CN114315692B - Aromatic amine compound and organic electroluminescent device comprising same - Google Patents
Aromatic amine compound and organic electroluminescent device comprising same Download PDFInfo
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- CN114315692B CN114315692B CN202011627377.1A CN202011627377A CN114315692B CN 114315692 B CN114315692 B CN 114315692B CN 202011627377 A CN202011627377 A CN 202011627377A CN 114315692 B CN114315692 B CN 114315692B
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- organic electroluminescent
- electroluminescent device
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- -1 Aromatic amine compound Chemical class 0.000 title claims abstract description 65
- 239000000463 material Substances 0.000 claims abstract description 121
- 230000005525 hole transport Effects 0.000 claims abstract description 89
- 238000002347 injection Methods 0.000 claims description 72
- 239000007924 injection Substances 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004431 deuterium atom Chemical group 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 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 5
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000006836 terphenylene group Chemical group 0.000 claims description 3
- 239000007769 metal material Substances 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 189
- 239000011799 hole material Substances 0.000 description 74
- 239000011368 organic material Substances 0.000 description 24
- 239000010408 film Substances 0.000 description 21
- 239000000758 substrate Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 15
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 238000007738 vacuum evaporation Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
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- 150000001616 biphenylenes Chemical group 0.000 description 5
- 229920001940 conductive polymer Polymers 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000005264 aryl amine group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
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- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
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- 238000013508 migration Methods 0.000 description 2
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
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- 229910052709 silver Inorganic materials 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
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- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000005558 triazinylene group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
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- OMDTUSYJJFBYMG-UHFFFAOYSA-N 2,4-bis(9,9-dimethylfluoren-2-yl)-6-naphthalen-2-yl-1,3,5-triazine Chemical compound C1=CC=C2C(C)(C)C3=CC(C=4N=C(N=C(N=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 OMDTUSYJJFBYMG-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UVEAFTFQMHUWEY-UHFFFAOYSA-N methane;1,2,4,5-tetrafluoro-3,6-dioxocyclohexane-1,2,4,5-tetracarbonitrile Chemical compound C.C.N#CC1(F)C(=O)C(F)(C#N)C(F)(C#N)C(=O)C1(F)C#N UVEAFTFQMHUWEY-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 229910052759 nickel 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
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000005565 oxadiazolylene group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005550 pyrazinylene group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002210 silicon-based material Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001894 space-charge-limited current method Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an arylamine compound of a general formula (1) as defined in the specification and application thereof as a hole transport material in an organic electroluminescent device. The invention also relates to an organic electroluminescent device which sequentially comprises an anode, a hole transport region, a light emitting region, an electron transport region and a cathode from bottom to top, wherein the hole transport region comprises an arylamine compound of the general formula (1) as described in the specification, and a display device comprising the organic electroluminescent device.
Description
Technical Field
The present invention relates to the field of semiconductor technology, and more particularly, to a novel aromatic amine compound, its use as a hole transport material in an organic electroluminescent device, an organic electroluminescent device including the aromatic amine compound, and a display apparatus including the organic electroluminescent device.
Background
Carriers (holes and electrons) in an organic electroluminescent device (OLED) are respectively injected into the device by two electrodes of the device under the drive of an electric field, and meet and recombine and emit light in an organic light-emitting layer. High-performance organic electroluminescent devices require various organic functional materials to have good photoelectric properties. For example, a charge transport material is required to have good carrier mobility. The injection and transmission characteristics of the hole injection layer material and the hole transmission layer material used in the existing organic electroluminescent device are relatively weak, and the hole injection and transmission rates are not matched with the electron injection and transmission rates, so that the composite area is greatly deviated, and the stability of the device is not facilitated. In addition, reasonable energy level matching of the hole injection layer material and the hole transport layer material is an important factor for improving the efficiency and the service life of the device, so how to adjust the balance degree of holes and electrons and adjust the recombination region is always an important subject in the field.
Blue organic electroluminescent devices are always soft ribs in full-color OLED development, so that the efficiency, service life and other performances of blue light devices are not fully improved until now, and therefore, how to improve the performances of the devices is still a critical problem and challenge in the field. Since the blue light host materials currently used in the market are mostly electron-biased host materials, the hole transport materials are required to have excellent hole transport properties in order to adjust the carrier balance of the light emitting layer. The better the hole injection and transmission, the more the adjusting composite area is deviated to the side far away from the electron blocking layer, so that the light is emitted far away from the interface, the performance of the device is improved, and the service life of the device is prolonged. Therefore, the hole transport region material is required to have high hole injection property, high hole mobility, high electron blocking property, and high electron weatherability.
The hole transport material has a relatively thick film thickness, and therefore, heat resistance and amorphism of the material have a critical influence on the lifetime of the device. The material with poor heat resistance is easy to decompose in the evaporation process, pollutes the evaporation cavity and damages the service life of the device; the material with poor film phase stability can be crystallized in the use process of the device, and the service life of the device is reduced. Therefore, the hole transport material is required to have high film phase stability and decomposition temperature during use. However, development of a material for a stable and effective organic material layer of an organic electroluminescent device has not been sufficiently achieved. Accordingly, there is a continuous need to develop a new material to better meet the performance requirements of organic electroluminescent devices.
Disclosure of Invention
In order to solve the above problems, the present invention prepares an organic electroluminescent device by combining materials excellent in hole and electron injection/transport properties, film stability and weather resistance, which is helpful to improve the recombination efficiency of electrons and holes, to improve the exciton utilization rate, and the obtained device has high efficiency and long lifetime.
Accordingly, the present inventors have developed a novel arylamine compound in which an arylamine group is used as a basic skeleton, and a nitrogen atom of the arylamine group and an optionally substituted carbazole group are respectively linked to benzene rings adjacent to each other through linking groups. The connection mode enables the compound to have excellent hole migration capability, film phase stability and weather resistance. Further, the present inventors have found that when such an arylamine compound is used as a hole transport material to form an organic electroluminescent device, the device can exhibit effects such as improvement in device efficiency and prolongation of lifetime.
It is therefore an object of the present invention to provide a novel arylamine compound having the following general formula (1):
wherein the method comprises the steps of
R、R 1 、R 0 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted 5-30 membered heteroaryl group having at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom, wherein R, R 1 、R 0 And only two of them are represented by hydrogen atoms and deuterium atoms;
R 5 represented by phenyl, naphthyl or biphenyl;
R 4 represented by hydrogen atom, deuterium atom, aryl group having 6-30 ring-forming carbon atoms, 5-30 membered heteroaryl group having at least one hetero atom selected from oxygen atom, sulfur atom or nitrogen atom, wherein R 4 The connection mode with the general formula (1) comprises two modes of ring combination and substitution;
R 2 、R 3 each independently represented by the structure shown below;
L 1 、L 2 each independently represents a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group;
R 6 、R 7 each independently is represented by a hydrogen atom, a deuterium atom, an aryl group having 6 to 30 ring-forming carbon atoms, a 5-to 30-membered heteroaryl group having at least one hetero atom selected from an oxygen atom, a sulfur atom or a nitrogen atom, wherein R 6 、R 7 The connection mode of (a) is two modes of parallel ring and substitution;
wherein the substituents are selected from deuterium atoms, phenyl groups, naphthyl groups or biphenyl groups.
It is another object of the present invention to provide the use of the arylamine compounds of formula (1) as hole transport materials in organic electroluminescent devices. In another embodiment, the present invention provides the use of an arylamine compound of formula (1) as a hole transport material in a blue organic electroluminescent device.
Another object of the present invention is to provide an organic electroluminescent device having improved luminous efficiency and lifetime, which comprises an anode, a hole transporting region, a light emitting region, an electron transporting region, and a cathode in this order from bottom to top, wherein the hole transporting region comprises the arylamine compound of formula (1) according to the present invention.
It is also an object of the present invention to provide a full-color display device comprising three pixels of red, green and blue, the full-color display device comprising the organic electroluminescent device of the present invention. In another embodiment, the present invention also provides a blue display device comprising the arylamine compound of general formula (1) of the present invention as a hole transport material. In another embodiment, the present invention also provides a full color display apparatus including red, green, and blue three pixels including a red organic electroluminescent device, a blue organic electroluminescent device, and a green organic electroluminescent device, the devices of the red, green, and blue three pixels having a common hole injection layer and a first hole transport layer. In another embodiment, the present invention also provides a full color display device including red, green, and blue three pixels, wherein the devices of the red, green, and blue three pixels have a common hole injection layer and a first hole transport layer, and the second hole transport layer of the devices of the blue pixels is a common layer.
Advantageous effects
The arylamine compound of the present invention, wherein an arylamine group is used as a basic skeleton, and a nitrogen atom of the arylamine group and an optionally substituted carbazole group are respectively connected to benzene rings adjacent to each other through a linking group. The connection mode ensures that the compound has lower structure recombination energy which needs to be overcome in the hole transmission process due to the tertiary amine structure, and is favorable for hole transmission, so that the compound has excellent hole migration capability, and the hole can be effectively transmitted to the light-emitting layer, thereby prolonging the service life of the device.
The compound disclosed by the invention has the advantages that due to the existence of carbazole groups, a stable electron transfer state (CT state) is easier to form with a P-type doped material, so that a good ohmic contact is formed between the hole injection layer and an anode interface, space charge limiting current is facilitated to be formed, carrier injection is promoted, the exciton concentration of a luminescent layer is improved, and further the device efficiency is improved.
Compared with the hole transport material commonly used in the industry at present, the compound provided by the invention has a relatively deep HOMO energy level, so that the injection barrier between the hole transport material and the main body material of the light-emitting region is reduced, a space charge limited current region can be achieved under a lower driving voltage, and the device efficiency is effectively improved.
In addition, the arylamine compound has excellent film phase stability and high weather resistance, so that the interface stability is relatively good, cracking cannot occur due to high electron concentration, and the arylamine compound also has excellent high-temperature weather resistance, so that the aging of a device cannot occur due to heat generated in the device lighting process.
In addition, the arylamine compound is combined with the nitrogen heterocycle electron transport material, so that electrons and holes are in an optimal balance state, and the arylamine compound has higher efficiency and also has better service life, in particular to the high-temperature service life of a device.
Drawings
Fig. 1 schematically illustrates a cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
1 represents an anode; 10 denotes a hole transport region, 2 denotes a hole injection layer, 3 denotes a first hole transport layer, and 4 denotes a second hole transport layer; 5 represents a light emitting region; 20 denotes an electron transport region, 6 denotes an electron transport layer, and 7 denotes an electron injection layer; 8 is denoted as cathode; 9 denotes a cover layer; 30 denotes an organic light emitting diode.
FIG. 2 is a nuclear magnetic spectrum of compound H1.
FIG. 3 nuclear magnetic resonance spectrum of compound H21.
FIG. 4 nuclear magnetic resonance spectrum of compound H182.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are merely illustrative, the invention is not limited thereto and the invention is defined by the scope of the claims.
In the present invention, unless otherwise indicated, all operations are carried out at room temperature under normal pressure.
In the present invention, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule unless otherwise specified. Further, reference in the present specification to "difference in HOMO energy levels" and "difference in LUMO energy levels" means a difference in absolute values of each energy value. Furthermore, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between energy levels is also a comparison of the magnitudes of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level, the lower the energy of the energy level.
In the present invention, when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate or intervening layers may also be present. Further, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, words of "upper", "lower", "top" and "bottom", etc., which are used to indicate orientations, indicate only orientations in a certain specific state, and do not mean that the relevant structure can only exist in the orientations; conversely, if the structure can be repositioned, for example inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of an electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is farther from the substrate is the "top" side.
In this specification, the term "substituted" means that one or more hydrogen atoms on a given atom or group is replaced by the given group, provided that the normal valency of the given atom is not exceeded under existing circumstances.
In this specification, the term "aryl" refers to a fully unsaturated monocyclic, polycyclic, or fused polycyclic (i.e., rings which share a pair of adjacent carbon atoms) system having from 6 to 30 ring carbon atoms.
In this specification, the term "heteroaryl" refers to a fully unsaturated 5-30 membered cyclic group having at least one heteroatom selected from N, O and S, including but not limited to single rings, multiple rings, fused rings, or combinations thereof. When the heteroaryl group is a fused ring, each or all of the rings of the heteroaryl group may contain at least one heteroatom.
More specifically, substituted or unsubstituted C 6 -C 30 Aryl and/or substituted or unsubstituted 5-to 30-membered heteroaryl means substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstitutedA substituted or unsubstituted biphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted indenyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridine, a substituted or unsubstituted benzoxazine, a substituted or unsubstituted quinazoline, a substituted or unsubstituted buprofen-rphine, a substituted or unsubstituted buprofen-yl An oxazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a fused ring of a combination of the foregoing, but is not limited thereto.
In the present specification, substituted or unsubstituted C 6 -C 30 Arylene or substituted or unsubstituted 5-30 membered heteroarylene refers to a substituted or unsubstituted C as defined above and having two linking groups, respectively 6 -C 30 Aryl or substituted or unsubstituted 5-30 membered heteroaryl, for example, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted pyrenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted phenyleneA group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted triazolylene group, a substituted or unsubstituted oxazolylene group, a substituted or unsubstituted thiazolylene group, a substituted or unsubstituted oxadiazolylene group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolylene group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted naphthyridine group A substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted rphyrazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a fused ring of a combination of the foregoing groups, but is not limited thereto.
In this specification, the hole feature refers to a feature that can supply electrons when an electric field is applied and is attributed to a conductive feature according to the Highest Occupied Molecular Orbital (HOMO) level, and holes formed in the anode are easily injected into and transported in the light emitting layer.
In this specification, the electron feature refers to a feature that can accept electrons when an electric field is applied and is attributed to a conductive feature according to the Lowest Unoccupied Molecular Orbital (LUMO) level, electrons formed in the cathode are easily injected into and transported in the light emitting layer.
Arylamine compounds of the general formula (1)
The invention provides an arylamine compound shown in a general formula (1):
R、R 1 、R 0 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted 5-30 membered heteroaryl group having at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom, wherein R, R 1 、R 0 And only two of them are represented by hydrogen atoms and deuterium atoms;
R 5 represented by phenyl, naphthyl or biphenyl;
R 4 represented by hydrogen atom, deuterium atom, aryl group having 6-30 ring-forming carbon atoms, 5-30 membered heteroaryl group having at least one hetero atom selected from oxygen atom, sulfur atom or nitrogen atom, wherein R 4 The connection mode with the general formula (1) comprises two modes of ring combination and substitution;
R 2 、R 3 each independently represented by the structure shown below;
L 1 、L 2 each independently represents a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group;
R 6 、R 7 each independently is represented by a hydrogen atom, a deuterium atom, an aryl group having 6 to 30 ring-forming carbon atoms, a 5-to 30-membered heteroaryl group having at least one hetero atom selected from an oxygen atom, a sulfur atom or a nitrogen atom, wherein R 6 、R 7 The connection mode of (a) is two modes of parallel ring and substitution;
wherein the substituents are selected from deuterium atoms, phenyl groups, naphthyl groups or biphenyl groups.
In a preferred embodiment of the present invention, in formula (1)
R、R 0 Represented as a hydrogen atom;
R 1 represented by phenyl, naphthyl, biphenyl, terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl;
L 1 、L 2 Each independently is represented by a direct bond or phenylene;
the substituent is selected from deuterium atom, phenyl or naphthyl.
In a preferred embodiment of the present invention, in formula (1)
R 1 、R 0 Represented as a hydrogen atom;
r represents phenyl, naphthyl, biphenyl, terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl;
L 1 、L 2 represented independently as direct bond or phenyleneA base;
the substituent is selected from deuterium atom, phenyl or naphthyl.
In a preferred embodiment of the present invention, in formula (1)
R 1 R represents a hydrogen atom;
R 0 represented by phenyl, naphthyl, biphenyl, terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl;
L 1 、L 2 each independently is represented by a direct bond or phenylene;
the substituent is selected from deuterium atom, phenyl or naphthyl.
In a preferred embodiment of the present invention, in formula (1)
R 4 Represented by phenyl, and R 4 The connection mode with the general formula (1) is parallel ring connection.
In a preferred embodiment of the present invention, in formula (1)
R 4 Represented as benzofuranyl, and R 4 The connection mode with the general formula (1) is parallel ring connection.
Preferred examples of the arylamine compounds of the general formula (1) of the present invention include, but are not limited to, the following:
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in a more preferred embodiment of the present invention, the arylamine compound of formula (1) may be selected from any one of the following compounds:
organic electroluminescent device
The invention provides an organic electroluminescent device using aromatic amine compounds of the general formula (1).
In one exemplary embodiment of the present invention, an organic electroluminescent device may include an anode, a hole transport region, a light emitting region, an electron transport region, and a cathode. The organic electroluminescent device may be prepared by conventional methods and materials for preparing the organic electroluminescent device, except for using the aromatic amine-type compound of the present invention in the organic electroluminescent device.
In a preferred embodiment of the present invention, the hole transporting region comprises an arylamine compound of formula (1). Preferably, the hole transport region includes a hole injection layer, a first hole transport layer, and a second hole transport layer. More preferably, the first hole transport layer and the hole injection layer comprise an arylamine compound of formula (1). More preferably, the first hole transport layer is composed of an arylamine compound of the general formula (1), and the hole injection layer is composed of an arylamine compound of the general formula (1) and other doping materials conventionally used for hole injection layers. Advantageously, the hole injection layer and the first hole transport layer consist of conventional materials for hole injection layers and first hole transport layers, and the second hole transport layer consists of an arylamine compound of formula (1). More advantageously, the first hole transport layer and the second hole transport layer are composed of an arylamine compound of formula (1), an arylamine compound of formula (1) and other doping materials conventionally used for hole injection layers.
The organic electroluminescent device of the present invention may be a bottom-emission organic electroluminescent device, a top-emission organic electroluminescent device, and a stacked organic electroluminescent device, and is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as transparent glass or transparent plastic substrates; an opaque substrate such as a silicon substrate; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency. The use direction of the substrate is different according to the property of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
Anode
Preferably, the anode may be formed on the substrate. In the present invention, the anode and the cathode are opposite to each other. The anode may be made of a conductor, such as a metal, metal oxide, and/or conductive polymer, having a higher work function to aid in hole injection. The anode may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, silver, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and metal oxides, such as ZnO with Al or SnO 2 Sb, or ITO and Ag; conductive polymers such as poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene) (PEDOT), polypyrrole, and polyaniline, but are not limited thereto. The thickness of the anode depends on the material used, and is generally 50 to 500nm, preferably 70 to 300nm, and more preferably 100 to 200nm.
Cathode electrode
The cathode may be made of a conductor with a lower work function to aid in electron injection and may be, for example, a metal, metal oxide, and/or conductive polymer. The cathode may be, for example, a metal or alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, and combinations thereof; multilayer structural materials, such as LiF/Al, li 2 O/Al, liF/Ca and BaF 2 /Ca, but is not limited thereto. The thickness of the cathode is generally 10-50nm, preferably 15-20nm, depending on the material used.
Light emitting region
In the present invention, the light emitting region may be disposed between the anode and the cathode, and may include at least one host material and at least one guest material. As the host material and the guest material of the light-emitting region of the organic electroluminescent device of the present invention, a light-emitting layer material for an organic electroluminescent device known in the art can be used. The host material may be, for example, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or 4,4' -bis (9-Carbazolyl) Biphenyl (CBP). Preferably, the host material may comprise anthracene groups. The guest material may be, for example, quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives or aminostyrene derivatives.
In a preferred embodiment of the invention, one or two host material compounds are contained in the light-emitting region.
In a preferred embodiment of the invention, two host material compounds are included in the light emitting region, and the two host material compounds form an exciplex.
In a preferred embodiment of the invention, the host material of the light-emitting region used is selected from one or more of the following compounds H-1 to H-24:
in the present invention, the light emitting region may include a phosphorescent or fluorescent guest material to improve fluorescence or phosphorescence characteristics of the organic electroluminescent device. Specific examples of phosphorescent guest materials include metal complexes of iridium, platinum, and the like. For example, ir (ppy) may be used 3 [ fac-tris (2-phenylpyridine) iridium]Green phosphor materials, blue phosphor materials such as FIrpic and FIr6, and red phosphor materials such as Btp2Ir (acac). For the fluorescent guest material, those generally used in the art can be used. In a preferred embodiment of the present invention, the guest material of the light-emitting film layer used is selected from one of the following compounds D-1 to D-23:
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in the light-emitting region of the present invention, the ratio of host material to guest material used is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
In the light emitting region of the present invention, the host material may also be mixed with a small amount of a dopant, which may be an organic compound or a metal complex, such as Al that emits fluorescence by singlet excitation, to produce light emission; or a material such as a metal complex that emits light by being excited into a triplet state or more by a multiple state. The dopant may be, for example, an inorganic compound, an organic compound, or an organic/inorganic compound, and one or more kinds thereof may be used.
Examples of dopants may be organometallic compounds comprising Ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or combinations thereof. The dopant may be, for example, a compound represented by the following formula (Z), but is not limited thereto:
L 2 MX type (Z))
Wherein,
m is a metal, and is a metal,
L 2 identical or different to X and is a ligand forming a complex with M.
In one embodiment of the invention, M may be, for example, ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or a combination thereof, and L 2 And X may be, for example, a bidentate ligand.
The thickness of the light emitting region of the present invention may be 10 to 50nm, preferably 15 to 40nm, but the thickness is not limited to this range.
Hole transport region
In the organic electroluminescent device of the present invention, a hole transport region is disposed between the anode and the light emitting region, and includes a hole injection layer, a first hole transport layer, and a second hole transport layer.
Hole injection layer
The hole injection material used in the hole injection layer (also referred to as an anode interface buffer layer) is a material capable of sufficiently accepting holes from the anode at a low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. In a preferred embodiment of the present invention, the hole injection layer is a mixed film of host organic material and P-type dopant material. In order to enable holes to be smoothly injected into the organic film layer from the anode, the HOMO energy level of the main organic material and the P-type doping material must have certain characteristics, so that the occurrence of a charge transfer state between the main material and the doping material is expected to be realized, ohmic contact between the hole injection layer and the anode is realized, and efficient injection of holes from the electrode to the hole injection layer is realized. This feature is summarized as: the difference between the HOMO energy level of the host material and the LUMO energy level of the P-type doped material is less than or equal to 0.4eV. Therefore, for hole host materials with different HOMO energy levels, different P-type doping materials are required to be selected to be matched with the hole host materials, so that ohmic contact of an interface can be realized, and the hole injection effect is improved.
Specific examples of the hole injection host organic material include: metalloporphyrin, oligothiophene, arylamine organic materials, hexanitrile hexaazabenzophenanthrene, quinacridone organic materials, perylene organic materials, anthraquinone, polyaniline and polythiophene conductive polymers, but are not limited thereto. More preferably, the hole injection host organic material is selected from the group consisting of arylamine compounds described by general formula (1).
Preferably, the P-type dopant material is a compound having charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4"- ((1 e,1' e,1" e) -cyclopropane-1, 2, 3-trimethylenetris (cyanoformylidene)) tris (2, 3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
In a preferred embodiment of the invention, the P-type doping material used is selected from any of the following compounds HI-1 to HI-10:
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in one embodiment of the invention, the ratio of host organic material to P-type dopant material used is 99:1 to 95:5, preferably 99:1 to 97:3, on a mass basis.
The thickness of the hole injection layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Hole transport layer
In the organic electroluminescent device of the present invention, a hole transport layer may be disposed over the hole injection layer. The hole transport layer includes a first hole transport layer and a second hole transport layer. The hole transport material is suitably a material having a high hole mobility, which can accept holes from the anode or the hole injection layer and transport the holes into the light emitting layer. Specific examples thereof include: arylamine organic materials, conductive polymers, block copolymers having both conjugated and unconjugated portions, and the like, but are not limited thereto.
In a preferred embodiment, the hole transport layer comprises the same arylamine compound of the present invention as the host organic material of the hole injection layer. In another preferred embodiment, the first hole transport layer material is the same as the hole injection layer host organic material, both being arylamine compounds of the present invention. In a more preferred embodiment, the first hole transport layer comprises or consists of the arylamine compound of the present invention. In a preferred embodiment, the second hole transport layer has a different organic compound than the first hole transport layer. In another preferred embodiment, the second hole transport layer consists of carbazole-based arylamine derivatives. Preferably, the compound of the second hole transport layer may be any one of the following compounds:
In a preferred embodiment, both the hole injection layer and the first hole transport layer are composed of materials conventionally used in the art for this purpose, and the second hole transport layer comprises or consists of the arylamine compound of the present invention. In a preferred embodiment, the first hole transport layer material is the same as the hole injection layer host organic material, both being the arylamine compounds of the present invention, and the second hole transport layer comprises or consists of the arylamine compounds of the present invention.
The thickness of the hole transport layer (sum of the thicknesses of the first hole transport layer and the second hole transport layer) of the present invention may be 80 to 200nm, preferably 100 to 150nm, but the thickness is not limited to this range. Preferably, the thickness of the first hole transport layer may be 100 to 150nm, preferably 115 to 125nm; the thickness of the second hole transport layer is 5 to 50nm, preferably 5 to 20nm, more preferably 5 to 10nm.
The invention does not negate the substrate collocation principle of the traditional hole materials, but further superposes on the basis of physical parameters of traditional material screening, namely, the effect of HOMO energy level, carrier mobility, film phase stability, heat-resistant stability of the materials and the like on the hole injection efficiency of the organic electroluminescent device is admitted. On the basis, the material screening conditions are further increased, and further, the selection accuracy of the materials for preparing the high-performance organic electroluminescent device is improved by selecting more excellent organic electroluminescent materials to be used for matching devices.
Electron transport region
In the organic electroluminescent device of the present invention, an electron transport region is disposed between the light emitting region and the cathode, and includes an electron transport layer and an electron injection layer, but is not limited thereto.
Electron injection layer
The electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
Electron transport layer
The electron transport layer may be disposed over the light emitting film layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, those known in the art for use in organic electroluminescent devices can be used Electron transport layer materials, e.g. in Alq 3 Metal complexes of hydroxyquinoline derivatives represented by BAlq and LiQ, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS No.: 1459162-51-6), and 2- (4- (9, 10-bis (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ]]Imidazole derivatives such as imidazole (CAS number 561064-11-7, commonly known as LG 201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, or combinations thereof. Preferably, the electron transport layer material is a mixed film layer of LG201 and LiQ, wherein the mass ratio of LG201 to LiQ is 50:50.
In a preferred organic electroluminescent device of the present invention, the electron transport layer comprises an azacyclic derivative of the general formula (2):
wherein the method comprises the steps of
Ar 1 、Ar 2 And Ar is a group 3 Independently of one another, represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms selected independently of each other from N, O or S;
l represents a single bond, substituted or unsubstituted C 6 -C 30 Arylene, a substituted or unsubstituted 5-30 membered heteroarylene containing one or more heteroatoms, each independently selected from N, O or S;
n represents 1 or 2, preferably 1;
X 1 、X 2 、X 3 independently of one another, N or CH, provided that X 1 、X 2 、X 3 Wherein at least one group of the group represents N.
Preferably, the aza-heterocyclic compound of the general formula (2) is represented by the general formula (2-1):
wherein Ar is 1 、Ar 2 、Ar 3 、X 1 、X 2 、X 3 Each of L is as defined above.
In a preferred embodiment of the present invention, the electron transport layer comprises any one of the following compounds selected from:
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in a more preferred embodiment of the present invention, the electron transport layer comprises any one of the following compounds selected from:
preferably, the electron transport layer of the present invention is a mixed film layer of the compound of formula (2) and LiQ, wherein the mass ratio of the compound of formula (2) to the LiQ is 50:50.
The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm and more preferably 25 to 45nm, but the thickness is not limited to this range.
Cover layer
In order to improve the light-emitting efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be further added to the cathode of the device. According to the optical absorption and refraction principles, the higher the refractive index of the CPL cover layer material is, the better the CPL cover layer material is, and the smaller the light absorption coefficient is, the better the CPL cover layer material is. Any material known in the art may be used as the CPL layer material, such as Alq3, or N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-3-carbazolyl) biphenyl-4, 4' -diamine. The CPL coating typically has a thickness of 5-300nm, preferably 20-100nm and more preferably 40-80nm.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
Hereinafter, an organic electroluminescent device according to an embodiment of the present invention is described.
The organic electroluminescent device may be any element that converts electric energy into light energy or converts light energy into electric energy without particular limitation, and may be, for example, an organic electroluminescent device, an organic light emitting diode, an organic solar cell, and an organic photoconductor. Herein, the organic light emitting diode is described as one example of an organic electroluminescent device (but the present invention is not limited thereto), and may be applied to other organic electroluminescent devices in the same manner.
In the drawings, the thickness of layers, films, substrates, regions, etc. are exaggerated for clarity. Like numbers refer to like elements throughout. It will be understood that when an element such as a layer, film, region or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
Fig. 1 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
Referring to fig. 1, an organic light emitting diode 30 according to an embodiment of the present invention includes an anode 1 and a cathode 8 opposite to each other, a hole transport region 10, a light emitting region 5, and an electron transport region 20 sequentially disposed between the anode 1 and the cathode 8, and a capping layer 9 disposed over the cathode, wherein the hole transport region 10 includes a hole injection layer 2, a first hole transport layer 3, and a second hole transport layer 4, and the electron transport region 20 includes an electron transport layer 6 and an electron injection layer 7.
The invention also relates to a method of manufacturing an organic electroluminescent device comprising sequentially laminating an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, the respective layers are preferably formed by a vacuum vapor deposition method. The individual process conditions in the vacuum evaporation process can be routinely selected by those skilled in the art according to the actual needs.
The material for forming each layer according to the present application may be used as a single layer by forming a film alone, or may be used as a single layer by forming a film after mixing with another material, or may be a laminated structure between layers formed by forming a film alone, a laminated structure between layers formed by mixing, or a laminated structure between layers formed by forming a film alone and layers formed by mixing.
The application also relates to a display device comprising the organic electroluminescent device of the application. Preferably, the present application relates to a full color display device, in particular a flat panel display device, having three pixels of red, green and blue comprising the organic electroluminescent device of the present application. The display device may further include at least one thin film transistor. The thin film transistor may include a gate electrode, source and drain electrodes, a gate insulating layer, and an active layer, wherein one of the source and drain electrodes may be electrically connected to an anode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, but is not limited thereto.
Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used in a generic and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art as the present disclosure proceeds, features, characteristics, and/or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics, and/or elements described in connection with other embodiments unless specifically indicated. Accordingly, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the application.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
Examples
Unless otherwise indicated, the various materials used in the following examples and comparative examples are commercially available or may be obtained by methods known to those skilled in the art.
Preparation of the Compounds of formula (1)
Example 1: synthesis of Compound H11
In a three-necked flask, under the protection of nitrogen gas, 0.01mol of raw material A,0.012mol of raw material B,0.02mol of sodium carbonate and a mixed solvent (150 ml of toluene, 45ml of H were added 2 O) and then 1X 10 is added -4 mol tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 Heating to 105 ℃, refluxing and reacting for 24 hours, sampling the spot plate, and displaying no iodine compound remained, and completely reacting. Naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation (-0.09 MPa,85 ℃) on the filtrate, and passing through a neutral silica gel column (silica gel 100-200 meshes, and eluent is chloroform: n-hexane=1:2 (volume ratio)) to obtain an intermediate M. Elemental analysis structure (molecular formula C) 24 H 15 BrClN): theoretical value C66.61; h3.49; cl 8.19; br 18.46; n3.24; test value: c66.57; h3.45; cl 8.14; br 18.53; n3.31. MS: theoretical 431.01 and measured 431.19.
In a three-necked flask, under the protection of nitrogen gas, 0.01mol of intermediate M,0.012mol of raw material C,0.02mol of sodium carbonate and a mixed solvent (150 ml of toluene, 45ml of H were added 2 O) and then 1X 10 is added -4 mol tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 Heating to 105 ℃, refluxing and reacting for 24 hours, sampling the spot plate, and displaying no bromide to remain, wherein the reaction is complete. Naturally cooling to room temperature, filtering, and performing reduced pressure rotary evaporation on the filtrate0.09MPa,85 ℃) and passing through a neutral silica gel column (silica gel 100-200 meshes, wherein the eluent is chloroform: n-hexane=1:2 (volume ratio)), to give intermediate P. Elemental analysis structure (molecular formula C) 54 H 37 ClN 2 ): theoretical value C86.55; h4.98; cl 4.73; n3.74; test value: c86.59; h4.91; cl 4.75; n3.72. MS: theoretical 748.26 and measured 748.05.
In a three-necked flask, under the protection of nitrogen gas, 0.01mol of intermediate P,0.012mol of raw material D,0.02mol of sodium carbonate and a mixed solvent (150 ml of toluene, 45ml of H were added 2 O) and then 1X 10 is added -4 mol tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 Heating to 105 ℃, refluxing and reacting for 24 hours, sampling the spot plate, and displaying no chloride residue and complete reaction. Naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation (-0.09 MPa,85 ℃) on the filtrate, and passing through a neutral silica gel column (silica gel 100-200 meshes, and eluting with chloroform: n-hexane=1:2 (volume ratio)) to obtain the target compound H11. Elemental analysis structure (molecular formula C) 60 H 42 N 2 ): theoretical value C91.11; h5.35; n3.54; test value: c91.06; h5.31; n3.62. MS: theoretical 790.33 and measured 790.48.
The following compounds (starting materials used were all supplied from medium energy saving Mo Run) were prepared in the same manner as in example 1, and the synthetic starting materials are shown in table 1 below. The synthesis of the hole transport layer material used in the present invention is described in patent CN110577511a, the raw materials used are all provided by the intermediate energy saving Mo Run.
TABLE 1
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Testing of Compounds of formula (1)
Glass transition temperature Tg: the temperature was increased at a rate of 10℃per minute as measured by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter).
HOMO energy level: the test was performed by an ionization energy measurement system (IPS 3) test, which was a vacuum environment.
Eg energy level: based on the tangent line between the ultraviolet spectrophotometry (UV absorption) baseline of the single material film and the ascending side of the first absorption peak, the value of the intersection point between the tangent line and the baseline is calculated.
Hole mobility: the material was fabricated as a single charge device, measured using space charge (induced) limited amperometry (SCLC).
Triplet energy level T1: the material was dissolved in toluene and tested by a Hitachi F4600 fluorescence spectrometer.
The specific physical properties are shown in Table 2.
TABLE 2
As can be seen from the data in table 2 above, the compounds of the present application have suitable HOMO levels, higher hole mobility and wider band gap (Eg), and can realize organic electroluminescent devices having high efficiency, low voltage and long lifetime.
III device preparation examples
The compound of the present application is used below by taking a top-emission organic electroluminescent device as an example, but the present application is not limited thereto.
The molecular structural formula of the materials involved in the following preparation process is shown as follows:
comparative example 1
The organic electroluminescent device is prepared according to the following steps:
a) Using transparent glass as a substrate, washing an anode layer (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)) thereon, ultrasonically cleaning with deionized water, acetone and ethanol for 15 minutes, respectively, and then treating in a plasma cleaner for 2 minutes;
b) On the washed anode layer, hole transport material HT1 and P-type doped material HI1 are respectively placed in two evaporation sources under vacuum degree of 1.0E -5 Controlling the evaporation rate of the compound HT1 to be under Pa pressureThe evaporation rate of the P-type doping material HI1 is controlled to be +.>Co-steaming to form a hole injection layer with the thickness of 10nm;
c) Evaporating a first hole transport layer on the hole injection layer by vacuum evaporation, wherein the hole transport layer is made of a compound HT1, and the thickness is 120nm;
d) Evaporating a second hole transport layer B-1 on the first hole transport layer by vacuum evaporation, wherein the thickness of the second hole transport layer B-1 is 10nm;
e) Evaporating a luminescent layer material on the second hole transport layer by vacuum evaporation, wherein the host material is H-1, the guest material is D-1, the mass ratio is 97:3, and the thickness is 20nm;
f) On the light emitting layer, ET1 and LiQ, ET1 were evaporated by vacuum evaporation: the mass ratio of LiQ is 50:50, the thickness is 30nm, and the LiQ is used as an electron transport layer;
g) Evaporating LiF on the electron transport layer by vacuum evaporation, wherein the thickness of the LiF is 1nm, and the layer is an electron injection layer;
h) Vacuum evaporating an Mg-Ag (1:1) electrode layer with the thickness of 16nm on the electron injection layer, wherein the electrode layer is a cathode layer;
i) CPL material CPL-1 is vacuum evaporated on the cathode layer, and the thickness is 70nm.
Comparative examples 2 to 22
The procedure of device preparation example 1 was followed, except that the organic materials in steps b), c), d), and f) were replaced with the organic materials shown in Table 3, respectively, wherein the ratios of ET1: liQ, E2: liQ, E5: liQ, E12: liQ, E16: liQ, E23: liQ were 50:50.
Comparative examples 23 to 26
The procedure of comparative example 1 was followed, substituting the organic materials in steps b), c), d), and e) with those shown in Table 4, respectively.
Comparative examples 27 to 30
The procedure of comparative example 1 was followed, substituting the organic materials in steps b), c), d), and e) with those shown in Table 5, respectively.
Examples 1 to 113
The procedure of device preparation example 1 was followed, except that the organic materials in steps b), c), d), and f) were replaced with the organic materials shown in Table 3, respectively, wherein the ratios of ET1: liQ, E2: liQ, E5: liQ, E12: liQ, E16: liQ, E23: liQ were 50:50.
Examples 114 to 125
The procedure of comparative example 23 was followed, except that the organic materials in steps b), c), d), and f) were replaced with the organic materials shown in Table 4, respectively.
Examples 126 to 137
The procedure of comparative example 27 was followed, except that the organic materials in steps b), c), d), and f) were replaced with the organic materials shown in Table 5, respectively.
TABLE 3 Table 3
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TABLE 4 Table 4
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TABLE 5
Testing of device Performance
After the OLED light-emitting device was fabricated as described above, the cathode and anode were connected using a well-known driving circuit, and various properties of the device were measured. The results of measuring the performance of the devices of examples 1 to 137 and comparative examples 1 to 30 are shown in tables 6, 7 and 8.
TABLE 6
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TABLE 7
TABLE 8
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Note that: LT95 refers to the time taken for the device brightness to decay to 95% of the original brightness;
The voltage, current efficiency and color coordinates were tested using an IVL (Current-Voltage-Brightness) test system (Freund's scientific instruments, st. John) at 10mA/cm 2 ；
The life test system is an EAS-62C OLED life test system of japan systems research limited.
The high temperature lifetime refers to the time it takes for the device to decay to 80% of its original brightness at 80 ℃.
As can be seen from the results of table 4, the organic electroluminescent device (hereinafter referred to as an inventive device) prepared using the arylamine compound of the present invention as the organic host material of the hole injection layer and simultaneously as the first hole transport layer material has a voltage equivalent to that of the organic electroluminescent device (hereinafter referred to as a comparative device) prepared using other substances (e.g., HT1, HT2, HT3, and HT 4) as the organic host material of the hole injection layer and simultaneously as the first hole transport layer material, however, the inventive device has unexpected technical effects in terms of current efficiency, high temperature lifetime, LT 95. Specifically, under the same conditions, the device (about 159-168 cd/A) of the invention is higher than the comparative device (about 147-155 cd/A) in terms of current efficiency, and is improved by more than about 4%; in the LT95 aspect, the device (about 310-363 Hr) of the invention far exceeds the comparative device (about 265-290 Hr) and is improved by more than 7%; the inventive device (about 906-975 Hr) was far superior to the comparative device (about 810-843 Hr) in terms of high temperature lifetime (LT 80), and improved by more than 7%. It can be seen that under comparable conditions, the inventive device achieves better current efficiency, LT95 and high temperature lifetime than the comparative device at comparable drive voltages, which would not be expected by one skilled in the art.
Furthermore, in the inventive examples, the current efficiency was comparable to that of the devices obtained by collocating the electron transport layer compounds E2, E5, E12, E16, E23 (examples 55-113) with the electron transport layer compounds ET1 (examples 1-54), but with better LT95 (311-340 vs 337-365 Hr) and high temperature lifetime (906-934 vs 937-975 Hr).
As is clear from Table 7, in examples 114 to 125, the composition of the present invention was used as a hole injection layer in a green light device, and the arylamine compound of the general formula (1) or the composition thereof was used as a hole transport layer, and the lifetime was improved by 6% or more.
As is clear from Table 8, in examples 126 to 137, the composition of the present invention was used as a hole injection layer in a red light device, and the arylamine compound of the general formula (1) or the composition thereof was used as a hole transport layer, which improved the efficiency by 10% or more.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the described embodiments. On the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The foregoing embodiments are, therefore, to be construed as illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.
Symbol description
30: organic light emitting diode
1: anode
9: cover layer
8: cathode electrode
7: electron injection layer
6: electron transport layer
5: light emitting region
3: a first hole transport layer
4: a second hole transport layer
2: hole injection layer
10: hole transport region
20: electron transport regions.
Claims (16)
1. An arylamine compound shown in a general formula (1):
wherein the method comprises the steps of
R、R 1 、R 0 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted 5-30 membered heteroaryl group having at least one heteroatom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom, wherein R, R 1 、R 0 And only two of them are represented by hydrogen atoms and deuterium atoms;
R 5 represented by phenyl, naphthyl or biphenyl;
R 4 represented by hydrogen atom, deuterium atom, aryl group having 6-30 ring-forming carbon atoms, 5-30 membered heteroaryl group having at least one hetero atom selected from oxygen atom, sulfur atom or nitrogen atom, wherein R 4 The connection mode with the general formula (1) comprises two modes of ring combination and substitution;
R 2 、R 3 each independently represented by the structure shown below;
L 2 each independently represents a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group;
L 1 Is a direct bond;
R 6 、R 7 represented independently of each other as a hydrogen atom, a deuterium atom, a phenyl group, a biphenyl group, wherein R 6 、R 7 The connection mode of (2) is substitution;
wherein the substituents are selected from deuterium atoms, phenyl groups, naphthyl groups or biphenyl groups.
2. The arylamine compound according to claim 1, wherein
R、R 0 Represented as a hydrogen atom;
R 1 represented by phenyl, naphthyl, biphenyl, terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl;
L 2 is a direct bond or phenylene;
the substituent is selected from deuterium atom, phenyl or naphthyl.
3. The arylamine compound according to claim 1, wherein
R 1 、R 0 Represented as a hydrogen atom;
r represents phenyl, naphthyl, biphenyl, terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl;
L 2 is a direct bond or phenylene;
the substituent is selected from deuterium atom, phenyl or naphthyl.
4. The arylamine compound according to claim 1, wherein
R 4 Represented by phenyl or benzofuranyl, and is connected with the general formula (1) in a parallel ring manner.
5. The arylamine compound of general formula (1) according to claim 1, wherein the arylamine compound of general formula (1) is selected from any one of the following compounds:
6. An organic electroluminescent device comprising, in order from bottom to top, an anode, a hole transporting region, a light emitting region, an electron transporting region, and a cathode, wherein the hole transporting region comprises the arylamine compound of general formula (1) according to any one of claims 1 to 5.
7. The organic electroluminescent device of claim 6, wherein the hole transport region comprises a hole injection layer, a first hole transport layer, and a second hole transport layer.
8. The organic electroluminescent device according to claim 6, wherein the first hole transport layer and the hole injection layer comprise the arylamine compound of general formula (1) according to any one of claims 1 to 5.
9. The organic electroluminescent device according to claim 6, wherein the first hole transport layer consists of the arylamine compound of general formula (1) according to any one of claims 1 to 5, and the hole injection layer consists of the arylamine compound of general formula (1) according to any one of claims 1 to 5 and a doping material.
10. The organic electroluminescent device according to claim 6, wherein the second hole transport layer consists of an arylamine compound of general formula (1) according to any one of claims 1 to 5.
11. The organic electroluminescent device according to claim 6, wherein the first hole transport layer and the second hole transport layer are composed of the arylamine compound of the general formula (1) according to any one of claims 1 to 5, and the hole injection layer is composed of the arylamine compound of the general formula (1) according to any one of claims 1 to 5 and a doping material.
12. The organic electroluminescent device according to claim 6, wherein the electron transport region comprises an aza-heterocyclic compound represented by the following general formula (2):
wherein the method comprises the steps of
Ar 1 、Ar 2 And Ar is a group 3 Independently of one another, represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl containing one or more heteroatoms selected independently of each other from N, O or S;
l represents a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene containing one or more heteroatoms, each independently selected from N, O or S;
n represents 1 or 2;
X 1 、X 2 、X 3 independently of one another, N or CH, provided that X 1 、X 2 、X 3 Wherein at least one group of the group represents N.
13. The organic electroluminescent device according to claim 12, wherein in the general formula (2), n is 1.
14. The organic electroluminescent device according to claim 6, wherein the electron transport region comprises an electron transport layer and an electron injection layer, wherein the electron transport layer comprises the aza-cycle compound of formula (2) according to claim 12 or 13, and the electron injection layer is an N-type metal material.
15. Use of an arylamine compound of general formula (1) according to any one of claims 1-5 as hole transport material in an organic electroluminescent device.
16. A display apparatus comprising the organic electroluminescent device as claimed in any one of claims 6 to 14.
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