CN113594395A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
- Publication number
- CN113594395A CN113594395A CN202110990159.2A CN202110990159A CN113594395A CN 113594395 A CN113594395 A CN 113594395A CN 202110990159 A CN202110990159 A CN 202110990159A CN 113594395 A CN113594395 A CN 113594395A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- group
- organic electroluminescent
- electroluminescent device
- 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
- 230000005525 hole transport Effects 0.000 claims abstract description 46
- 239000010410 layer Substances 0.000 claims description 210
- 150000001875 compounds Chemical class 0.000 claims description 143
- -1 pentadeuterophenyl Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000001624 naphthyl group Chemical group 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 23
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 239000012044 organic layer Substances 0.000 claims description 20
- 125000000732 arylene group Chemical group 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000005549 heteroarylene group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 13
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000003944 tolyl group Chemical group 0.000 claims description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000005561 phenanthryl group Chemical group 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000005580 triphenylene group Chemical group 0.000 claims description 11
- 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 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 8
- 125000001725 pyrenyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000005567 fluorenylene group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000005551 pyridylene group Chemical group 0.000 claims description 4
- 125000006836 terphenylene group Chemical group 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 3
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 3
- 125000005558 triazinylene group Chemical group 0.000 claims description 3
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 150000005041 phenanthrolines Chemical class 0.000 claims description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 150000001616 biphenylenes Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 150000002979 perylenes Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 49
- 239000010409 thin film Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 238000000605 extraction Methods 0.000 abstract description 4
- 239000000969 carrier Substances 0.000 abstract description 2
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 108091008695 photoreceptors Proteins 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 74
- 238000003786 synthesis reaction Methods 0.000 description 73
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- 238000004128 high performance liquid chromatography Methods 0.000 description 46
- 238000001819 mass spectrum Methods 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 34
- 238000002347 injection Methods 0.000 description 32
- 239000007924 injection Substances 0.000 description 32
- 239000000543 intermediate Substances 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- 125000003118 aryl group Chemical group 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 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 6
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- JTWMOWRMSZZHDR-UHFFFAOYSA-N 7-(5-hydroxy-2-methylphenyl)-6-(2-methoxyphenyl)-4-methylpurino[7,8-a]imidazole-1,3-dione Chemical compound COC1=CC=CC=C1N(C(=CN12)C=3C(=CC=C(O)C=3)C)C2=NC2=C1C(=O)NC(=O)N2C JTWMOWRMSZZHDR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 150000003613 toluenes Chemical class 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000005956 isoquinolyl group Chemical group 0.000 description 3
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910000846 In alloy Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- NDBCGHNTWCYIIU-UHFFFAOYSA-N iridium(3+);1-phenylisoquinoline Chemical compound [Ir+3].[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12.[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12.[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12 NDBCGHNTWCYIIU-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 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 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical group C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- AJZDHLHTTJRNQJ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(tetrazol-1-yl)ethyl]benzamide Chemical compound N1(N=NN=C1)CCNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O AJZDHLHTTJRNQJ-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical group C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 1
- GWNJZSGBZMLRBW-UHFFFAOYSA-N 9,10-dinaphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 GWNJZSGBZMLRBW-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- ZPHQFGUXWQWWAA-UHFFFAOYSA-N 9-(2-phenylphenyl)carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 ZPHQFGUXWQWWAA-UHFFFAOYSA-N 0.000 description 1
- DVNOWTJCOPZGQA-UHFFFAOYSA-N 9-[3,5-di(carbazol-9-yl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 DVNOWTJCOPZGQA-UHFFFAOYSA-N 0.000 description 1
- HTJPPQKJCPTAED-UHFFFAOYSA-N 9-n,10-n-bis(4-methylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC(C)=CC=2)=C2C=CC=CC2=1)C1=CC=CC=C1 HTJPPQKJCPTAED-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 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
- 229940126062 Compound A Drugs 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 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
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- RWQJLIWMOBYOTI-AWEZNQCLSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyridin-3-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=CC=1 RWQJLIWMOBYOTI-AWEZNQCLSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 description 1
- IBTCZUXKFPQNMB-UHFFFAOYSA-N [B].OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.[Li] Chemical compound [B].OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.[Li] IBTCZUXKFPQNMB-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 125000005571 adamantylene group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-N aluminum;2-methylquinolin-8-ol;4-phenylphenol 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-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol 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-N 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 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
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K50/15—Hole transporting layers
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic electroluminescent device, and relates to the technical field of organic electroluminescence. The organic electroluminescent device comprises a hole transport layer, an electron transport layer and an optional covering layer. The specific hole transport layer material and the specific electron transport layer material are matched and applied to the organic electroluminescent device, so that the transport efficiency of holes and electrons in the device is improved, the maximum combination of current carriers is realized, the luminous efficiency of the organic electroluminescent device is improved, and the driving voltage of the device can be reduced; in addition, the use of the covering layer material is increased, the total reflection loss and the waveguide loss in the OLED device are effectively reduced, and the light extraction efficiency is improved, so that the luminous efficiency of the organic electroluminescent device is better improved, and the organic electroluminescent device has good application effect and industrialization prospect. The organic light emitting diode can be widely applied to the fields of panel display, lighting sources, organic solar cells, organic photoreceptors or organic thin film transistors and the like.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device.
Background
As a novel display technology, the organic electroluminescent device has the unique advantages of self luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide applicable temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, and can be applied to flat panel displays and new generation illumination.
An organic electroluminescent device (OLED) is a device prepared by depositing one or more layers of organic materials between a cathode and an anode by spin coating or vacuum evaporation. The organic electroluminescent device has the light emitting principle that when voltage is applied to the anode and the cathode, the two electrodes generate an electric field, under the action of the electric field, holes generated by the anode are combined with electrons generated by the cathode in the light emitting layer through the hole transport layer to form excitons, the excitons are in an excited state and release energy outwards, and the process of releasing energy from the excited state to a ground state releases energy and emits light outwards. Therefore, it is important to improve the recombination of electrons and holes in the OLED device.
OLED devices generally include an anode, a cathode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), a capping layer (CPL), and the like. Generally, the hole mobility of the hole transport material is often greater than the electron mobility of the electron transport material, so that the injection of holes and electrons is unbalanced, and the two cannot be effectively combined in the light emitting layer, resulting in a reduction in the light emitting efficiency of the organic light emitting device. In addition, when the OLED device is operated by applying voltage, Joule heat can be generated, so that organic materials are easy to crystallize, and the service life and the efficiency of the device are influenced. Due to the huge difference between the external quantum efficiency and the internal quantum efficiency of the OLED, the development of the OLED is greatly restricted.
Total reflection occurs at the interface between the ITO thin film and the glass substrate and the interface between the glass substrate and the air, the light emitted to the front external space of the OLED device accounts for about 20% of the total amount of the organic material thin film EL, and the remaining about 80% of the light is mainly confined in the organic material thin film, the ITO thin film and the glass substrate in the form of a waveguide. It can be seen that the light extraction efficiency of the conventional OLED device is low (about 20%), which severely restricts the development and application of the OLED. How to reduce the total reflection effect in the OLED device and improve the ratio of light coupled to the forward external space of the device (light extraction efficiency) has attracted much attention.
Therefore, how to combine and adjust various materials to make an organic electroluminescent device so that the organic electroluminescent device can achieve the effects of reducing voltage, improving efficiency and prolonging service life is a problem to be solved by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide an organic electroluminescent device, which is intended to improve device characteristics of the organic electroluminescent device, in particular, to greatly improve light emission efficiency of the device and to reduce driving voltage of the device.
In order to achieve the above object, the present invention provides an organic electroluminescent device, and deeply evaluates the characteristics of the organic electroluminescent device, solving the above problems. The organic electroluminescent device comprises a substrate, an anode, an organic layer and a cathode, wherein the organic layer comprises a hole transport layer and an electron transport layer, the hole transport layer contains a triamine compound represented by a formula I, the electron transport layer contains a heterocyclic compound represented by a formula II,
wherein, in formula I, X is selected from O or S;
the A ring, the B ring or the C ring is independently selected from a benzene ring, a naphthalene ring or no;
the R groups are the same or different from each other and are independently selected from one of methyl, ethyl, phenyl, tolyl, pentadeuterophenyl and naphthyl, or two adjacent R groups can be bonded to form a cyclic structure;
ar is1、Ar2、Ar3、Ar4Independently selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
said L1、L2、L3、L4、L5、L6Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;
the R is1、R2Independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
in the formula II, R is0The two R are same or different from each other and are independently selected from one of methyl, ethyl, phenyl, tolyl, pentadeuterated phenyl and naphthyl, or two adjacent R0The group can be bonded with the connected segment to form a spirofluorene cyclic structure;
said X1To X5Are the same or different from each other and are each independently N or C (R)w) And at least one is N, when C (R)w) When there are plural, plural C (R)w) Are identical to or different from each other, wherein RwOne selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
Rx、Ry、Rzthe aryl group may be one or two groups, which may be the same or different from each other, independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, and a substituted or unsubstituted C2-C20 heteroaryl group, or two adjacent groups may be bonded to form a cyclic structure; x is 0, 1,2, 3 or 4; y is 0, 1,2, 3 or 4; z is 0, 1,2, 3 or 4;
l is selected from one of single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30;
n is 0, 1,2 or 3.
The invention has the beneficial effects that:
the invention provides an organic electroluminescent device comprising a hole transport layer, an electron transport layer and optionally a capping layer. The triamine compound represented by the formula I is applied to the hole transport layer, the heterocyclic compound represented by the formula II is applied to the electron transport layer, and the triamine compound and the heterocyclic compound are matched and applied to the organic electroluminescent device, so that the transmission efficiency of holes and electrons in the device is improved, the holes and the electrons are effectively blocked in the light-emitting layer, the maximum combination of carriers is realized, the light-emitting efficiency of the organic electroluminescent device is improved, and the driving voltage of the device can be reduced; in addition, the triarylamine compound represented by the formula III is applied to the covering layer, so that the total reflection loss and waveguide loss in the OLED device are effectively reduced, the light extraction efficiency is improved, and the luminous efficiency of the organic electroluminescent device is better improved.
The organic electroluminescent device prepared by the invention greatly improves the device characteristics, effectively improves the luminous efficiency of the organic electroluminescent device, reduces the driving voltage of the device, and has good application effect and industrialization prospect.
Detailed Description
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
The alkyl group in the present invention refers to a hydrocarbon group obtained by dropping one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group or a branched-chain alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like, but is not limited thereto; the branched alkyl group includes, but is not limited to, an isomeric group of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
The cycloalkyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a cycloalkane molecule, and preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms, and examples thereof may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, bornyl, norbornyl, and the like. The alkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group or a norbornyl group.
The aryl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule, and may be monocyclic aryl group, polycyclic aryl group or condensed ring aryl group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 14 carbon atoms. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, phenyl group and the like, but is not limited thereto; the polycyclic aromatic group means an aromatic group having two or more independent aromatic rings in the molecule, for example, biphenyl group, terphenyl group and the like, but is not limited thereto; the fused ring aryl group refers to an aryl group in which two or more aromatic rings are contained in a molecule and are fused together by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, and the like. The above aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthryl group (preferably a 2-anthryl group), a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylene group, or a spirobifluorenyl group.
The heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic nucleus carbon atoms in an aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen or phosphorus atom, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, wherein the linking site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl and the like, but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, phenylpyridyl, and the like, but is not limited thereto; the fused ring heteroaryl group includes quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl and the like, but is not limited thereto. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group or a phenoxathiyl group.
The arylene group of the present invention refers to the aromatic compound molecule which has two hydrogen atoms removed from the aromatic nucleus carbon and R is remainedxThe group, which may be a monocyclic arylene group, a polycyclic arylene group or a fused ring arylene group, has preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 14 carbon atoms. The monocyclic arylene group includes phenylene group and the like, but is not limited thereto; the polycyclic arylene group includes, but is not limited to, biphenylene, terphenylene, and the like; the condensed ring arylene group includes naphthylene, anthrylene, phenanthrylene, fluorenylene, pyrenylene, triphenylene, fluoranthenylene, phenylfluorenylene, and the like, but is not limited thereto. The arylene group is preferably a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, or a phenylfluorenylene group.
Heteroarylene as used herein refers to the generic term for groups in which one or more of the aromatic core carbons in the arylene group is replaced with a heteroatom, including, but not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, the linking site of the heteroarylene group may be located on a ring-forming carbon atom or on a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused ring heteroarylene group. The monocyclic heteroarylene group includes a pyridylene group, a pyrimidylene group, a triazinylene group, a furanylene group, a thiophenylene group and the like, but is not limited thereto; the polycyclic heteroarylene group includes bipyridyl idene, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroarylene group includes, but is not limited to, a quinolylene group, an isoquinolylene group, an indolyl group, a benzothiophene group, a benzofuranylene group, a benzoxazolyl group, a benzimidazolylene group, a benzothiazolyl group, a dibenzofuranylene group, a dibenzothiophenylene group, a carbazolyl group, a benzocarbazolyl group, an acridinylene group, a 9, 10-dihydroacridine group, a phenoxazinyl group, a phenothiazinylene group, a phenoxathiin group and the like. The heteroaryl group is preferably a pyridylene group, pyrimidylene group, thienylene group, furylene group, benzothienylene group, benzofuranylene group, benzoxazolyl group, benzimidazolylene group, benzothiazolyl group, dibenzofuranylene group, dibenzothiophenylene group, dibenzofuranylene group, carbazolyl group, acridinylene group, phenoxazinyl group, phenothiazinylene group, phenoxathiin group.
In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example,
can represent
The substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene of the present invention are meant to be independently substitutedSelected from deuterium group, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted amine group and the like, but is not limited thereto, and is preferably mono-or polysubstituted with a group selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, tolyl, mesityl, penta-deuterated phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, pyrenyl, benzyl, triphenylenyl and the like,
Mono-or polysubstituted with groups such as, for example, a phenyl group, a perylene group, a fluoranthenyl group, a fluorenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a spirobifluorenyl group, a dianilino group, a dimethylamino group, a carbazolyl group, a 9-phenylcarbazolyl group, a carbazolonyl group, a pyrrolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, an oxazolyl group, a thiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzotriazolyl group, a benzimidazolyl group, an indolyl group, a quinolyl group, an isoquinolyl group, a phenothiazinyl group, a phenoxazinyl group, an acridinyl group.
The bonding to form a cyclic structure according to the present invention means that the two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:
in the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a fused ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclopentane, cyclohexane-acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but not limited thereto.
The invention provides an organic electroluminescent device which comprises a substrate, an anode, an organic layer and a cathode, wherein the organic layer comprises a hole transport layer and an electron transport layer. Optionally, the organic electroluminescent device of the present invention further comprises a capping layer. The organic layer of the organic electroluminescent device of the present invention may be formed of a single layer structure or a multilayer structure in which the above organic layers are stacked; meanwhile, each of the organic layers may further include one or more layers, for example, the hole transport layer may include a first hole transport layer, a second hole transport layer, a third hole transport layer, and the like, and the electron transport layer may include a first electron transport layer, a second electron transport layer, and the like. Corresponding functional layers may be added or subtracted as desired.
The organic electroluminescent device of the present invention preferably has the following structure:
(1) anode/hole transport layer/light emitting layer/electron transport layer/cathode/capping layer;
(2) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
(3) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
(4) anode/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
(5) anode/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/cathode/capping layer;
(6) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode/capping layer;
(7) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode/capping layer;
(8) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
(9) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
(10) anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode/capping layer;
(11) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode/capping layer;
(12) anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
(13) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
(14) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/cathode/capping layer;
(15) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode/capping layer;
(16) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer.
However, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the parameter requirements of the device and the characteristics of materials, and part of organic layers can be added or omitted. For example, a hole buffer layer may be added between the hole transport layer and the hole injection layer, an electron buffer layer may be added between the electron transport layer and the electron injection layer, or an organic layer having the same function may be formed in a stacked structure of two or more layers.
The organic electroluminescent device of the present invention is generally formed on a substrate. A substrate may be used under the anode or over the cathode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. The substrate may be any substrate as long as it does not change when forming an electrode or an organic layer, for example, a substrate of glass, plastic, a polymer film, silicon, or the like. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.
In the organic electroluminescent device of the present invention, the anode material may be selected from metals, such as aluminum, copper, gold, silver, and the like,Iron, chromium, nickel, manganese, palladium, platinum, and the like, and alloys thereof; examples of the metal oxide include indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and tin dioxide (SnO)2) Aluminum zinc oxide, and the like; examples of the conductive polymer include polyaniline, polypyrrole, and poly (3-methylthiophene). In addition to the above materials and combinations thereof, the anode material may also include other known materials suitable for use as an anode.
In the organic electroluminescent device according to the present invention, the hole injection material may be a metal oxide such as molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, or titanium oxide, or a low molecular weight organic compound such as a phthalocyanine-based compound or a polycyano group-containing conjugated organic material, but is not limited thereto. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of H1 to H17 described below, or employ one or more compounds of P1 to P12; one or more compounds of H1-H17 can be also used for doping one or more compounds of the following P1-P12, preferably, the mode that one or more compounds of H1-H17 are used for doping one or more compounds of the following P1-P12 in the hole injection layer of the invention is adopted, and the host material is selected from one of the following compounds:
preferably, the doping material is selected from one of the following compounds represented by P1-P12:
in the organic electroluminescent device of the present invention, the hole transport layer material may be selected from small molecular materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, and the like, and polymer materials such as poly-p-phenylene derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, polysilane and its derivatives, but is not limited thereto. Preferably, the hole transport layer material of the present invention is selected from one or more mixtures of triamine compounds represented by the following formula i:
x is selected from O or S;
the A ring, the B ring or the C ring is independently selected from a benzene ring, a naphthalene ring or no;
the R groups are the same or different from each other and are independently selected from one of methyl, ethyl, phenyl, tolyl, pentadeuterophenyl and naphthyl, or two adjacent R groups can be bonded to form a cyclic structure;
ar is1、Ar2、Ar3、Ar4Independently selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
said L1、L2、L3、L4、L5、L6Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;
the R is1、R2Independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl.
Preferably, Ar is1、Ar2、Ar3、Ar4Independently selected from one of the following substituents:
the R is11Selected from deuterium, methyl, ethyl,One of n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, adamantyl, norbornyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl and pyrenyl;
h is 0, 1,2, 3 or 4; i is 0, 1,2, 3, 4 or 5; j is 0, 1,2, 3, 4, 5, 6 or 7; k is 0, 1,2, 3, 4, 5, 6, 7, 8 or 9.
Preferably, Ar is1、Ar2One selected from the following substituents:
more preferably, Ar1、Ar2One selected from the following substituents:
preferably, Ar is3、Ar4One selected from the following substituents:
preferably, said L1、L2、L3、L4、L5、L6Independently selected from one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene and substituted or unsubstituted fluorenylene, wherein the substituent of the substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene and substituted or unsubstituted fluorenylene is one or more of deuterium, methyl, ethyl, isopropyl, tertiary butyl, phenyl, biphenyl and pentadeuterated phenyl.
More preferably, said L1、L2、L3、L4、L5、L6Independently selected from a single bond or one of the following substituents:
preferably, the
One selected from the group shown below:
preferably, the
One selected from the group shown below:
preferably, said R is1、R2Independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, adamantyl, norbornyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl and 9-phenylcarbazolyl.
Most preferably, the triamine compound represented by the formula I is selected from any one of the following compounds:
in the organic electroluminescent device according to the present invention, the light-emitting layer material includes a light-emitting layer host material AND a light-emitting layer guest material, the light-emitting layer host material may be selected from 4,4 '-bis (9-Carbazole) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4',1 ″: 4", 1' "-tetrabiphenyl ] -4, 4' -diamino (4PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), and the like. In addition to the above materials and combinations thereof, the light-emitting layer host material may also include other known materials suitable for use as a light-emitting layer, such as red light-emitting layer host materials represented by RH-1 to RH-12 below:
the light-emitting layer guest can be selected from 9, 10-di [ N- (p-tolyl) anilino]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq)3) Bis (1-phenylisoquinoline) (acetylacetonato) iridium (Ir (piq))2(acac)) and the like. In addition to the above materials, the light-emitting layer guest material may include other known materials suitable for use as a light-emitting layer, such as red light-emitting layer guest materials as represented by RD-1 to RD-12 below:
the doping ratio of the host material and the guest material of the light-emitting layer may be preferably varied depending on the materials used, and the mass percentage of the guest material of the light-emitting layer is usually 0.01 to 20%, preferably 0.1 to 15%, and more preferably 1 to 10%.
In the organic electroluminescent device of the present invention, the electron transport material may be selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq)3) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), and the like, and the electron transport material may include other known materials suitable for an electron transport layer in addition to the above materials and combinations thereof. Preferably, the electron transport layer of the present invention and one or more mixtures containing heterocyclic compounds represented by the following formula II,
wherein, R is0The two R are same or different from each other and are independently selected from one of methyl, ethyl, phenyl, tolyl, pentadeuterated phenyl and naphthyl, or two adjacent R0The group can be bonded with the connected segment to form a spirofluorene cyclic structure;
said X1To X5Are the same or different from each other and are each independently N or C (R)w) And at least one is N, when C (R)w) When there are plural, plural C (R)w) Are identical to or different from each other, wherein RwOne selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
Rx、Ry、Rzthe aryl group may be one or two groups, which may be the same or different from each other, independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, and a substituted or unsubstituted C2-C20 heteroaryl group, or two adjacent groups may be bonded to form a cyclic structure; x is 0, 1,2, 3 or 4; y is 0, 1,2, 3 or 4; z is 0, 1,2, 3 or 4;
l is selected from one of single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30;
n is 0, 1,2 or 3.
Preferably, the
Is selected from one of the groups shown below,
z is1Is 0, 1,2 or 3; z is a radical of2Is 0, 1 or 2.
Preferably, said R isx、Ry、RzIdentical to or different from each other, each independently selected from hydrogen, deuterium, a halogen group, cyano, nitro, amino, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl or from one of the structures shown below,
preferably, said R isySelected from hydrogen, deuterium, a halogen group, cyano, nitro, amino, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, adamantyl, norbornyl or one of the structures shown below,
preferably, Rw is selected from one of hydrogen, deuterium, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, dibenzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, pyridyl, pyrimidyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthroline, dibenzofuranyl, dibenzothienyl, and carbazolyl.
Preferably, L is selected from the group consisting of a single bond, a substituted or unsubstituted cyclohexylene group, a substituted or unsubstituted adamantylene group, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted benzofluorenylene group, a substituted or unsubstituted dibenzofluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted isoquinolinylene group, Substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthroline, substituted or unsubstituted azaanthracylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, or substituted or unsubstituted carbazolyl.
Most preferably, the heterocyclic compound represented by the formula II is selected from any one of the following compounds:
in the organic electroluminescent device according to the present invention, the electron injection material may Be selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, lithium fluoride (LiF), sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, magnesium fluoride, calcium fluoride, lithium oxide, cesium carbonate, potassium silicate, lithium acetate, lithium tetrakis (8-hydroxyquinoline) boron, 8-hydroxyquinoline-lithium (Liq), and the like, and in addition to the above materials and combinations thereof, the electron injection material may include other known materials suitable for an electron injection layer. Preferably, the electron injection layer according to the present invention is selected from lithium fluoride (LiF), 8-hydroxyquinoline-lithium (Liq), and the like.
In the cathode material, a metal material having a small work function is generally preferable in order to inject electrons into the electron injection/transport layer or the light-emitting layer. For example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and the like, alloys of 2 or more of these metals, or alloys of 1 or more of these metals and 1 or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, or graphite intercalation compounds, and the like can be used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The cathode may have a laminated structure of 2 or more layers. In addition to the above materials and combinations thereof, the cathode material may also include other known materials suitable for use as a cathode.
Among them, when light emission of the light-emitting layer is extracted from the cathode, the light transmittance of the cathode is preferably more than 10%. It is also preferable that the sheet resistivity of the cathode is several hundred Ω/□ or less, and the film thickness is usually 10nm to 500nm, preferably 10nm to 100 nm.
In the organic electroluminescent device, the covering layer contains the triarylamine compound shown in the formula III, and the triarylamine compound can be independently formed into a film or can be mixed with other materials to form a film,
said XaSelected from O or S;
ar isa、ArbIndependently selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, with the proviso that AraOr ArbAt least one of them is a condensed ring group;
said La、Lb、LcIndependently selected from single bond, substituted or unsubstituted arylene of C6-C30, and substituted or unsubstituted heteroarylene of C3-C30One of (1);
the R isa、RbIndependently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl.
Preferably, Ar isaAnd (b) one selected from substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysenyl and substituted or unsubstituted perylene.
Preferably, Ar isaOne selected from the following substituents:
the R is31One selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, adamantyl, norbornyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl and phenanthryl;
a is 0, 1,2, 3 or 4; b is 0, 1,2, 3, 4, 5, 6 or 7; c is 0, 1,2, 3, 4, 5, 6, 7, 8 or 9; d is 0, 1,2, 3, 4, 5, 6, 7, 8, 9,10 or 11.
More preferably, Ar isaOne selected from the following substituents:
wherein Ad is adamantyl or norbornyl.
Preferably, Ar isbOne selected from the following substituents:
wherein Ad is adamantyl or norbornyl.
Preferably, said La、Lb、LcIndependently selected from a single bond or one of the bridging groups shown below:
more preferably, said La、Lb、LcIndependently selected from a single bond or one of the following groups:
preferably, said R isa、RbIndependently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, adamantyl, norbornyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene and pyrenyl.
Most preferably, the triarylamine compound represented by formula iii is selected from any one of the following compounds:
preferably, the refractive index range of the covering layer is 1.8-2.5, and the thickness of the covering layer is 40-80 nm.
More preferably, the refractive index of the covering layer ranges from 1.9 to 2.3, and the thickness of the covering layer ranges from 55nm to 70 nm.
The organic layer of the organic electroluminescent device of the present invention has a film thickness selected from the range of 0.5nm to 500nm, preferably 1nm to 300nm, and more preferably 1nm to 120 nm. The film thickness of the organic layer is appropriately changed depending on the kind of material used in the organic electroluminescent device and the thickness of the other layer.
The optimum film thicknesses of the hole transporting layer and the electron transporting layer may vary depending on the materials used, and may be selected so as to achieve appropriate values of the driving voltage and the light emission efficiency. Therefore, the thickness of the electron transport layer is, for example, 1nm to 1um, preferably 2nm to 500nm, and more preferably 5nm to 200 nm.
In the organic electroluminescent device of the present invention, at least one of the anode and the cathode is transparent or translucent, and preferably, the anode side is transparent or translucent.
The order and number of layers of the organic electroluminescent element and the thickness of each layer may be appropriately selected in consideration of the luminous efficiency and the lifetime of the element. The method for forming each layer in the organic electroluminescent device is not particularly limited, and any one of vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slit coating, and dip coating may be used, and in the present invention, vacuum evaporation is preferably used.
The organic electroluminescent device can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lamps and the like.
The triamine compound represented by the formula I, the heterocyclic compound represented by the formula II and the triarylamine compound represented by the formula III can be obtained by the following methods:
formula I is a reaction formula:
bromo-compound A-1 and arylamine compound B-1 are coupled and reacted through Buchwald-Hartwig to obtain intermediate C-1, and intermediate C-2 and intermediate C-3 are obtained in the same way; carrying out Buchwald-Hartwig coupling reaction on the compound D and the intermediate C-1 to obtain an intermediate E; the intermediate E and the intermediate C-2 obtain an intermediate F; and carrying out Buchwald-Hartwig coupling reaction on the intermediate F and the intermediate C-3 to finally obtain the target compound shown in the formula I.
The formula II is shown as the following reaction formula:
formula ii the formula ii can be prepared by coupling a halogen substituted heterocyclic compound with an aromatic compound substituted with a boronic acid or boronic acid derivative using a palladium catalysed reaction, the preparation being obtainable by a carbon coupling reaction and a Miyaura boronation reaction.
The Xn is selected from one of F, Cl, Br and I, and each Xn is the same or different; conventional methods well known to those skilled in the art may be employed. For example, carbon-carbon coupling reactions, Miyaura boronation reactions, and the like.
Formula III reaction formula:
performing Buchwald-Hartwig coupling reaction on the bromo-compound A ' and the arylamine compound B ' to obtain an intermediate D '; and (3) carrying out Buchwald-Hartwig coupling reaction on the intermediate D 'and the compound C', and finally obtaining the target compound shown in the formula III.
The sources of the raw materials used in the above-mentioned reactions are not particularly limited, and the triamine compounds represented by formula I, the heterocyclic compounds represented by formula II, and the triarylamine compounds represented by formula III according to the present invention can be obtained by using commercially available raw materials or by using preparation methods known to those skilled in the art. The present invention is not particularly limited to the above-mentioned reaction, and a conventional reaction known to those skilled in the art may be used.
The invention is explained in more detail by the following examples, without wishing to restrict the invention accordingly. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue inventive effort.
Description of raw materials, reagents and characterization equipment:
the raw materials used in the following examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art.
The mass spectra were obtained using a UK Watts G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer.
The elemental analysis was carried out by using a Vario EL cube type organic element analyzer of Elementar, Germany, and the sample mass was 5 to 10 mg.
Synthesis example 1: preparation of Compound 1-1
Synthesis of intermediate C-1
Compound A-1(22.40g,82mmol), B-1(7.64g,82mmol) and sodium tert-butoxide (14.13g,147mmol) were dissolved in 300ml of degassed toluene under argon, palladium acetate (0.64g,2.87mmol) and triphenylphosphine (0.75g,2.87mmol) were added with stirring, and the mixture of the above reactants was heated under reflux for 7 h. After the reaction is finished, cooling the reaction mixture to room temperature, adding 90ml of deionized water for washing, stirring, standing for liquid separation, repeating the operation for three times, concentrating the organic layer under reduced pressure to one third of the volume of the system, stirring for crystallization, filtering by a Buchner funnel, leaching by toluene, and purifying by silica gel column chromatography by using petroleum ether and dichloromethane of which the ratio is 3:1 as a mobile phase to obtain an intermediate C-1(19.89g and 85%), wherein the solid purity is not less than 99.7% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 285.1528 (theoretical value: 285.1517).
Synthesis of Compound 1-1
Intermediate C-2(16.85g,65mmol), D-1(14.68g,65mmol) and sodium tert-butoxide (11.24g,117mmol) were dissolved in 250ml of dehydrated toluene under argon and Pd (dba) was added with stirring2(1.31g,2.28mmol)，P(t-Bu)3(0.46g,2.28mmol), and the mixed solution of the above reactants was heated under reflux for 8 h. After the reaction is finished, cooling the reaction mixture to room temperature, adding 75ml of deionized water for washing, stirring, standing for liquid separation, repeating the operation for three times, concentrating the organic layer under reduced pressure to one third of the volume of the system, stirring for crystallization, filtering, eluting with toluene, and purifying by silica gel column chromatography with ethyl acetate, dichloromethane and mobile phase of 1:5 to obtain an intermediate E-1(22.60g, 86%), wherein the solid purity is not less than 99.4% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 403.0542 (theoretical value: 403.0531).
Intermediate E-1(20.21g,50mmol), C-1(14.23g,50mmol) and sodium tert-butoxide (8.65g,90mmol) were dissolved in 200ml of dehydrated toluene under argon, and Pd was added thereto with stirring2(dba)3(1.60g,1.75mmol), X-phos (0.83g,1.75mmol), and the mixed solution of the above reactants was heated under reflux for 8 h. After the reaction is finished, cooling to room temperature, adding 70ml of deionized water, stirring, washing, standing, separating liquid, repeating the operation for three times, concentrating the organic phase under reduced pressure to one third of the volume of the system, stirring and crystallizingFiltering, eluting with toluene, purifying by silica gel column chromatography with dichloromethane and n-heptane 1:3 as mobile phase, and then recrystallizing with toluene to obtain compound 1-1(37.89g, 84%), with solid purity ≧ 99.8% by HPLC. Mass spectrum m/z: 901.4078 (theoretical value: 901.4032). Theoretical element content (%) C66H51N3O: c, 87.87; h, 5.70; and N, 4.66. Measured elemental content (%): c, 87.82; h, 5.68; and N, 4.63.
Intermediates C-3 to C-6, C-9 to C-15, C-17 and C-18 can be prepared according to the preparation method of the intermediate C-1 in synthetic example 1 by correspondingly replacing the raw materials and the intermediates, and the yield is shown in the following table:
synthesis example 2: preparation of Compounds 1-15
By replacing C-2 in Synthesis example 1 with an equimolar amount of C-7 and replacing C-1 with an equimolar amount of C-8, and by following the same procedure, Compound 1-15(48.04g, 85%) was obtained, which had a solid purity of 99.3% or more by HPLC. Mass spectrum m/z: 1129.4923 (theoretical value: 1129.4971). Theoretical element content (%) C78H57N3O: c, 89.03; h, 5.46; and N, 3.99. Measured elemental content (%): c, 89.07; h, 5.45; and N, 3.94.
Synthetic example 3: preparation of Compounds 1-49
The C-2 in Synthesis example 1 was replaced with equimolar C-3, C-1The same procedure was repeated except for the formation of equimolar C-4 to give compounds 1-49(43.15g, 82%) having a purity of > 99.5% by HPLC. Mass spectrum m/z: 1051.4547 (theoretical value: 1051.4502). Theoretical element content (%) C78H57N3O: c, 89.03; h, 5.46; and N, 3.99. Measured elemental content (%): c, 89.07; h, 5.45; and N, 3.94.
Synthetic example 4: preparation of Compounds 1-95
By replacing C-2 in Synthesis example 1 with an equimolar amount of C-11 and replacing C-1 with an equimolar amount of C-12, and by following the same procedure, Compound 1-95(53.79g, 84%) was obtained, which had a solid purity of 99.5% or more by HPLC. Mass spectrum m/z: 1280.5423 (theoretical value: 1280.5474). Theoretical element content (%) C96H69N3O: c, 90.04; h, 5.43; and N, 3.28. Measured elemental content (%): c, 90.07; h, 5.40; and N, 3.24.
Synthesis example 5: preparation of Compounds 1-216
Synthesis example 1 was repeated in the same manner except for replacing C-2 with equimolar C-15 to give compounds 1 to 216(40.47g, 85%) having a solid purity of 99.8% by HPLC. Mass spectrum m/z: 951.4175 (theoretical value: 951.4189). Theoretical element content (%) C70H53N3O: c, 88.30; h, 5.61; n, 4.41. Measured elemental content (%): c, 88.25; h, 5.64; n, 4.44.
Synthetic example 6: preparation of Compounds 1-265
Compound C-1(19.98g,70mmol), D-2(22.21g,70mmol) and sodium tert-butoxide (12.11g,126mmol) were dissolved in 250ml of degassed toluene under argon, palladium acetate (0.55g,2.45mmol) and triphenylphosphine (0.64g,2.45mmol) were added with stirring, and the mixture of the above reactants was heated under reflux for 7 h. After the reaction is finished, cooling to room temperature, cooling the reaction mixture to room temperature, adding 70ml of deionized water for washing, stirring, repeating the operation for three times, concentrating the organic layer under reduced pressure to one third of the volume of the system, stirring for crystallization, filtering, leaching with toluene, recrystallizing with toluene to obtain an intermediate E-8(27.59g, 83%), and detecting the solid purity by HPLC (high performance liquid chromatography) to be not less than 99.8%. Mass spectrum m/z: 473.0559 (theoretical value: 473.0546).
Intermediate E-8(21.37g,45mmol), C-16(11.04g,45mmol) and sodium tert-butoxide (7.78g,81mmol) were dissolved in 200ml of dehydrated toluene under argon, and Pd (dba) was added with stirring2(0.90g,1.57mmol)，P(t-Bu)3(0.32g,1.57mmol), and the mixed solution of the above reactants was heated under reflux for 8 hours. After the reaction is finished, cooling the reaction mixture to room temperature, adding 65ml of deionized water for washing, stirring, standing, repeating the operation for three times, concentrating the organic layer under reduced pressure to one third of the volume of the system, stirring for crystallization, filtering, leaching with toluene, and purifying by silica gel column chromatography with petroleum ether and dichloromethane (1:3) to obtain an intermediate F-1(24.74g, 86%), wherein the solid purity is not less than 99.6% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 657.2495 (theoretical value: 657.2478).
Intermediate F-1(22.37g,35mmol), C-17(10.82g,35mmol) and sodium tert-butoxide (6.05g,63mmol) were dissolved in 250ml of dehydrated toluene under argon, and Pd was added thereto with stirring2(dba)3(1.13g,1.23mmol), X-Phos (0.59g,1.23mmol), and the mixed solution of the above reactants was heated under reflux for 8 h. After the reaction is finished, cooling the mixture to room temperature, adding 80ml of deionized water, stirring, washing, standing, separating liquid, repeating the operation for three times, concentrating the organic layer under reduced pressure to one third of the volume of the system, stirring, crystallizing, filtering, leaching with toluene, recrystallizing and purifying the crude product with toluene to obtain the compounds 1-265(26.82g, 84%), and the purity of the solid is not less than 99.6% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 911.3821 (theoretical value: 911.3876). Theoretical element content (%) C67H49N3O: c, 88.22; h, 5.41; and N, 4.61. Measured elemental content (%): c, 88.18; h, 5.45; n, 4.62.
Synthetic example 7: preparation of Compounds 1-268
By replacing C-2 in Synthesis example 1 with an equimolar amount of C-6 and replacing C-1 with an equimolar amount of C-5, and by following the same procedure, Compound 1-268(37.15g, 81%) was obtained, which had a solid purity of 99.7% or more by HPLC. Mass spectrum m/z: 916.4923 (theoretical value: 916.4974). Theoretical element content (%) C66H36D15N3O: c, 86.42; h, 7.25; n, 4.58. Measured elemental content (%): c, 86.45; h, 7.28; n, 4.53.
Synthesis example 8: preparation of Compounds 1-281
By replacing C-2 in Synthesis example 1 with an equimolar amount of C-10 and replacing C-1 with an equimolar amount of C-9, and by following the same procedure, Compounds 1-281(54.15g, 83%) were obtained, and the purity of the solid was 99.4% or more by HPLC. Mass spectrum m/z: 1304.7312 (theoretical value: 1304.7352). Theoretical element content (%) C96H93N3O: c, 88.37; h, 7.18; and N, 3.22. Measured elemental content (%): c, 88.32; h, 7.22; and N, 3.20.
Synthetic example 9: preparation of Compounds 1-308
By replacing C-1 in Synthesis example 1 with equimolar C-13 and carrying out the same procedures, Compound 1-308(42.14g, 80%) was obtained with a solid purity ≧ 99.7% by HPLC. Mass spectrum m/z: 1053.4671 (theoretical value: 1053.4658). Theoretical element content (%) C78H59N3O: c, 88.86; h, 5.64; and N, 3.99. Measured elemental content (%): c, 88.87; h, 5.67; and N, 3.94.
Synthetic example 10: preparation of Compounds 1-313
Synthesis example 1 was repeated in the same manner except for replacing C-1 with equimolar C-14 to give compound 1-313(41.09g, 82%) having a solid purity of 99.5% by HPLC. Mass spectrum m/z: 1001.4321 (theoretical value: 1001.4345). Theoretical element content (%) C74H55N3O: c, 88.68; h, 5.53; n, 4.19. Measured elemental content (%): c, 88.65; h, 5.58; and N, 4.15.
Synthetic example 11: preparation of Compounds 1-322
Compound 1-322(45.44g, 79%) was obtained by replacing C-1 in Synthesis example 1 with equimolar C-18 and carrying out the same procedure, and the purity of the solid was ≧ 99.5% by HPLC. Mass spectrum m/z: 1149.4672 (theoretical value: 1149.4658). Theoretical element content (%) C86H59N3O: c, 89.79; h, 5.17; and N, 3.65. Measured elemental content (%): c, 89.74; h, 5.12; and N, 3.61.
Synthetic example 12: synthesis of Compound 1
Synthesis of intermediate A-1
600mL of tetrahydrofuran solvent, the raw material a-1(16.39g, 60mmol), the raw material b-1(13.95g, 60mmol), and pd (dppf) Cl were added to a three-necked flask in this order under nitrogen protection2(0.44g, 0.6mmol) and potassium acetate (7.07g, 72mmol), the mixture was stirred and the reaction was heated under reflux at 80 ℃ for 5 hours under nitrogen. After the reaction had ended, the mixture was cooled and 80mL of distilled water were added, filtered through Celite, the filtrate was concentrated, recrystallized from toluene, filtered off with suction and rinsed with toluene to give a recrystallized solid, c-1 (C-1)18.05g, yield 79%). Mass spectrum m/z: 380.1345 (theoretical value: 380.1332).
400mL of tetrahydrofuran solvent, c-1(15.24g, 40mmol), the starting material d-1(10.16g, 40mmol), pd (dppf) Cl were added to a three-necked flask in this order under nitrogen protection2(0.29g, 0.4mmol) and cesium carbonate (16.94g, 52mmol), stirring the mixture, and heating at 100 ℃ under nitrogen for reflux for 7 hours; after the reaction had ceased, the mixture was cooled and 60mL of distilled water was added, filtered over celite, the filtrate was concentrated, recrystallized from toluene, filtered off with suction and rinsed with toluene to give a recrystallized solid, yielding intermediate A-1(14.36g, 76% yield). Mass spectrum m/z: 472.2583 (theoretical value: 472.2574).
Synthesis of Compound 1
To a three-necked flask, 250mL of a 1, 4-dioxane solvent, intermediate A-1(14.17g, 30mmol), starting material e-1(8.03g, 30mmol), and pd were added in this order under a nitrogen blanket2(dba)3(0.27g, 0.3mmol) and 50% tri-tert-butylphosphine (0.2mL, 0.4mmol), potassium carbonate (4.55g, 33mmol), stirring the mixture, refluxing under nitrogen for 10 hours, after completion of the reaction, cooling naturally, filtering, washing the cake with 60mL of deionized water, repeating the operation three times with cyclohexane: separating, purifying and refining ethyl acetate 10:1 by column chromatography as eluent to obtain compound 1(12.48g, yield 72%) with HPLC purity not less than 99.2%.
Mass spectrum m/z: 577.2523 (theoretical value: 577.2518). Theoretical element content (%) C42H31N3: c, 87.32; h, 5.41; and N, 7.27. Measured elemental content (%): c, 87.40; h, 5.35; and N, 7.32.
Synthetic example 13: synthesis of Compound 9
Synthesis of intermediate e-9
Under the protection of nitrogen, a toluene (250 ml)/ethanol (50 ml)/water (50ml) mixed solvent, f-9(18.97g, 60mmol), i-9(7.62g, 60mmol), Pd (PPh) are added into a three-neck flask in sequence3)4(0.68g, 0.59mmol) and potassium carbonate (11.06g, 80mmol), the reaction was stirred at reflux for 9 hours. After the reaction was complete, it was cooled, 60ml of deionized water was added, stirred, washed, and the organic layer was concentrated under reduced pressure, rinsed with toluene, and purified by recrystallization from toluene to give e-9(16.76g, 77% yield). Mass spectrum m/z: 362.0971 (theoretical value: 362.0983).
Synthesis example 12 the same preparation as in Synthesis example 12 was carried out except that e-9 was replaced with e-1 in equimolar amount to give compound 9(14.53g, yield 72%) having a solid purity of 99.4% by HPLC. Mass spectrum m/z: 672.2945 (theoretical value: 672.2937). Theoretical element content (%) C48H28D5N3O: c, 85.69; h, 5.69; and N, 6.25. Measured elemental content (%): c, 85.77; h, 5.73; n, 6.33.
Synthesis example 14: synthesis of Compound 66
Synthesis example 12 was repeated in the same manner as in Synthesis example 12 except that equimolar amounts of a-1 was replaced with a-66, c-1 was replaced with c-66 and A-1 was replaced with A-66 to give compound 66(14.71g, yield 75%) having a solid purity of 99.3% or more by HPLC. Mass spectrum m/z: 653.2826 (theoretical value: 653.2831). Theoretical element content (%) C48H35N3: c, 88.18; h, 5.40; n, 6.43. Measured elemental content (%): c, 88.27; h, 5.23; and N, 6.50.
Synthetic example 15: synthesis of Compound 81
Synthesis example 12 was repeated in the same manner as in Synthesis example 12 except that equimolar amounts of b-1 was replaced with b-81, c-1 was replaced with c-81, and A-1 was replaced with A-81 to give 81(12.74g, yield 77%) as a compound having a purity of 99.7% by HPLC. Mass spectrum m/z: 551.2352 (theoretical value: 551.2361). Theoretical element content(％)C40H29N3: c, 87.08; h, 5.30; and N, 7.62. Measured elemental content (%): c, 87.17; h, 5.22; and N, 7.58.
Synthetic example 16: synthesis of Compound 126
Synthesis example 12 was repeated in the same manner as in Synthesis example 12 except that equimolar amounts of b-1 was replaced with b-126, c-1 was replaced with c-126, and A-1 was replaced with A-126, to give compound 126(13.16g, yield 71%) having a solid purity of 99.5% or more by HPLC. Mass spectrum m/z: 617.2824 (theoretical value: 617.2831). Theoretical element content (%) C45H35N3: c, 87.49; h, 5.71; and N, 6.80. Measured elemental content (%): c, 87.57; h, 5.63; and N, 6.72.
Synthetic example 17: synthesis of Compound 133
Synthesis example 12 was repeated in the same manner as in Synthesis example 12 except that equimolar amounts of b-1 was replaced with b-133, c-1 was replaced with c-133, and A-1 was replaced with A-133 to give compound 133(11.07g, 73% yield), which was not less than 99.2% pure by HPLC. Mass spectrum m/z: 505.2447 (theoretical value: 505.2456). Theoretical element content (%) C36H23D4N3: c, 85.51; h, 6.18; n, 8.31. Measured elemental content (%): c, 85.45; h, 6.23; and N, 8.25.
Synthetic example 18: synthesis of Compound 157
Synthesis example 12 equimolar of a-1 was replaced with a-157, c-1 was replaced with c-157, and A-1 was replaced with A-157 in accordance with the same phase as in Synthesis example 12By the same method, 157(13.56g, 72% yield) of the compound was obtained, and the purity of the solid was ≧ 99.7% by HPLC. Mass spectrum m/z: 627.2667 (theoretical value: 627.2674). Theoretical element content (%) C46H33N3: c, 88.01; h, 5.30; and N, 6.69. Measured elemental content (%): c, 88.09; h, 5.26; and N, 6.72.
Synthetic example 19: synthesis of Compound 169
Synthesis example 12 was repeated in the same manner as in Synthesis example 12 except that equimolar amounts of a-1 was replaced with a-169, b-1 was replaced with b-169, c-1 was replaced with c-169 and A-1 was replaced with A-169 to give 169(12.98g, yield 75%) having a purity of 99.3% by HPLC. Mass spectrum m/z: 576.2557 (theoretical value: 576.2565). Theoretical element content (%) C43H32N2: c, 89.55; h, 5.59; and N, 4.86. Measured elemental content (%): c, 89.61; h, 5.45; and N, 4.91.
Synthesis example 20: synthesis of Compound 192
Synthesis example 12 the same preparation as in Synthesis example 12 was carried out except that e-192 was used instead of equimolar e-1, to give 192(12.82g, 74% yield) as a compound having a purity of 99.5% or more by HPLC. Mass spectrum m/z: 577.2524 (theoretical value: 577.2518). Theoretical element content (%) C42H31N3: c, 87.32; h, 5.41; and N, 7.27. Measured elemental content (%): c, 87.26; h, 5.38; and N, 7.32.
Synthetic example 21: synthesis of Compound 215
Synthesis example 12 was repeated in the same manner as in Synthesis example 12 except that equimolar of a-1 was replaced with a-215, b-1 was replaced with b-215, c-1 was replaced with c-215, A-1 was replaced with A-215, and e-1 was replaced with e-215 to give compound 215(17.69g, yield 77%) having a purity of 99.6% by HPLC. Mass spectrum m/z: 765.2774 (theoretical value: 765.2780). Theoretical element content (%) C56H35N3O: c, 87.82; h, 4.61; and N, 5.49. Measured elemental content (%): c, 87.77; h, 4.57; n, 5.54.
Synthetic example 22: synthesis of Compound 261
Synthesis example 12 was repeated in the same manner as in Synthesis example 12 except that equimolar of a-1 was replaced with a-261, b-1 was replaced with b-261, c-1 was replaced with c-261, and A-1 was replaced with A-261 to give 261(15.85g, 73% yield) as a compound having a purity of 99.4% by HPLC. Mass spectrum m/z: 723.2668 (theoretical value: 723.2674). Theoretical element content (%) C54H33N3: c, 89.60; h, 4.60; and N, 5.80. Measured elemental content (%): c, 89.55; h, 4.57; and N, 5.76.
Synthetic example 23: preparation of Compound 3-1
Step 1: synthesis of intermediate N-1
To a reaction flask were added compound M-1(13.65g,62.23mmol), L-1(12.47g,60.21mmol), sodium tert-butoxide (8.61g,89.56mmol), palladium acetate (0.27g,1.20mmol), triphenylphosphine (0.31g,1.20mmol) and 250ml toluene in this order, and the mixture was reacted under heating at 90 ℃ for 4.5 hours under argon. After the reaction is finished, the reaction mixture is cooled to room temperature, washed by deionized water, dried by anhydrous magnesium sulfate, concentrated to a small amount, and purified by silica gel column chromatography by using normal hexane as a mobile phase to obtain an intermediate N-1(17.89g, yield 86%), and the purity of solid is not less than 99.5% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 359.1567 (theoretical value: 359.1554).
Step 2: synthesis of Compound 3-1
To a reaction flask were added the intermediates N-1(15.62g,45.21 mmol), X-1(12.81g,43.12mmol), sodium tert-butoxide (6.22g,64.68mmol), Pd in that order2(dba)3(0.79g,0.86mmol), X-Phos (0.41g,0.86mmol) and 200mL of toluene under the protection of argon, heating and refluxing the mixed solution of the reactants for 4 hours, after the reaction is finished, pouring the reaction solution into 500mL of water, adding 400mL of dichloromethane, carrying out layer separation, extracting the water layer for 3 times by using 200mL of dichloromethane, combining organic phases, recovering the solvent under reduced pressure, and recrystallizing the toluene to obtain the compound 3-1(20.34g, yield of 84%), wherein the purity of the solid is not less than 99.3% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 561.2074 (theoretical value: 561.2093). Theoretical element content (%) C42H27NO: c, 89.81; h, 4.85; and N, 2.49. Measured elemental content (%): c, 89.76; h, 4.87; and N, 2.52.
Synthetic example 24: preparation of Compound 3-2
The same procedures used in Synthesis example 23 were repeated except for replacing M-1 and L-1 in Synthesis example 23 with equimolar amounts of M-2 and L-2 to give 3-2(20.59g, yield 85%) having a purity of 99.7% by HPLC. Mass spectrum m/z: 561.2019 (theoretical value: 561.2093). Theoretical element content (%) C42H27NO: c, 89.81; h, 4.85; and N, 2.49. Measured elemental content (%): c, 89.85; h, 4.87; n, 2.44.
Synthetic example 25: preparation of Compounds 3-9
The same procedures used in Synthesis example 23 were repeated except for replacing L-1 in Synthesis example 23 with equimolar amount of L-3 to give compound 3-9(22.83g, yield 83%)) And the purity of the solid is not less than 99.8 percent through HPLC detection. Mass spectrum m/z: 637.2425 (theoretical value: 637.2406). Theoretical element content (%) C48H31NO: c, 90.40; h, 4.90; and N, 2.20. Measured elemental content (%): c, 90.43; h, 4.86; and N, 2.23.
Synthetic example 26: preparation of Compounds 3-38
By substituting M-1, L-1 and X-1 in Synthesis example 23 with equimolar amounts of M-2, L-4 and X-2, the same preparation process as in Synthesis example 23 was carried out to give compound 3-38(22.55g, yield 82%) having a purity of 99.4% by HPLC. Mass spectrum m/z: 637.2425 (theoretical value: 637.2406). Theoretical element content (%) C48H31NO: c, 90.40; h, 4.90; and N, 2.20. Measured elemental content (%): c, 90.35; h, 4.92; and N, 2.24.
Synthetic example 27: preparation of Compounds 3-77
By replacing X-1 in Synthesis example 23 with an equimolar amount of X-3 and following the same preparation method as in Synthesis example 23, Compound 3-77(19.38g, yield 80%) was obtained with a solid purity of 99.6% or more by HPLC. Mass spectrum m/z: 561.2071 (theoretical value: 561.2093). Theoretical element content (%) C42H27NO: c, 89.81; h, 4.85; and N, 2.49. Measured elemental content (%): c, 89.83; h, 4.88; n, 2.44.
Synthetic example 28: preparation of Compounds 3-107
Compound 3-107(21.73g, obtained by substituting M-1 and X-1 in Synthesis example 23 with equimolar amounts of M-3 and X-4, and carrying out the same preparation process as in Synthesis example 23The rate is 79%), and the purity of the solid is not less than 99.5% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 637.2443 (theoretical value: 637.2406). Theoretical element content (%) C48H31NO: c, 90.40; h, 4.90; and N, 2.20. Measured elemental content (%): c, 90.43; h, 4.86; and N, 2.22.
Synthetic example 29: preparation of Compounds 3-117
By substituting L-1 and X-1 in Synthesis example 23 with equimolar amounts of L-3 and X-5, the same preparation process as in Synthesis example 23 was repeated to give 3-117(23.38g, yield 85%) having a purity of 99.3% by HPLC. Mass spectrum m/z: 637.2432 (theoretical value: 637.2406). Theoretical element content (%) C48H31NO: c, 90.40; h, 4.90; and N, 2.20. Measured elemental content (%): c, 90.45; h, 4.88; and N, 2.16.
Synthetic example 30: preparation of Compounds 3-134
By the same method as in Synthesis example 23 except for replacing M-1, L-1 and X-1 in Synthesis example 23 with equimolar amounts of M-2, L-4 and X-6, 3-134(23.10g, yield 84%) was obtained with a solid purity of 99.7% by HPLC. Mass spectrum m/z: 637.2423 (theoretical value: 637.2406). Theoretical element content (%) C48H31NO: c, 90.40; h, 4.90; and N, 2.20. Measured elemental content (%): c, 90.38; h, 4.85; and N, 2.25.
Synthetic example 31: preparation of Compounds 3-194
Synthesis example 23 was repeated in the same manner as in Synthesis example 23 except that M-1, L-1 and X-1 were replaced with equimolar amounts of M-2, L-2 and X-7To obtain the compound 3-194(21.42g, yield 86%), and the solid purity is not less than 99.8% by HPLC. Mass spectrum m/z: 577.1823 (theoretical value: 577.1864). Theoretical element content (%) C42H27And NS: c, 87.32; h, 4.71; and N, 2.42. Measured elemental content (%): c, 87.30; h, 4.75; and N, 2.38.
Synthetic example 32: preparation of Compounds 3-237
By replacing M-1 and L-1 in Synthesis example 23 with equimolar amounts of M-2 and L-5 and following the same preparation method as in Synthesis example 23, Compound 3-237(21.89g, yield 83%) was obtained with a solid purity ≧ 99.5% by HPLC. Mass spectrum m/z: 611.2221 (theoretical value: 611.2249). Theoretical element content (%) C46H29NO: c, 90.32; h, 4.78; and N, 2.29. Measured elemental content (%): c, 90.36; h, 4.75; and N, 2.25.
Synthetic example 33: preparation of Compounds 3-240
By replacing M-1 and L-1 in Synthesis example 23 with equimolar amounts of M-2 and L-6 and following the same preparation method as in Synthesis example 23, 3-240(23.11g, yield 81%) was obtained with a solid purity ≧ 99.4% by HPLC. Mass spectrum m/z: 661.2445 (theoretical value: 661.2406). Theoretical element content (%) C50H31NO: c, 90.74; h, 4.72; and N, 2.12. Measured elemental content (%): c, 90.72; h, 4.69; and N, 2.16.
Comparative example 1 device preparation example:
comparative example 1: the organic electroluminescent device is prepared by a vacuum thermal evaporation method. The experimental steps are as follows: repeatedly washing the ITO glass substrate with a glass cleaning agent, then washing the ITO glass substrate in distilled water for 2 times, ultrasonically washing for 15 minutes, after the washing with the distilled water is finished, ultrasonically washing solvents such as isopropanol, acetone, methanol and the like in sequence, drying at 120 ℃, and conveying to an evaporation plating machine.
Evaporating a hole injection layer compound H1 on the prepared ITO-Ag-ITO glass substrate in a layer-by-layer vacuum evaporation mode: p1 (3%: 97%: mixed)/40 nm, a hole transport layer compound (1-1/52 nm), a luminescent layer (main body RH-3: RH-10: RD-10 (45%: 45%: 10%: mixed))/30 nm, an electron transport layer compound (ET-1/29 nm), an electron injection layer (LiF/1 nm), a cathode Mg-Ag (Mg: Ag doping ratio 9:1)/19nm, and a capping layer compound (3-1/61 nm).
Comparative example 2: a comparative organic electroluminescent element 2 was obtained by replacing the hole transport layer compound 1-1 with the compound HT-1 and the electron transport layer compound ET-1 with the compound 1 in comparative example 1, and the other steps were the same. Comparative example 3: a comparative organic electroluminescent device 3 was obtained by replacing the hole transport layer compound 1-1 of comparative example 1 with the compound HT-1, the other being the same.
Comparative example 4: a comparative organic electroluminescent device 4 was obtained by replacing the hole transport layer compound 1-1 with the compound 1-49 and the capping layer compound 3-1 with the compound 3-9 in comparative example 1, and the other was the same. Comparative example 5: comparative organic electroluminescent element 5 was obtained by replacing hole transport layer compound 1-1 with compound HT-1, electron transport layer compound 1 with compound 66, and capping layer compound 3-1 with compound 3-9 in comparative example 1, the other being the same. Comparative example 6: a comparative organic electroluminescent device 6 was obtained by replacing the hole transport layer compound 1-1 with the compound HT-1 and the capping layer compound 3-1 with the compound 3-9 in comparative example 1, and the other steps were the same.
Comparative example 7: comparative organic electroluminescent element 7 was obtained by replacing hole transport layer compound 1-1 with compound 1-281 and capping layer compound 3-1 with compound 3-134 in comparative example 1, and the other steps were the same. Comparative example 8: a comparative organic electroluminescent element 8 was obtained by replacing the hole transport layer compound 1-1 with the compound HT-1, the electron transport layer compound 1 with the compound 169, and the capping layer compound 3-1 with the compound 3-134 in comparative example 1, which were otherwise the same. Comparative example 9: a comparative organic electroluminescent device 9 was obtained by replacing the hole transport layer compound 1-1 with the compound HT-1 and the capping layer compound 3-1 with the compound 3-134 in comparative example 1, and the other steps were the same.
[ application examples 1 to 11]
Application example 1: the electron transport layer compound ET-1 in comparative example 1 of the organic electroluminescent device was replaced with the compound 1 of the present invention, and the same was repeated except that the organic electroluminescent device 1 was used.
Compounds 1 to 1 in application example 1 were substituted with compounds 1 to 15, compounds 1 to 49, compounds 1 to 95, compounds 1 to 216, compounds 1 to 265, compounds 1 to 268, compounds 1 to 281, compounds 1 to 308, compounds 1 to 313, and compounds 1 to 322 of the present invention, respectively, in this order;
compound 9, compound 66, compound 81, compound 126, compound 133, compound 157, compound 169, compound 192, compound 215, and compound 261, respectively, of the present invention were used in this order instead of compound ET-1 in application example 1;
and organic electroluminescent element application example 2 through application example 11 were prepared in the same manner as in comparative example 1, except that compound 3-1 in application example 1 was replaced with compound 3-2, compound 3-9, compound 3-38, compound 3-77, compound 3-107, compound 3-117, compound 3-134, compound 3-194, compound 3-237, and compound 3-240 according to the present invention, respectively.
A joint IVL test system is formed by test software, a computer, a K2400 digital source meter manufactured by Keithley of the United states and a PR788 spectral scanning luminance meter manufactured by Photo Research of the United states to test the driving voltage and the luminous efficiency of the organic electroluminescent device. The environment of the test is atmospheric environment, and the temperature is room temperature.
The results of the light emission characteristic test of the obtained organic electroluminescent device are shown in table 1. Table 1 shows the results of the test of the light emitting characteristics of the light emitting devices prepared from the compounds prepared in the synthesis examples of the present invention and the comparative materials.
Table 1 test of light emitting characteristics of light emitting device
As can be seen from the results in table 1, the organic electroluminescent device of the present invention has advantages of high luminous efficiency and low driving voltage as compared with comparative examples 1 to 9, and is an organic electroluminescent device having good performance. The combination of the specific hole transport layer material and the specific electron transport layer material reflects the synergistic effect of the hole transport layer and the electron transport layer, and the covering layer material is added, so that the organic electroluminescent device is prepared.
It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.
Claims (10)
1. An organic electroluminescent device comprises a substrate, an anode, an organic layer and a cathode, and is characterized in that the organic layer comprises a hole transport layer and an electron transport layer, the hole transport layer contains a triamine compound represented by a formula I, the electron transport layer contains a heterocyclic compound represented by a formula II,
wherein, in formula I, X is selected from O or S;
the A ring, the B ring or the C ring is independently selected from a benzene ring, a naphthalene ring or no;
the R groups are the same or different from each other and are independently selected from one of methyl, ethyl, phenyl, tolyl, pentadeuterophenyl and naphthyl, or two adjacent R groups can be bonded to form a cyclic structure;
ar is1、Ar2、Ar3、Ar4Independently selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
said L1、L2、L3、L4、L5、L6Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;
the R is1、R2Independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
in the formula II, R is0The two R are same or different from each other and are independently selected from one of methyl, ethyl, phenyl, tolyl, pentadeuterated phenyl and naphthyl, or two adjacent R0The group can be bonded with the connected segment to form a spirofluorene cyclic structure;
said X1To X5Are the same or different from each other and are each independently N or C (R)w) And at least one is N, when C (R)w) When there are plural, plural C (R)w) Are identical to or different from each other, wherein RwOne selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
Rx、Ry、Rzthe same or different from each other, and are respectively and independently selected from hydrogen, deuterium, halogen group, cyano, nitro, amino, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15One of unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or two adjacent groups can be bonded to form a cyclic structure; x is 0, 1,2, 3 or 4; y is 0, 1,2, 3 or 4; z is 0, 1,2, 3 or 4;
l is selected from one of single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30;
n is 0, 1,2 or 3.
2. The organic electroluminescent device according to claim 1, wherein the Ar is Ar1、Ar2、Ar3、Ar4Independently selected from one of the following substituents:
the R is11One selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, adamantyl, norbornyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl and pyrenyl;
h is 0, 1,2, 3 or 4; i is 0, 1,2, 3, 4 or 5; j is 0, 1,2, 3, 4, 5, 6 or 7; k is 0, 1,2, 3, 4, 5, 6, 7, 8 or 9.
3. The organic electroluminescent device of claim 1, wherein Ar is Ar1、Ar2One selected from the following substituents:
4. the organic electroluminescent device according to claim 1, wherein the Ar is Ar3、Ar4One selected from the following substituents:
5. the organic electroluminescent device according to claim 1, wherein the organic electroluminescent device is characterized in that
Is selected from one of the groups shown below,
z is1Is 0, 1,2 or 3; z is a radical of2Is 0, 1 or 2.
6. The organic electroluminescent device according to claim 1, wherein R isx、Ry、RzIdentical to or different from each other, each independently selected from hydrogen, deuterium, a halogen group, cyano, nitro, amino, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl or from one of the structures shown below,
7. the organic electroluminescent device according to claim 1, wherein L is selected from the group consisting of a single bond, a substituted or unsubstituted cyclohexylene group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted benzofluorenylene group, a substituted or unsubstituted dibenzofluorenylene group, a substituted or unsubstituted spirobifluorenylene group, a substituted or unsubstituted benzospirobifluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted quinolinylene group, Substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinylene, substituted or unsubstituted phenanthroline, substituted or unsubstituted azaanthracene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, or substituted or unsubstituted carbazolyl.
8. The organic electroluminescent device according to claim 1, further comprising a capping layer containing a triarylamine compound represented by formula III,
in formula III, the XaSelected from O or S;
ar isa、ArbIndependently selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl, with the proviso that AraOr ArbAt least one of them is a condensed ring group;
said La、Lb、LcIndependently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;
the R isa、RbIndependently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted CUnsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl.
9. The organic electroluminescent device according to claim 8, wherein the Ar isaSelected from substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted naphthyl
One of a substituted or unsubstituted perylene group.
10. The organic electroluminescent device according to claim 8, wherein the Ar isbOne selected from the following substituents:
wherein Ad is adamantyl or norbornyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110990159.2A CN113594395B (en) | 2021-08-26 | 2021-08-26 | Organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110990159.2A CN113594395B (en) | 2021-08-26 | 2021-08-26 | Organic electroluminescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113594395A true CN113594395A (en) | 2021-11-02 |
| CN113594395B CN113594395B (en) | 2024-04-12 |
Family
ID=78239822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110990159.2A Active CN113594395B (en) | 2021-08-26 | 2021-08-26 | Organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113594395B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170271610A1 (en) * | 2016-03-18 | 2017-09-21 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, display device, electronic device, and lighting device |
| CN110416422A (en) * | 2018-04-28 | 2019-11-05 | 江苏三月光电科技有限公司 | Organic electroluminescence device and display including it |
| CN111933818A (en) * | 2020-08-12 | 2020-11-13 | 长春海谱润斯科技有限公司 | Organic light-emitting device |
| KR20200129993A (en) * | 2019-05-10 | 2020-11-18 | 주식회사 엘지화학 | Organic light emitting device |
| CN113196515A (en) * | 2019-07-31 | 2021-07-30 | 株式会社Lg化学 | Organic light emitting device |
-
2021
- 2021-08-26 CN CN202110990159.2A patent/CN113594395B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170271610A1 (en) * | 2016-03-18 | 2017-09-21 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, display device, electronic device, and lighting device |
| CN110416422A (en) * | 2018-04-28 | 2019-11-05 | 江苏三月光电科技有限公司 | Organic electroluminescence device and display including it |
| KR20200129993A (en) * | 2019-05-10 | 2020-11-18 | 주식회사 엘지화학 | Organic light emitting device |
| CN113196515A (en) * | 2019-07-31 | 2021-07-30 | 株式会社Lg化学 | Organic light emitting device |
| CN111933818A (en) * | 2020-08-12 | 2020-11-13 | 长春海谱润斯科技有限公司 | Organic light-emitting device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113594395B (en) | 2024-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112341449B (en) | Triarylamine organic compound containing spirofluorene and organic light-emitting device thereof | |
| CN113620917B (en) | Triarylamine compound and organic light-emitting device thereof | |
| CN113336744B (en) | Heterocyclic derivative and organic electroluminescent device thereof | |
| EP3826080B1 (en) | Nitrogen-containing compound, electronic component and electronic device | |
| CN115057838B (en) | Aromatic amine organic compound and organic light-emitting device thereof | |
| CN113735793B (en) | Compound containing benzo five-membered heterocycle and organic electroluminescent device thereof | |
| CN115417806B (en) | Carbazole compound and organic electroluminescent device thereof | |
| CN113121408A (en) | Nitrogen-containing compound, electronic component, and electronic device | |
| CN113527280B (en) | Heterocyclic compound and organic electroluminescent device thereof | |
| CN114989069A (en) | Nitrogen-containing compound, electronic component, and electronic device | |
| CN113816921A (en) | Heterocyclic compound and organic electroluminescent device thereof | |
| CN113735780A (en) | Benzo five-membered heterocyclic derivative and organic electroluminescent device thereof | |
| CN113336771A (en) | Condensed ring carbazole derivative and organic electroluminescent device thereof | |
| CN115650899B (en) | Nitrogen-containing compound, electronic component and electronic device | |
| CN114621181B (en) | Star-shaped tetramine derivative and organic electroluminescent device thereof | |
| JP2022517639A (en) | Organic electroluminescent compounds and organic electroluminescent devices containing them | |
| CN116444384A (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN116143739A (en) | Diamine compound and organic light-emitting device thereof | |
| CN115745906A (en) | Compound containing heterocycle and organic electroluminescent device thereof | |
| CN111892531B (en) | Organic compound and organic electroluminescent device thereof | |
| CN114530571A (en) | Organic electroluminescent element | |
| CN113717196A (en) | Azabenzoxazole or thiazole compound and organic electroluminescent device thereof | |
| CN113582855A (en) | Diamine organic compound and organic light-emitting device thereof | |
| CN113594395B (en) | Organic electroluminescent device | |
| CN112510160B (en) | Organic light-emitting device |
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 |