发光化合物由于其特征骨架而表现出固有特性,并且由于引入到骨架中的部分的固有特性而具有各种各样的特性。因此,本发明的有机电致发光化合物可以用作用于有机电致发光装置的各种各样的有机层例如发光层、覆盖层、空穴传输层、电子传输层和/或电子阻挡层的材料,实现装置的进一步改善的发光特性(包括高的发光效率)。
本发明的化合物可以通过本领域已知的合适方法应用于有机电致发光装置。
根据本发明的一个实施方案的有机电致发光装置可以包括第一电极、第二电极和布置在其间的至少一个有机层。所述有机电致发光装置可以使用本领域已知的合适材料通过一般方法制造,不同之处在于使用本发明的有机电致发光化合物形成有机层。
有机电致发光装置的有机层可以具有单层结构。或者,可以设置复数个有机层。在这种情况下,有机层具有多层层合体结构。例如,有机层的结构可以包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、电子阻挡层、空穴阻挡层和覆盖层,但不限于此。有机层的数目没有限制,并且可以增加或减少。
根据一个实施方案,有机电致发光装置可以包括基底、第一电极(阳极)、一个或更多个有机层、第二电极(阴极)和形成在第一电极下方(底部发射型)或第二电极上(顶部发射型)的覆盖层。
当有机电致发光装置为顶部发射型时,来自发光层的光被发射至阴极并且穿过具有相对高的折射率的使用本发明的化合物形成的覆盖层(CPL)。光的波长在覆盖层中被放大,导致发光效率增加。此外,当有机电致发光装置为底部发射型时,可以将本发明的化合物用于覆盖层中以基于相同的原理提高有机电致发光装置的发光效率。
根据本发明的有机电致发光装置的有机层的优选结构将在下面的实施例部分中更详细地说明。
本发明的有机电致发光装置可以通过以下制造:通过物理气相沉积(PVD)法(例如溅射或电子束蒸镀)在基底上沉积金属、导电金属氧化物或其合金以形成阳极,形成包括空穴注入层、空穴传输层、发光层、和电子传输层的有机层,以及在有机层上沉积阴极材料。
或者,有机电致发光装置可以通过在基底上按以下顺序沉积阴极材料、有机层材料和阳极材料来制造。有机层可以具有包括空穴注入层、空穴传输层、发光层和电子传输层的多层结构,但不限于该结构。或者,有机电致发光装置可以仅包括一个有机层。有机层可以通过使用各种各样的聚合物材料的溶剂法而不是通过沉积法来形成。溶剂法可以为例如旋涂、浸涂、刮刀涂覆、丝网印刷、喷墨印刷或热转印。在这种情况下,可以减少有机层的数目。
优选地,阳极材料具有高功函数以使空穴容易地注入有机层中。适用于本发明的阳极材料的具体实例包括但不限于:金属,例如钒、铬、铜、锌和金,及其合金;金属氧化物,例如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);金属和氧化物的组合,例如ZnO:Al和SnO2:Sb;和导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDT)、聚吡咯和聚苯胺。
优选地,阴极材料具有低功函数以使电子容易地注入有机层。合适的阴极材料的具体实例包括但不限于:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,及其合金;和多层结构材料,例如LiF/Al和LiO2/Al。
空穴注入材料优选为在低电压下可以接收从阳极注入的空穴的材料。空穴注入材料的最高占据分子轨道(HOMO)优选在阳极材料的功函数与相邻有机层材料的HOMO之间。合适的空穴注入材料的具体实例包括但不限于金属卟啉、低聚噻吩、基于芳基胺的有机材料、六腈六氮杂苯并菲、基于喹吖啶酮的有机材料、基于苝的有机材料、基于蒽醌、基于聚苯胺和基于聚噻吩的导电聚合物。
空穴传输材料为可以接收从阳极或空穴注入层传输的空穴并且可以将空穴转移至发光层的材料。具有高空穴迁移率的材料适合作为空穴传输材料。合适的空穴传输材料的具体实例包括基于芳基胺的有机材料、导电聚合物和由共轭链段和非共轭链段组成的嵌段共聚物。根据本发明的有机电致发光化合物的使用确保了装置的进一步改善的低的电压驱动特性、高的发光效率和优异的寿命特性。
发光材料为可以接收来自空穴传输层的空穴和来自电子传输层的电子并且使其重组以发射在可见光范围内的光的材料。优选对荧光和磷光具有高量子效率的材料作为发光材料。合适的发光材料的具体实例包括但不限于8-羟基喹啉铝配合物(Alq3)、基于咔唑的化合物、二聚苯乙烯基化合物、BAlq、10-羟基苯并喹啉-金属化合物、基于苯并唑的化合物、基于苯并噻唑的化合物和基于苯并咪唑的化合物、基于聚(对亚苯基亚乙烯基)(PPV)的聚合物、螺环化合物、聚芴和红荧烯。
电子传输材料为可以接收从阴极注入的电子并且可以将电子转移至发光层的材料。具有高电子迁移率的材料适合作为电子传输材料。合适的电子传输材料的具体实例包括但不限于8-羟基喹啉Al配合物(Alq3)、Alq3配合物、有机自由基化合物、羟基黄酮-金属配合物。
根据所使用的材料,本发明的有机电致发光装置可以为顶部发射型、底部发射型或双发射型。
即使在有机电子装置(包括有机太阳能电池、有机光电导体和有机晶体管)中,本发明的有机电致发光化合物也可以基于与应用于有机电致发光装置的原理类似的原理发挥其功能。
将参照以下实施例更详细地说明本发明。然而,提供这些实施例是为了举例说明性目的,而不是用于限制本发明的范围。对于本领域技术人员明显的是,在不脱离本发明的范围和精神的情况下可以进行各种修改和改变。
合成例1:化合物1的合成
(1)制备例1:化合物1的合成
将甲苯(100mL)、H2O(30mL)和乙醇(30mL)添加至3,6-二溴-9-苯基-9H-咔唑(10g,0.025mol,Sigma-Aldrich)、苯并[d]唑-2-基硼酸(8.97g,0.055mol,mascot)、碳酸钾(13.78g,0.100mol,Sigma-Aldrich)和Pd(PPh3)4(1.73g,0.001mol,Sigma-Aldrich)。在95℃下将混合物在搅拌下回流6小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供11.0g(产率92.3%)化合物1。
H-NMR(200MHz,CDCl3):δppm,1H(8.18/d,8.00/d,7.87/d,7.69/d,7.45/m),2H(7.77/s,7.58/m,7.50/d),4H(7.74/m 7.39/d)
LC/MS:m/z=477[(M+1)+]
合成例2:化合物53的合成
(1)制备例1:中间体53-1的合成
将THF(100mL)、H2O(30mL)和乙醇(30mL)添加至3,6-二溴-9H-咔唑(10g,0.035mol,TCI)、苯并[d]唑-2-基硼酸(30.43g,0.077mol,mascot)、碳酸钾(17.01g,0.123mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(2.13g,0.002mol,Sigma-Aldrich)。在80℃下将混合物在搅拌下回流6小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.1g(产率57.5%)中间体53-1。
(2)制备例2:中间体53-2的合成
将甲苯(100mL)、H2O(30mL)和乙醇(30mL)添加至1-溴-4-碘苯(10g,0.035mol,Sigma-Aldrich)、(9,9-二甲基-9H-芴-3-基)硼酸(8.42g,0.035mol,mascot)、碳酸钾(9.77g,0.071mol,Sigma-Aldrich)和Pd(PPh3)4(1.23g,0.001mol,Sigma-Aldrich)。在95℃下将混合物在搅拌下回流6小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供8.5g(产率68.9%)中间体53-2。
(3)制备例3:化合物53的合成
将DMF(100mL)添加至中间体53-1(10g,0.025mol)、中间体53-2(10.4g,0.030mol)、碳酸钾(6.89g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.9g,0.003mol,Sigma-Aldrich)和Cu(3.17g,0.050mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流6小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供14.3g(产率85.7%)化合物53。
H-NMR(200MHz,CDCl3):δppm,1H(8.18/d,8.06/s,8.00/d,7.69/d,7.61/d,7.55/d,7.53/d,7.38/m,7.28/m,1.72/m),2H(7.87/d,7.79/d,7.77/s,7.68/d),4H(7.74/m,7.39/d)
LC/MS:m/z=669[(M+1)+]
合成例3:化合物64的合成
(1)制备例1:化合物64的合成
将DMF(100mL)添加至中间体53-1(10g,0.025mol)、9-(4-溴苯基)-9H-咔唑(9.6g,0.030mol,TCI)、碳酸钾(6.89g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.9g,0.003mol,Sigma-Aldrich)和Cu(3.170g,0.050mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供11.3g(产率70.6%)化合物64。
H-NMR(200MHz,CDCl3):δppm,1H(8.55/d,8.18/d,8.12/d,8.00/d,7.94/d,7.87/d,7.69/d,7.63,d,7.50/m,7.33/m,7.29/m,7.25/m),2H(7.77/s),4H(7.74/m,7.62/d,7.39/d)
LC/MS:m/z=642[(M+1)+]
合成例4:化合物75的合成
(1)制备例1:中间体75-1的合成
将甲苯(100mL)、乙醇(30mL)和H2O(30mL)添加至1-溴-4-碘苯(10g,0.035mol)、二苯并[b,d]噻吩-2-基硼酸(8.06g,0.035mol,mascot)、碳酸钾(9.77g,0.071mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.23g,0.001mol,Sigma-Aldrich)。在90℃下将混合物在搅拌下回流6小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.6g(产率63.4%)中间体75-1。
(2)制备例2:化合物75的合成
将DMF(100mL)添加至中间体53-1(10g,0.030mol)、中间体75-1(14.2g,0.035mol)、碳酸钾(8.15g,0.060mol,Sigma-Aldrich)、二苯并-18-冠-6(1.06g,0.003mol,Sigma-Aldrich)和Cu(3.75g,0.060mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供11.9g(产率72.4%)化合物75。
H-NMR(200MHz,CDCl3):δppm,1H(8.45/d,8.18/d,7.98/d,7.87/d,7.86/d,7.69/d,7.52/m,7.50/m),2H(7.79/d,7.77/s,7.68/d),3H(8.00/d),4H(7.74/m,7.39/d)
LC/MS:m/z=659[(M+1)+]
合成例5:化合物97的合成
(1)制备例1:化合物97的合成
将DMF(100mL)添加至中间体53-1(10g,0.025mol)、10-(4-溴苯基)-9,9-二甲基-9,10-二氢吖啶(10.9g,0.030mol,mascot)、碳酸钾(6.89g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.90g,0.003mol,Sigma-Aldrich)和Cu(3.17g,0.050mol,Sigma-Aldrich)。在160℃下将混合物在搅拌下回流9小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供12.1g(产率70.9%)化合物97。
H-NMR(200MHz,CDCl3):δppm,1H(8.18/d,8.00/d,7.87/d,7.69/d),2H(7.77/s,7.37/d,7.05/d,7.02/m,6.73/m,6.63/d,6.55/d,1.72/m)4H(7.74/m,7.39/d)
LC/MS:m/z=684[(M+1)+]
合成例6:化合物102的合成
(1)制备例1:化合物102的合成
将DMF(100mL)添加至中间体53-1(10g,0.025mol)、2-(4-溴苯基)吡啶(7.0g,0.030mol,TCI)、碳酸钾(6.89g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.9g,0.003mol,Sigma-Aldrich)和Cu(3.17g,0.050mol,Sigma-Aldrich)。在160℃下将混合物在搅拌下回流8小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供10.3g(产率74.6%)化合物102。
H-NMR(200MHz,CDCl3):δppm,1H(8.50/d,8.18/d,8.00/d,7.87/d,7.69/d,7.51/m,7.26/d,7.00/m),2H(8.30/d,7.77/s,7.71/d)4H(7.74/m,7.39/d)
LC/MS:m/z=554[(M+1)+]
合成例7:化合物140的合成
(1)制备例1:化合物140的合成
将DMF(100mL)添加至中间体53-1(10g,0.025mol)、2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪(11.6g,0.030mol,TCI)、碳酸钾(6.89g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.9g,0.003mol,Sigma-Aldrich)和Cu(3.17g,0.050mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流8小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供14.6g(产率82.7%)化合物140。
H-NMR(200MHz,CDCl3):δppm,1H(8.18/d,8.00/d,7.87/d,7.69,d),2H(7.79/d,7.77/s,7.68/d,7.41/m)4H(8.28/d,7.74/m,7.51/m,7.39/d)
LC/MS:m/z=708[(M+1)+]
合成例8:化合物147的合成
(1)制备例1:中间体147-1的合成
将THF(100ml)、乙醇(25ml)和H2O(25ml)添加至1-溴-4-碘苯(10g,0.035mol,Sigma-Aldrich)、苯并[d]唑-2-基硼酸(6.91g,0.042mol,mascot)、碳酸钾(9.77g,0.071mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.23g,0.001mol,Sigma-Aldrich)。在90℃下将混合物在搅拌下回流12小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供5.5g(产率56.8%)中间体147-1。
(3)制备例2:化合物147的合成
将DMF(100mL)添加至中间体53-1(10g,0.025mol)、中间体147-1(8.2g,0.044mol)、碳酸钾(6.89g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.90g,0.003mol,Sigma-Aldrich)和Cu(4.38g,0.069mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供9.7g(产率65.5%)化合物147。
H-NMR(200MHz,CDCl3):δppm,1H(8.18/d,8.00/d,7.87/d,7.69/d),2H(7.79/d,7.68/d),6H(7.74/m,7.39/d)
LC/MS:m/z=594[(M+1)+]
合成例9:化合物184的合成
(1)制备例1:中间体184-1的合成
将THF(100mL)、乙醇(25mL)和H2O(25mL)添加至3,6-二溴-9H-咔唑(10g,0.031mol,Sigma-Aldrich)、6-苯基苯并[d]噻唑-2-基硼酸(17.3g,0.068mol,mascot)、碳酸钾(17.01g,0.123mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.78g,0.001mol,Sigma-Aldrich)。在90℃下将混合物在搅拌下回流11小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供11.4g(产率63.3%)中间体184-1。
(2)制备例2:中间体184-2的合成
将THF(100mL)、乙醇(25mL)和H2O(25mL)添加至1-溴-4-碘苯(10g,0.035mol,Sigma-Aldrich)、苯并[d]噻唑-2-基硼酸(7.59g,0.042mol,mascot)、碳酸钾(9.77g,0.071mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.23g,0.001mol,Sigma-Aldrich)。在90℃下将混合物在搅拌下回流12小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供6.1g(产率59.5%)中间体184-2。
(3)制备例3:化合物184的合成
将DMF(100mL)添加至中间体184-1(10g,0.017mol)、中间体184-2(5.9g,0.021mol)、碳酸钾(4.72g,0.034mol,Sigma-Aldrich)、二苯并-18-冠-6(0.62g,0.002mol,Sigma-Aldrich)和Cu(2.17g,0.034mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供9.4g(产率69.3%)化合物184。
H-NMR(200MHz,CDCl3):δppm,1H(8.01/d,8.00/d,7.87/d,7.69/d),2H(8.34/s,8.18/d,7.81/d,7.79/d,7.68/d,7.53/m,7.41/m)4H(7.77/s,7.52/d,7.51/m)
LC/MS:m/z=794[(M+1)+]
合成例10:化合物191的合成
(1)制备例1:中间体191-1的合成
将甲苯(100mL)、乙醇(25mL)和H2O(25mL)添加至3,6-二溴-9H-咔唑(10g,0.031mol,TCI)、苯并[d]噻唑-2-基硼酸(12.12g,0.068mol,Sigma-Aldrich)、碳酸钾(12.76g,0.092mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.07g,0.001mol,Sigma-Aldrich)。在100℃下将混合物在搅拌下回流5小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.4g(产率55.5%)中间体191-1。
(2)制备例2:中间体191-2的合成
将DMF(100mL)添加至中间体191-1(10g,0.023mol)、2,5-二溴-4-苯基吡啶(8.7g,0.028mol,mascot)、碳酸钾(6.38g,0.046mol,Sigma-Aldrich)、二苯并-18-冠-6(0.83g,0.002mol,Sigma-Aldrich)和Cu(2.93g,0.046mol,Sigma-Aldrich)。在160℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.4g(产率48.2%)中间体191-2。
(3)制备例3:化合物191的合成
将甲苯(100mL)、乙醇(25mL)和H2O(25mL)添加至中间体191-2(10g,0.015mol)、苯并[d]噻唑-2-基硼酸(5.92g,0.033mol,mascot)、碳酸钾(4.15g,0.030mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.04g,0.001mol,Sigma-Aldrich)。在90℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供5.7g(产率52.7%)化合物191。
H-NMR(200MHz,CDCl3):δppm,1H(8.90/s,8.00/d,7.87/d,7.70/s,7.69/d,7.41/m),2H(7.79/d,7.77/s,7.51/m),3H(8.01/d),4H(8.18/d),6H(7.53/m)
LC/MS:m/z=719[(M+1)+]
合成例11:化合物201的合成
(1)制备例1:化合物201的合成
将甲苯(100mL)、乙醇(25mL)和H2O(25mL)添加至3,6-二溴-9-苯基-9H-咔唑(10g,0.025mol,Sigma-Aldrich)、1-苯基-1H-苯并[d]咪唑-2-基硼酸(7.12g,0.030mol,mascot)、碳酸钾(13.78g,0.100mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.73g,0.001mol,Sigma-Aldrich)。在100℃下将混合物在搅拌下回流8小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供9.5g(产率60.7%)化合物201。
H-NMR(200MHz,CDCl3):δppm,1H(8.18/d,8.00/d,7.87/d,7.69/d),2H(8.56/d,7.77/s,7.59/d),3H(7.45/m),4H(7.22/m),6H(7.58/m,7.50/d)
LC/MS:m/z=719[(M+1)+]
合成例12:化合物280的合成
(1)制备例1:中间体280-1的合成
将甲苯(100mL)、乙醇(25mL)和H2O(25mL)添加至3,7-二溴-10H-吩嗪(10g,0.030mol,mascot)、苯并[d]唑-2-基硼酸(10.51g,0.065mol,mascot)、碳酸钾(16.21g,0.117mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(2.03g,0.002mol,Sigma-Aldrich)。在90℃下将混合物在搅拌下回流8小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.8g(产率63.7%)中间体280-1。
(2)制备例2:化合物280的合成
将DMF(100mL)添加至中间体280-1(10g,0.024mol)、4-溴联苯(6.7g,0.029mol,mascot)、碳酸钾(6.62g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.86g,0.002mol,Sigma-Aldrich)和Cu(3.05g,0.048mol,Sigma-Aldrich)。在160℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供10.4g(产率76.2%)化合物280。
H-NMR(200MHz,CDCl3):δppm,1H(7.41/m),2H(7.54/d,7.52/d,7.51/m,6.69/d,6.65/d),4H(7.74/m,7.39/d,7.26/d)
LC/MS:m/z=569[(M+1)+]
合成例13:化合物304的合成
(1)制备例1:中间体304-1的合成
将甲苯(100mL)、乙醇(25mL)、H2O(25mL)添加至3,7-二溴-10H-吩噻嗪(10g,0.030mol,mascot)、苯并[d]唑-2-基硼酸(10.04g,0.062mol,mascot)、碳酸钾(15.48g,0.112mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.94g,0.002mol,Sigma-Aldrich)。在100℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.9g(产率65.1%)中间体304-1。
(2)制备例2:化合物304的合成
将DMF(100mL)添加至中间体304-1(10g,0.023mol)、10-(4-溴苯基)-9,9-二甲基-9,10-二氢吖啶(10.08g,0.028mol,TCI)、碳酸钾(6.38g,0.050mol,Sigma-Aldrich)、二苯并-18-冠-6(0.83g,0.002mol,Sigma-Aldrich)和Cu(2.93g,0.047mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供12.40g(产率75.0%)化合物304。
H-NMR(200MHz,CDCl3):δppm,1H(),2H(7.26/d,7.21/d,7.13/s,7.05/d,7.02/m,6.73/m,6.55/d,1.72/m),4H(7.74/m,7.39/d,6.38/d)
LC/MS:m/z=716[(M+1)+]
合成例14:化合物330的合成
(1)制备例1:中间体330-1的合成
将甲苯(100mL)、乙醇(25mL)和H2O(25mL)添加至2,7-二溴-9,10-二氢吖啶(10g,0.030mol,mascot)、6-苯基苯并[d]噻唑-2-基硼酸(16.55g,0.065mol,mascot)、碳酸钾(16.31g,0.118mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(0.37g,0.003mol,Sigma-Aldrich)。在100℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供10.7g(产率60.5%)中间体330-1。
(2)制备例2:化合物330的合成
将DMF(100mL)添加至中间体330-1(10g,0.017mol)、中间体184-2(5.8g,0.020mol)、碳酸钾(4.67g,0.033mol,Sigma-Aldrich)、二苯并-18-冠-6(0.60g,0.002mol,Sigma-Aldrich)和Cu(2.12g,0.033mol,Sigma-Aldrich)。在150℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供9.8g(产率72.7%)化合物330。
H-NMR(200MHz,CDCl3):δppm,1H(8.18/d,8.01/d,3.81/s),2H(8.34/s,7.81/d,7.77/d,7.76/d,7.57/d,7.54/s,7.53/m,7.41/m,6.69/d,6.57/d),4H(7.52/d,7.51/m)
LC/MS:m/z=808[(M+1)+]
合成例15:化合物349的合成
(1)制备例1:中间体349-1的合成
将甲苯(100mL)、乙醇(25mL)和H2O(25mL)添加至2,7-二溴-9,10-二氢吖啶(10g,0.427mol,mascot)、苯并[d]唑-2-基硼酸(9.77g,0.060mol,mascot)、碳酸钾(15.10g,0.110mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(1.89g,0.002mol,Sigma-Aldrich)。在100℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.6g(产率64.4%)中间体349-1。
(2)制备例2:中间体349-2的合成
将DMF(100mL)添加至中间体349-1(10g,0.023mol)、5-溴-2-碘吡啶(7.7g,0.027mol,mascot)、碳酸钾(6.23g,0.045mol,Sigma-Aldrich)、二苯并-18-冠-6(0.81g,0.002mol,Sigma-Aldrich)和Cu(2.87g,0.045mol,Sigma-Aldrich)。在160℃下将混合物在搅拌下回流7小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供6.7g(产率48.5%)中间体349-2。
(3)制备例3:化合物349的合成
将甲苯(100mL)、乙醇(25mL)和H2O(25mL)添加至中间体349-2(10g,0.017mol)、1-苯基-1H-苯并[d]咪唑-2-基硼酸(4.77g,0.020mol,mascot)、碳酸钾(4.61g,0.033mol,Sigma-Aldrich)和作为催化剂的Pd(PPh3)4(0.59g,0.005mol,Sigma-Aldrich)。在100℃下将混合物在搅拌下回流8小时。在反应完成之后,对反应混合物进行萃取并通过柱色谱法纯化以提供7.8g(产率65.6%)化合物349。
H-NMR(200MHz,CDCl3):δppm,1H(8.56/d,8.33/s,7.66/d,7.59/d,7.45/m,6.76/d),2H(7.61/s,7.58/m,7.50/d,7.22/m,6.61/d),4H(7.74/m,7.39/d)
LC/MS:m/z=712[(M+1)+]
装置实施例(主体)
将尺寸为25mm×25mm×0.7mm的ITO透明电极附接至玻璃基底,图案化为具有2mm×2mm的发光面积,接着进行清洁。在将基底安装在真空室中之后,将基础压力调节为≥1×10-6托。其后,在ITO基底上沉积有机材料和金属以制造具有以下结构的装置:
ITO/空穴注入层(HAT-CN,5nm)/空穴传输层(α-NPB,100nm)/发光层(20nm)/电子传输层(201:Liq,30nm)/LiF(1nm)/Al(100nm)
实施例1至7
将表1中示出的相应主体化合物2用于发光层来制造绿色有机电致发光装置。测量装置的发光特性(包括电流效率)。
具体地,使用HAT-CN在ITO透明电极上形成5nm厚的空穴注入层。其后,使用α-NPB形成空穴传输层。使用作为主体化合物1的GH1与表1中示出的相应主体化合物2的1∶1混合物形成20nm厚的发光层。使用Ir(ppy)3作为掺杂剂化合物。使用掺杂有Liq(50%)的式201的化合物形成30nm厚的电子传输层。随后,依次形成1nm厚的LiF层和100nm厚的铝层,完成有机电致发光装置的制造。
比较例1
以与实施例1至7中相同的方式制造有机电致发光装置,不同之处在于使用GH2作为主体材料2代替本发明的化合物形成发光层。
实验例1:实施例1至7中制造的装置的发光特性
使用源表(Model 237,Keithley)和分光辐射度计(PR-650,Photo Research)在10,000尼特下测量实施例1至7和比较例1中制造的有机电致发光装置的驱动电压、电流效率和色坐标。结果示于表1中。
表1
从表1中的结果可以看出,实施例1至7的装置(其中每一个都采用本发明的化合物作为用于发光层的主体化合物2)在较低的电压下驱动并且电流效率比比较例1的装置高。
装置实施例(覆盖层)
将尺寸为25mm×25mm×0.7mm的含有Ag的ITO透明电极附接至玻璃基底,图案化为具有2mm×2mm的发光面积,接着进行清洁。在将基底安装在真空室中后,将基础压力调节为1×10-6托。其后,在含有Ag的ITO玻璃基底上沉积有机材料和金属以制造具有以下结构的装置:
Ag:ITO/空穴注入层(HAT-CN,5nm)/空穴传输层(α-NPB,100nm)/电子阻挡层(TCTA,10nm)/发光层(20nm)/电子传输层(201:Liq,30nm)/LiF(1nm)/Mg:Ag(15nm)/覆盖层(70nm)
实施例8至15
使用表2中示出的相应的本发明的化合物作为用于覆盖层的材料来制造蓝色有机电致发光装置。测量有机电致发光装置的发光特性,包括发光效率。
具体地,将含有Ag的ITO透明电极设置在玻璃基底上,并且使用HAT-CN以在ITO透明电极上形成5nm厚的空穴注入层。其后,使用α-NPB形成100nm厚的空穴传输层。使用TCTA形成10nm厚的电子阻挡层。使用BH1作为主体化合物以及使用BD1作为掺杂剂化合物形成20nm厚的发光层。使用掺杂有Liq(50%)的式201的化合物形成30nm厚的电子传输层。形成1nm厚的LiF层。随后,形成15nm厚的Mg:Ag(1:9)层。使用表2中示出的相应的本发明的化合物形成70nm厚的覆盖层,完成有机电致发光装置的制造。
比较例2
以与实施例8至15中相同的方式制造有机电致发光装置,不同之处在于未使用覆盖层。
比较例3
以与实施例8至15中相同的方式制造有机电致发光装置,不同之处在于使用Alq3代替本发明的化合物形成覆盖层。
实验例2:实施例8至15中制造的装置的发光特性
使用源表(Model 237,Keithley)和分光辐射度计(PR-650,Photo Research)在1,000尼特下测量实施例8至15以及比较例2和3中制造的有机电致发光装置的驱动电压、电流效率和色坐标。结果示于表2中。
表2
从表2中的结果可以看出,实施例8至15的装置(其中使用本发明的化合物形成覆盖层)在较低的电压下驱动并且电流效率比比较例2和3的装置高。
Claims (8)
1.一种由式I表示的有机电致发光化合物:
其中X1和X2各自独立地为O、S或NR9,Y为单键、O、S、CR10R11或NR12,R9至R12各自独立地选自氢、氘、经取代或未经取代的C1至C10烷基、经取代或未经取代的C6至C30芳基、经取代或未经取代的C3至C30杂芳基、与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C6至C30芳基、和与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C3至C30杂芳基,R1至R8各自独立地选自氢、氘、卤素基团、氰基、经取代或未经取代的C1至C10烷基、经取代或未经取代的C6至C30芳基、经取代或未经取代的C3至C30杂芳基、与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C6至C30芳基、和与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C3至C30杂芳基,条件是R1至R8任选地彼此键合或者与一个或更多个相邻取代基连接而形成碳原子任选地经选自氮(N)原子、硫(S)原子和氧(O)原子的一个或更多个杂原子取代的至少一个脂环族或芳族的单环或多环,L为单键或者选自经取代或未经取代的C6至C30亚芳基和经取代或未经取代的C3至C30亚杂芳基,n为0至3的整数,Ar选自经取代或未经取代的C6至C30芳基、经取代或未经取代的C3至C30杂芳基、经取代或未经取代的芴基、与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C6至C30芳基、和与一个或更多个经取代或未经取代的C3至C20环烷基稠合的经取代或未经取代的C3至C30杂芳基,以及m为1至3的整数。
2.根据权利要求1所述的有机电致发光化合物,其中R1至R12、L和Ar的定义中的“经取代”表示经选自氘、卤素基团、氰基、硝基、羟基、甲硅烷基、烷基、环烷基、烷氧基、烯基、芳基、和杂环基、或者这些取代基中的两者或更多者的组合的一个或更多个取代基取代,以及相同定义中的“未经取代的”表示不具有取代基。
4.一种有机电致发光装置,包括第一电极、第二电极、和布置在所述第一电极与所述第二电极之间的一个或更多个有机层,其中所述有机层中的一个或更多个包含根据权利要求1所述的由式I表示的有机电致发光化合物。
5.根据权利要求4所述的有机电致发光装置,其中所述有机层包括选自空穴注入层、空穴传输层、兼具空穴注入功能和空穴传输功能的层、电子传输层、兼具电子传输功能和电子注入功能的层、电子阻挡层、空穴阻挡层、覆盖层和发光层的一个或更多个层,并且所述有机层中的一个或更多个包含所述由式I表示的有机电致发光化合物。
6.根据权利要求5所述的有机电致发光装置,其中所述发光层包含一种或更多种主体化合物,所述主体化合物之一为所述由式I表示的有机电致发光化合物。
7.根据权利要求5所述的有机电致发光装置,其中所述覆盖层形成在所述第一电极和所述第二电极的与所述有机层相对的上侧和下侧中的至少一者处,并且所述覆盖层包含所述由式I表示的有机电致发光化合物。
8.根据权利要求7所述的有机电致发光装置,其中所述覆盖层形成在所述第一电极的下侧或所述第二电极的上侧中的至少一者处。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020190063298A KR102080737B1 (ko) | 2019-05-29 | 2019-05-29 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
KR10-2019-0063298 | 2019-05-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN112010840A true CN112010840A (zh) | 2020-12-01 |
CN112010840B CN112010840B (zh) | 2024-04-26 |
Family
ID=69637233
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910807504.7A Active CN112010840B (zh) | 2019-05-29 | 2019-08-29 | 有机电致发光化合物和包含其的有机电致发光装置 |
Country Status (3)
Country | Link |
---|---|
US (1) | US11629142B2 (zh) |
KR (1) | KR102080737B1 (zh) |
CN (1) | CN112010840B (zh) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112300143A (zh) * | 2019-07-30 | 2021-02-02 | 江苏三月光电科技有限公司 | 一种基于咔唑为核心的有机化合物及其应用 |
CN112300146A (zh) * | 2019-07-30 | 2021-02-02 | 江苏三月科技股份有限公司 | 一种以咔唑为核心的有机化合物及包含其的有机电致发光器件 |
CN112300144A (zh) * | 2019-07-30 | 2021-02-02 | 江苏三月光电科技有限公司 | 一种基于咔唑为核心的有机化合物及其在oled上的应用 |
CN112851649A (zh) * | 2019-11-28 | 2021-05-28 | 南京高光半导体材料有限公司 | 一种含有多元杂环结构的有机电致发光化合物及有机电致发光器件和应用 |
CN113845514A (zh) * | 2021-11-01 | 2021-12-28 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
CN114230564A (zh) * | 2021-11-02 | 2022-03-25 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
WO2022148197A1 (zh) * | 2021-01-07 | 2022-07-14 | 陕西莱特光电材料股份有限公司 | 一种有机化合物以及使用其的电子元件和电子装置 |
CN115160304A (zh) * | 2022-06-16 | 2022-10-11 | 安徽秀朗新材料科技有限公司 | 一种咔唑类衍生物生产工艺 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20210111971A (ko) * | 2020-03-04 | 2021-09-14 | 덕산네오룩스 주식회사 | 광효율 개선층을 포함하는 유기전기소자 및 이를 포함하는 전자 장치 |
JPWO2022118910A1 (zh) * | 2020-12-02 | 2022-06-09 | ||
KR102356004B1 (ko) * | 2020-12-08 | 2022-02-07 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
CN116917292A (zh) * | 2021-08-04 | 2023-10-20 | 株式会社Lg化学 | 新的化合物和包含其的有机发光器件 |
KR20230025723A (ko) | 2021-08-12 | 2023-02-23 | 주식회사 랩토 | 시아노기가 치환된 카바졸 유도체 및 이를 포함한 유기전계발광소자 |
KR20230108770A (ko) * | 2022-01-10 | 2023-07-19 | 삼성디스플레이 주식회사 | 발광 소자 및 이를 포함한 전자 장치 |
KR20230131993A (ko) | 2022-03-07 | 2023-09-15 | 주식회사 랩토 | 카바졸 유도체 및 이를 포함한 유기전계발광소자 |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030129448A1 (en) * | 2001-10-19 | 2003-07-10 | Lightronik Technology Inc. | Organic EL device |
KR20130118269A (ko) * | 2012-04-19 | 2013-10-29 | 에스에프씨 주식회사 | 방향족 화합물 및 이를 포함하는 유기전계발광소자 |
CN103804372A (zh) * | 2012-11-08 | 2014-05-21 | 海洋王照明科技股份有限公司 | 双极性蓝光磷光化合物及其制备方法和应用 |
CN104471021A (zh) * | 2012-06-04 | 2015-03-25 | 株式会社P&Htech | 新的有机电致发光器件用化合物及包含该化合物的有机电致发光器件 |
CN104650066A (zh) * | 2014-08-05 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | 一种绿光材料的制备及其有机发光器件 |
CN104650067A (zh) * | 2014-08-05 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | 一种绿光材料及其制备方法和应用 |
CN104650855A (zh) * | 2014-08-15 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | 含三元咪唑并咔唑类衍生物的制备及其有机发光器件 |
KR20170063411A (ko) * | 2015-11-30 | 2017-06-08 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
KR20170094714A (ko) * | 2016-02-11 | 2017-08-21 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
CN108218867A (zh) * | 2017-12-01 | 2018-06-29 | 阜阳欣奕华材料科技有限公司 | 一种化合物、有机电致发光器件及显示装置 |
KR20190035070A (ko) * | 2017-09-26 | 2019-04-03 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5479759B2 (ja) * | 2008-09-05 | 2014-04-23 | 株式会社半導体エネルギー研究所 | ベンゾオキサゾール誘導体、発光素子用材料、発光素子、発光装置及び電子機器 |
KR20130143034A (ko) * | 2010-09-16 | 2013-12-30 | 닛토덴코 가부시키가이샤 | 유기 발광 소자에 사용하기 위한 치환된 비피리딘 |
US9353085B2 (en) * | 2011-08-26 | 2016-05-31 | E-Ray Optoelectronics Technology Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent devices using the same |
KR102411748B1 (ko) * | 2014-03-17 | 2022-06-23 | 롬엔드하스전자재료코리아유한회사 | 전자 버퍼 재료 및 유기 전계 발광 소자 |
KR20170030427A (ko) * | 2015-09-09 | 2017-03-17 | 주식회사 엘지화학 | 유기전계발광소자 |
KR102164767B1 (ko) * | 2016-04-12 | 2020-10-14 | 주식회사 엘지화학 | 유기화합물을 포함하는 캡핑층 및 이를 포함한 유기전계발광소자 |
-
2019
- 2019-05-29 KR KR1020190063298A patent/KR102080737B1/ko active IP Right Grant
- 2019-08-29 CN CN201910807504.7A patent/CN112010840B/zh active Active
-
2020
- 2020-03-13 US US16/817,820 patent/US11629142B2/en active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030129448A1 (en) * | 2001-10-19 | 2003-07-10 | Lightronik Technology Inc. | Organic EL device |
KR20130118269A (ko) * | 2012-04-19 | 2013-10-29 | 에스에프씨 주식회사 | 방향족 화합물 및 이를 포함하는 유기전계발광소자 |
CN104471021A (zh) * | 2012-06-04 | 2015-03-25 | 株式会社P&Htech | 新的有机电致发光器件用化合物及包含该化合物的有机电致发光器件 |
CN103804372A (zh) * | 2012-11-08 | 2014-05-21 | 海洋王照明科技股份有限公司 | 双极性蓝光磷光化合物及其制备方法和应用 |
CN104650066A (zh) * | 2014-08-05 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | 一种绿光材料的制备及其有机发光器件 |
CN104650067A (zh) * | 2014-08-05 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | 一种绿光材料及其制备方法和应用 |
CN104650855A (zh) * | 2014-08-15 | 2015-05-27 | 吉林奥来德光电材料股份有限公司 | 含三元咪唑并咔唑类衍生物的制备及其有机发光器件 |
KR20170063411A (ko) * | 2015-11-30 | 2017-06-08 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
KR20170094714A (ko) * | 2016-02-11 | 2017-08-21 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 전자 소자 |
KR20190035070A (ko) * | 2017-09-26 | 2019-04-03 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
CN108218867A (zh) * | 2017-12-01 | 2018-06-29 | 阜阳欣奕华材料科技有限公司 | 一种化合物、有机电致发光器件及显示装置 |
Non-Patent Citations (4)
Title |
---|
AHN, YEONSEON等: "Electroluminescence characteristics of a new green-emitting phenylphenothiazine derivative with phenylbenzimidazole substituent", 《BULLETIN OF THE KOREAN CHEMICAL SOCIETY》 * |
CHEN, HSIAO-FAND等: "Carbazole and benzimidazole/oxadiazole hybrids as bipolar host materials for sky blue, green, and red PhOLEDs", 《ORGANIC ELECTRONICS》 * |
STN: "《STN》", 11 October 2022 * |
ZHAO GAO: "High-efficiency deep blue fluorescent emitters based on phenanthro[9,10-d]imidazole substituted carbazole and their applications in organic light emitting diodes", 《ORGANIC ELECTRONICS》 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112300143B (zh) * | 2019-07-30 | 2022-08-16 | 江苏三月科技股份有限公司 | 一种基于咔唑为核心的有机化合物及其应用 |
CN112300146A (zh) * | 2019-07-30 | 2021-02-02 | 江苏三月科技股份有限公司 | 一种以咔唑为核心的有机化合物及包含其的有机电致发光器件 |
CN112300144A (zh) * | 2019-07-30 | 2021-02-02 | 江苏三月光电科技有限公司 | 一种基于咔唑为核心的有机化合物及其在oled上的应用 |
CN112300143A (zh) * | 2019-07-30 | 2021-02-02 | 江苏三月光电科技有限公司 | 一种基于咔唑为核心的有机化合物及其应用 |
CN112300144B (zh) * | 2019-07-30 | 2023-04-07 | 江苏三月科技股份有限公司 | 一种基于咔唑为核心的有机化合物及其在oled上的应用 |
CN112851649A (zh) * | 2019-11-28 | 2021-05-28 | 南京高光半导体材料有限公司 | 一种含有多元杂环结构的有机电致发光化合物及有机电致发光器件和应用 |
CN112851649B (zh) * | 2019-11-28 | 2023-09-29 | 南京高光半导体材料有限公司 | 一种含有多元杂环结构的有机电致发光化合物及有机电致发光器件和应用 |
WO2022148197A1 (zh) * | 2021-01-07 | 2022-07-14 | 陕西莱特光电材料股份有限公司 | 一种有机化合物以及使用其的电子元件和电子装置 |
CN113845514A (zh) * | 2021-11-01 | 2021-12-28 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
CN113845514B (zh) * | 2021-11-01 | 2024-07-05 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
CN114230564A (zh) * | 2021-11-02 | 2022-03-25 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
CN114230564B (zh) * | 2021-11-02 | 2024-06-04 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
CN115160304A (zh) * | 2022-06-16 | 2022-10-11 | 安徽秀朗新材料科技有限公司 | 一种咔唑类衍生物生产工艺 |
Also Published As
Publication number | Publication date |
---|---|
US11629142B2 (en) | 2023-04-18 |
CN112010840B (zh) | 2024-04-26 |
US20200377492A1 (en) | 2020-12-03 |
KR102080737B1 (ko) | 2020-02-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN112010840B (zh) | 有机电致发光化合物和包含其的有机电致发光装置 | |
KR102210267B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
US20230150992A1 (en) | Organic Light Emitting Compound And Organic Light Emitting Device Including Same | |
KR20210089294A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20210090389A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR102144164B1 (ko) | 유기 전계 발광 소자 | |
KR20210072660A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
CN110520427B (zh) | 新型杂环化合物及利用其的有机发光元件 | |
KR20210048018A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20190141598A (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
KR102356004B1 (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20210008218A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220009035A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220005264A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220004334A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220098455A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20210105042A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220084564A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220100224A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220003680A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220101829A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220098887A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220094825A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220090830A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 | |
KR20220055040A (ko) | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |