CN114516804A - Diamine derivative and organic electroluminescent device using same - Google Patents
Diamine derivative and organic electroluminescent device using same Download PDFInfo
- Publication number
- CN114516804A CN114516804A CN202110121432.8A CN202110121432A CN114516804A CN 114516804 A CN114516804 A CN 114516804A CN 202110121432 A CN202110121432 A CN 202110121432A CN 114516804 A CN114516804 A CN 114516804A
- Authority
- CN
- China
- Prior art keywords
- substituted
- hole transport
- group
- general formula
- organic electroluminescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000004985 diamines Chemical class 0.000 title claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 130
- 230000005525 hole transport Effects 0.000 claims abstract description 77
- -1 furanylene Chemical group 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 70
- 238000002347 injection Methods 0.000 claims description 65
- 239000007924 injection Substances 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 20
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 170
- 239000011799 hole material Substances 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000010408 film Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 15
- 230000008025 crystallization Effects 0.000 description 15
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 239000011368 organic material Substances 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 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 12
- 230000009477 glass transition Effects 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 238000007738 vacuum evaporation Methods 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229910001868 water Inorganic materials 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-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
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 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 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical class 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 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
- 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
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 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
- 230000005284 excitation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000001894 space-charge-limited current method Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 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
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- 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
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710110702 Probable chorismate pyruvate-lyase 1 Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 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
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 159000000006 cesium salts Chemical class 0.000 description 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 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
- 238000007641 inkjet printing Methods 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
- 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
- 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 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
- 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
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 238000004806 packaging method and process Methods 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001681 protective effect Effects 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
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals 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
- 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
- 238000012216 screening Methods 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
- 239000000243 solution Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 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
- 125000005580 triphenylene 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
- 229910001930 tungsten oxide Inorganic materials 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
-
- 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
- H10K85/633—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
- 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
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen 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
- H10K85/654—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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of semiconductors, in particular to a novel diamine derivative with a structure shown in a general formula (1) and application thereof as a hole transport material in an organic electroluminescent device, and relates to an organic electroluminescent device containing the diamine derivative and a display device containing the light emitting device.
Description
Technical Field
The present invention relates to the field of semiconductor technology, and more particularly, to a novel diamine derivative and its use as a hole transport material in an organic electroluminescent device, and to an organic electroluminescent device comprising the same and a display apparatus comprising the same.
Background
Carriers (holes and electrons) in an organic electroluminescent device (OLED) are injected into the device from two electrodes of the device respectively under the driving of an electric field, and meet recombination to 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, as a charge transport material, it is required to have good carrier mobility. The hole injection layer material and the hole transport layer material used in the existing organic electroluminescent device have relatively weak injection and transport characteristics, and the hole injection and transport rate is not matched with the electron injection and transport rate, so that the composite region has large deviation, and the stability of the device is not facilitated. In addition, reasonable energy level matching between 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, and therefore, how to adjust the balance between holes and electrons and adjust the recombination region is an important subject in the field.
Blue organic electroluminescent devices are always soft ribs in the development of full-color OLEDs, and the efficiency, the service life and other properties of blue light devices are difficult to be comprehensively improved at present, so that how to improve the properties of the blue light devices is still a crucial problem and challenge in the field. Most of blue host materials currently used in the market are electron-biased hosts, and therefore, in order to adjust the carrier balance of the light-emitting layer, a hole-transporting material is required to have excellent hole-transporting performance. The better the hole injection and transmission, the more the composite region will shift to the side far away from the electron blocking layer, so as to far away from the interface to emit light, thus improving the performance of the device and prolonging the service life. 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.
Since the hole transport material has a thick film thickness, the heat resistance and amorphousness of the material have a crucial influence on the lifetime of the device. Materials with poor heat resistance are easy to decompose in the evaporation process, pollute the evaporation cavity and damage the service life of devices; the material with poor film phase stability can crystallize 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, the development of stable and efficient hole transport materials for organic electroluminescent devices has not been sufficiently achieved. Therefore, there is a continuous need to develop a new material to better meet the performance requirements of the organic electroluminescent device.
The diamine derivative described in JP1999273860A has a low glass transition temperature (lower than 120 ℃) because two amine groups are directly connected to the middle naphthalene group, and the low glass transition temperature deteriorates the stability of the device at high temperature, and reduces the lifetime of the device, especially at high temperature.
The diamine derivative described in patent document CN101668730A has a problem that the diamine derivative described in the patent document has an unstable film phase due to the connection mode of the two side amine groups and the middle naphthyl group, and the unstable film phase causes instability of the device, which affects the device lifetime, particularly the high temperature lifetime.
Disclosure of Invention
In order to solve the problems, the organic electroluminescent device is made of materials with excellent hole and electron injection/transmission performance, film stability and weather resistance, so that the organic electroluminescent device is beneficial to improving the recombination efficiency of electrons and holes and the utilization rate of excitons, and the obtained device has high efficiency and long service life.
Therefore, the inventor develops a new diamine derivative, naphthyl or naphthyl derivative as a basic skeleton, and the two fixed sites are connected with amine groups, and the connection mode enables the compound of the invention to have higher glass transition temperature and excellent film phase stability. In addition, the present inventors have found that when a hole transport material of an organic electroluminescent device is formed by using the novel diamine derivative, effects such as device lifetime extension can be exhibited.
Accordingly, it is an object of the present invention to provide a novel diamine derivative having the following general formula (1):
wherein
A represents a structure represented by general formula (2) to general formula (8);
L1represented by a direct bond, phenylene, furanylene, naphthylene or biphenylene;
L2represented by a direct bond, phenylene, furanylene, naphthylene or biphenylene;
and when A is represented by the general formula (2) or the general formula (3), L1And L2Not being a direct bond at the same time;
represents L1And R1Can be connected with each other to form a ring, or can be disconnected with each other; when L is1And R1When interconnected to form a ring, L1、R1Together with N to form a substituted or unsubstituted carbazolyl group, preferably N-benzeneCarbazolyl group;
R1to R4Independently represent hydrogen, substituted or unsubstituted aryl with 6-30 ring carbon atoms, and substituted or unsubstituted 5-30 membered heteroaryl, wherein the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom, and when A represents a structure represented by general formula (2) or general formula (3), R represents1To R4Not simultaneously represented as phenyl;
wherein the substituents having a group in substituted form are optionally selected from deuterium atom, C1-C6Alkyl, phenyl, naphthyl, biphenyl, carbazolyl, N-phenylcarbazolyl, adamantyl, thienyl, phenylthienyl, furyl, phenylfuryl, benzofuryl or dibenzofuryl. Preferably, C1-C6The alkyl group is preferably methyl, ethyl, propyl, isopropyl and/or tert-butyl, more preferably C1-C6The alkyl group is a tert-butyl group.
Preferably, when the above-mentioned groups, preferably phenyl groups, are substituted by C1-C6When alkyl is substituted, C1-C6The alkyl substituent is located para to the group, preferably phenyl.
It is another object of the present invention to provide the use of the diamine derivatives of formula (1) as hole transport materials in organic electroluminescent devices, preferably the use of said compounds in blue organic electroluminescent devices.
It is another object of the present invention to provide an organic electroluminescent device having improved luminous efficiency and lifespan, which comprises an anode, a hole transporting region, a light emitting region, an electron transporting region, and a cathode in this order, wherein the hole transporting region comprises the diamine derivative of the general formula (1) according to the present invention.
It is also an object of the present invention to provide a full color display apparatus including three pixels of red, green and blue, the full color display apparatus including the organic electroluminescent device of the present invention. Preferably, the present invention also provides a blue display device comprising the compound of the present invention as a hole transport material. Preferably, the invention also provides a full-color display device comprising three pixels of red, green and blue, wherein the full-color display device comprises a red organic electroluminescent device, a blue organic electroluminescent device and a green organic electroluminescent device, and the devices of the three pixels of red, green and blue have a common hole injection layer and a first hole transport layer. Preferably, the present invention further provides a full-color display device including three red, green and blue pixels, wherein the devices of the three red, green and blue pixels have a common hole injection layer and a first hole transport layer, and the second hole transport layer of the device of the blue pixel is a common layer.
Advantageous effects
The diamine derivative, naphthyl or naphthyl derivative is used as a basic skeleton, and fixed sites at two sides are connected with amino groups, so that the compound has higher glass transition temperature, and the higher glass transition temperature is favorable for excellent stability of devices in manufacturing and high-temperature environments, thereby prolonging the service life of the devices, especially the service life at high temperature.
The compound can form a stable electron transfer state (CT state) with P doping, so that a hole injection layer and an anode interface form good ohmic contact, space charge limited current is formed, injection of carriers is promoted, the exciton concentration of a light-emitting layer is improved, and the efficiency of a device 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 is reduced, a space charge limited current region can be reached under a lower driving voltage, and the efficiency of the device is effectively improved.
In addition, the arylamine compound is combined with the nitrogen heterocyclic electron transport material, so that electrons and holes are in an optimal balance state, and the arylamine compound has higher efficiency and excellent service life, particularly the high-temperature service life of a device.
Drawings
Fig. 1 schematically shows a schematic cross-sectional view of an organic electroluminescent device 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 denotes 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 represented as a cathode; 9 denotes a cover layer; and 30, an organic electroluminescent device.
In the drawings, the thickness of layers, films, substrates, regions, etc. are exaggerated for clarity. Like reference numerals refer to like elements throughout the specification.
FIG. 2 is a graph comparing the surface morphology of the materials of the compounds H1, H20, H136, H257 of the present invention and the conventional compounds HT3-HT6 in the film crystallization experiment.
FIG. 3 is the nuclear magnetic hydrogen spectrum of compound H1.
Detailed Description
Definition of
In the present invention, unless otherwise specified, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule. Further, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between the energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level is, the lower the energy of the energy level is.
In this specification, the term "substituted" means that one or more hydrogen atoms on the designated atom or group are replaced with the designated group, provided that the designated atom's normal valency is not exceeded in the present case.
In this specification, the term "C6-C30Aryl "or" aryl having 6 to 30 ring carbon atoms "refers to a monovalent group of a fully unsaturated monocyclic, polycyclic or fused polycyclic (i.e., rings sharing a pair of adjacent carbon atoms) system having 6 to 30 ring carbon atoms, examples of which include, but are not limited to, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, biphenylyl, terphenyl, m-terphenyl, anthryl, pyrenyl, terphenyl, p-terphenyl, m-terphenyl, anthryl, phenanthryl, and the like,
Radical, bia threePhenyl group, perylene group, indenyl group, triphenylene group, fluorene group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, spirobifluorenyl group, group in which phenyl group and spirobifluorenyl group are condensed,
And the like. "C6-C30Arylene "is a divalent group of a fully unsaturated monocyclic, polycyclic, or fused polycyclic (i.e., rings that share a pair of adjacent carbon atoms) system having 6 to 30 ring carbon atoms, examples of which include, but are not limited to, divalent groups of the foregoing groups.
In this specification, the term "C5-C30Heterocyclyl "refers to a monovalent group of saturated, partially saturated, or fully unsaturated rings having 5 to 30 ring carbon atoms and containing at least one heteroatom selected from N, O and S, including but not limited to heteroaryl, heterocycloalkyl, fused rings, or combinations thereof. When the heterocyclyl is a fused ring, each or all of the rings of the heterocyclyl may contain at least one heteroatom. Said C is5-C30Examples of heterocyclic groups include, but are not limited to, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothienyl, benzimidazolyl, indolyl, quinolyl, isoquinolyl, quinazolinyl, quinolinyl, naphthyridinyl, benzoxazinyl, benzothiazinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, dibenzothienyl, carbazolyl, phenylfuranyl, dibenzofuranyl, N-phenylcarbazolyl, N-naphthylcarbazolyl, N-biphenylcarbazolyl, N-bithenylcarbazolyl, N-phenylcarbazolyl, 9-diphenylfluorenyl, dimethylfluorenyl, fluorenyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, benzoxazinyl, dibenzothienyl, carbazolyl, carboxalyl, carbobenzofuranyl, carbazolyl, phenylcarbazolyl, 9-diphenylfluorenyl, dimethylfluorenyl, and the like,
And the like. "C5-C30Heterocyclylene "is a compound having 5 to 30 ring carbon atoms and containing at least one ring carbon atom selected from N, O toAnd a saturated, partially saturated or fully unsaturated ring of the heteroatom of S, examples of which include, but are not limited to, divalent groups of the above groups.
"5-30 membered heteroaryl" means an aromatic monovalent group having 5 to 29 ring carbon atoms and at least one heteroatom selected from N, O and S, examples of which include, but are not limited to, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothienyl, benzimidazolyl, indolyl, quinolyl, isoquinolyl, quinazolinyl, quinolyl, naphthyridinyl, benzoxazinyl, benzothiazinyl, acridinyl, phenazinyl, phenothiazinyl, oxarphinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.
C6-C30Aryl or aryl having 6 to 30 ring-forming carbon atoms and C6-C30Arylene group "," C5-C30Heterocyclic group "," C5-C30Heterocyclylene "," 5-to 30-membered heteroaryl "may be unsubstituted or may be substituted with: deuterium, phenyl, biphenyl, naphthyl, benzofuranyl, dibenzofuranyl, and the like.
Arylamine compounds of general formula (1)
The invention provides a diamine derivative, which has a structure shown in a general formula (1) as follows:
wherein
A represents a structure represented by general formula (2) to general formula (8);
L1represented by a direct bond, phenylene, furanylene, naphthylene or biphenylene;
L2represented by a direct bond, phenylene, furanylene, naphthylene or biphenylene;
and when A is represented by the general formula (2) or (3), L1And L2Not being a direct bond at the same time;
represents L1And R1Can be connected with each other to form a ring, or can be disconnected with each other; when L is1And R1When interconnected to form a ring, L1、R1And N together form a substituted or unsubstituted carbazolyl group, preferably an N-phenylcarbazolyl group;
R1to R4Independently represent hydrogen, substituted or unsubstituted aryl with 6-30 ring carbon atoms, substituted or unsubstituted 5-30 membered heteroaryl, wherein the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom, and when A represents the structure shown in the general formula (2) or the general formula (3), R represents1To R4Not simultaneously represented as phenyl;
preferably, R1To R4Each independently represents hydrogen or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthryl, pyrenyl, spirobifluorenyl, naphthylphenyl, phenylnaphthyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, and the like, furyl, benzofuryl, carbazolyl, N-phenylcarbazolyl, thienyl, benzophenanthryl, benzofuryl-phenyl, phenyl-furyl-phenyl, dibenzofuryl, and the like;
wherein the substituents having a group in substituted form are optionally selected from deuterium atom, C1-C6Alkylphenyl, naphthyl, biphenyl, carbazolyl, N-phenylcarbazolyl, adamantyl, thienyl, phenylthienyl, furyl, phenylfuryl, benzofuryl or dibenzofuryl; preferably, C1-C6The alkyl group is preferably methyl, ethyl, propyl, isopropyl and/or tert-butyl, more preferably C1-C6The alkyl group is a tert-butyl group.
Preferably, when the above-mentioned groups, preferably phenyl groups, are substituted by C1-C6When substituted by alkyl, C1-C6Alkyl substituents located on said group, preferablyPara to the phenyl group.
In a preferred embodiment of the present invention, wherein
A represents a structure represented by general formula (4) to general formula (8);
L1represented by phenylene, furanylene, naphthylene or biphenylene;
the remaining groups and symbols are as described above.
In a more preferred embodiment of the present invention, wherein
A represents a structure represented by general formula (4) to general formula (8);
L1and L2Each represented by phenylene, furanylene, naphthylene, or biphenylene;
the remaining groups and symbols are as described above.
In a particular embodiment of the present invention, the diamine derivative has a structure of the following general formula (1-1):
wherein
A、L2、R2To R4As defined in formula (1). Preferably, in the formula (1-1), R2Is hydrogen or phenyl. Particularly preferably, L2Is phenylene. More preferably, in the formula (1-1), R3To R4Each independently represents a substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, phenanthryl group, pyrenyl group, spirobifluorenyl group, naphthylphenyl group, phenylnaphthyl group, 9 '-dimethylfluorenyl group, 9' -diphenylfluorenyl group, etc., furyl group, benzofuryl group, carbazolyl group, N-phenylcarbazolyl group, thienyl group, benzophenanthryl group, benzofuryl-phenyl group, phenyl-furyl-phenyl group, dibenzofuryl group, etc., wherein when the above groups are in substituted form, the substituents are as described above.
In a preferred embodiment of the present invention, in the general formula (1),
a represents a structure represented by general formula (2) or general formula (3);
L1、L2each independently represents a direct bond, phenylene, biphenylene or furanylene, and L1、L2Not being a direct bond at the same time; or L2Represented by a direct bond, phenylene or furanylene, L1、R1And N together form a substituted or unsubstituted carbazolyl group, preferably an N-phenylcarbazolyl group; in a particular embodiment, L2Is represented by phenylene, L1、R1And N together form a substituted or unsubstituted carbazolyl group, preferably an N-phenylcarbazolyl group;
R1to R4As defined in formula (1), and R1To R4Is not phenyl at the same time;
when the above groups are in substituted form, the substituents are as described above.
In another embodiment of the present invention, in the general formula (1), a represents a structure represented by one of general formulae (4) to (8);
L1、L2each independently represents a direct bond, a phenylene group or a furanylene group, preferably each independently represents a direct bond or a phenylene group; or L2Represented by a direct bond, phenylene or furanylene, L1、R1And N together form a substituted or unsubstituted carbazolyl group, preferably an N-phenylcarbazolyl group.
Preferred specific examples of the aromatic amine-based compound of the present invention include, but are not limited to, the following compounds:
in a more preferred embodiment of the present invention, the aniline compound may be selected from the following compounds: (H1) (H2), (H8), (H13), (H14), (H15), (H19), (H20), (H25), (H31), (H34), (H37), (H51), (H56), (H67), (H75), (H84), (H94), (H98), (H105), (H109), (H114), (H118), (H130), (H136), (H257), (H262), (H286), (H316), (H327), (H473), (H489), (H520), (H543), (H544), or (H553).
Organic electroluminescent device
The present invention provides an organic electroluminescent device comprising a diamine derivative of the general formula (1).
The organic electroluminescent device may be any element that converts electrical energy into light energy or converts light energy into electrical energy without particular limitation, and may be, for example, an organic light emitting diode. Herein, the organic light emitting diode is described as one example of the 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 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. In addition to using the aromatic amine-based compound of the present invention in the organic electroluminescent device, the organic electroluminescent device can be prepared by conventional methods and materials for preparing organic electroluminescent devices.
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, which is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use varies depending on the nature 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 opposed to each other. The anode may be made using materials conventionally used in the art. Preferably, the anode may be made of a conductor having a high work function to aid hole injection, such as a metal, metal oxide and/or conductive polymer. Specifically, the anode may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, silver, or an alloy thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals with metal oxides, e.g. ZnO with Al or SnO2And Sb, or ITO and Ag; conductive polymerCompounds such as poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thiophene) (PEDOT), polypyrrole, and polyaniline, or combinations of the above materials, but are not limited thereto. The thickness of the anode depends on the material used and is typically 50-500nm, preferably 70-300nm, and more preferably 100-200 nm.
Cathode electrode
The cathode may be made using materials conventionally used in the art. Preferably, the cathode may be made of a conductor having a low work function to aid in electron injection, and may be, for example, a metal oxide, and/or a conductive polymer. Specifically, 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; materials of multilayer structure, e.g. LiF/Al, Li2O/Al, LiF/Ca and BaF2Ca, or a combination of the above materials, but not limited thereto. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20 nm.
Light emitting area
In the present invention, the light emitting region includes a light emitting layer, which may be disposed between an anode and a cathode, wherein the light emitting layer 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, light emitting layer materials for organic electroluminescent devices known in the art can be used. According to one embodiment of the present application, the compound of the present invention can be used for organic electroluminescent devices of blue, red, green, yellow and other colors, wherein the blue organic electroluminescent device is preferred, and thus, according to the present invention, the light emitting layer material can be a blue light emitting layer material, a red light emitting layer material, a green light emitting layer material, a yellow light emitting layer material and other colors of light emitting layer materials. In a preferred embodiment of the present application, the host material may be a blue light emitting material, such as 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, perylene and its derivatives, benzopyran derivatives, rhodamine derivatives, or aminostyrene derivatives.
In a preferred embodiment of the present invention, one or two host material compounds are contained in the light-emitting layer.
In a preferred embodiment of the present invention, two host material compounds are contained in the light-emitting layer, and the two host material compounds form an exciplex.
In a preferred embodiment of the present invention, the host material of the light emitting region used is selected from one or more of the following compounds BH1-BH 6:
in the present invention, the light emitting region may include a phosphorescent or fluorescent guest material to improve the fluorescent or phosphorescent characteristics of the organic electroluminescent device. The guest material may use those conventionally used in the art according to the present invention. Preferably, specific examples of the phosphorescent guest material include metal complexes of iridium, platinum, and the like. For example, Ir (ppy)3[ fac-tris (2-phenylpyridine) iridium]And the like, blue phosphorescent materials such as FIrpic and FIr6, and red phosphorescent materials such as Btp2Ir (acac). In a preferred embodiment of the present invention, the guest materials of the light-emitting layer used are those suitable for co-formulation with blue light-emitting materials, preferably selected from one of the following compounds BD1 to BD 13:
in the light emitting region of the present invention, the ratio of the host material to the guest material is used in a range of 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 by mass.
In the light emitting region of the present invention, a host material may also be mixed with a small amount of a dopant to produce a material that emits light, which may be an organic compound or a metal complex such as Al that emits fluorescence by singlet excitation; or a material such as a metal complex that emits light by multiple-state excitation into a triplet state or more. The dopant may be, for example, an inorganic compound, an organic compound, or an organic/inorganic compound, and one or more species thereof may be used.
The thickness of the light emitting region of the present invention may be 10 to 50nm, preferably 15 to 30nm, 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 provided between the anode and the light emitting region, and includes a hole injection layer and a hole transport layer, preferably a hole injection layer, a first hole transport layer, and a second hole transport layer. According to the present invention, the diamine derivative of the present invention is used for the hole transporting region.
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 that can sufficiently accept 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 layer of a host organic material and a P-type dopant material. In order to smoothly inject holes from the anode into the organic film layer, the HOMO level of the host organic material must have a certain characteristic with the P-type dopant material, so that the generation of a charge transfer state between the host material and the dopant material is expected, and ohmic contact between the hole injection layer and the anode is realized, thereby realizing efficient injection of holes from the electrode to the hole injection layer. 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 doping material is less than or equal to 0.5 eV. Therefore, for hole-type host materials with different HOMO levels, different P-type doping materials need to be selected to match with the hole-type host materials, so that ohmic contact of an interface can be realized, and the hole injection effect is improved.
Preferably, the hole injecting host organic material comprises or consists of one or more of the diamine derivatives of the present invention as described previously. Preferably, the hole injection layer is composed of the diamine derivative of the present invention and other doping materials conventionally used for the hole injection layer.
Preferably, the P-type doping 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-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or a cyclopropane derivative, such as 4,4',4 "- ((1E,1' E, 1" E) -cyclopropane-1, 2, 3-trimethylenetri (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 present invention, the P-type doping material used is selected from any one of the following compounds HI-1 to HI-10:
in one embodiment of the invention, the ratio of host organic material to P-type dopant material used is in the range of 99:1 to 95:5, preferably 99:1 to 97:3, by mass.
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, the hole transport layer may be disposed on the hole injection layer. Preferably, 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: aromatic amine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like, but are not limited thereto.
In a preferred embodiment, the hole transport layer is located between the hole injection layer and the light emitting layer; the first hole transport layer is located between the hole injection layer and the second hole transport layer, and the second hole transport layer is located between the first hole transport layer and the light emitting layer. In one embodiment of the invention, the hole transport layer comprises the same diamine derivative of the invention as the hole injection layer host organic material. In a preferred embodiment, the first hole transport layer material is the same as the hole injection layer host organic material and is a diamine derivative of the present invention. In a more preferred embodiment, the first hole transport layer comprises or consists of one or more of the diamine derivatives 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 is composed of a carbazole-based aromatic amine derivative. Preferably, the compound of the second hole transport layer may be
In yet another 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 one or more of the diamine derivatives of the present invention. In another embodiment, the first hole transport layer material and the hole injection layer host organic material are the same, both diamine derivatives of the present invention, and are a single diamine derivative, and the second hole transport layer comprises or consists of a diamine derivative of the present invention.
The thickness of the hole transport layer of the present invention (the sum of the thicknesses of the first hole transport layer and the second hole transport layer) may be 80 to 200nm, preferably 100-150nm, but the thickness is not limited to this range. Preferably, the thickness of the first hole transport layer may be 100-150nm, preferably 115-125 nm; the thickness of the second hole transport layer is 5 to 50nm, preferably 5 to 20nm, more preferably 5 to 10 nm.
The invention does not deny the substrate collocation principle of the traditional hole materials, but further superposes the physical parameters screened by the traditional materials, namely, the influence effects of HOMO energy level, carrier mobility, film phase stability, heat resistance stability of the materials and the like on the hole injection efficiency of the organic electroluminescent device are acknowledged. On the basis, the material screening conditions are further increased, and the material selection accuracy for preparing the high-performance organic electroluminescent device is improved by selecting more excellent organic electroluminescent materials for matching the device.
Electron transport region
In the organic electroluminescent device of the present invention, the 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 conventionally used in the art, 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. Heterocyclic nitrogen-based materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electricity for organic electroluminescent devices known in the art can be usedMaterials for the transport layer, e.g. in Alq3And metal complexes of hydroxyquinoline derivatives represented by 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 number: 1459162-51-6), 2- (4- (9, 10-di (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 LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, and the like. Alq3And the LiQ structural formula is as follows:
in a preferred organic electroluminescent device of the invention, the electron transport layer comprises or consists of a nitrogen heterocyclic derivative of the general formula (a):
wherein
Ar1、Ar2And Ar3Represent, independently of one another: substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms5-C30Heterocyclyl, said heteroatoms being independently from each other selected from N, O or S; preferably phenyl, pyridyl, carbazolyl, dimethylfluorenyl, biphenyl, dibenzofuranyl, triphenylenyl, phenanthrenyl, naphthyl, 1-phenylbenzimidazol-2-yl, isoquinolinyl,
L represents a single bond, substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted, containing one or more hetero atomsC of an atom5-C30(ii) heterocyclylene, each of said heteroatoms being independently selected from N, O or S; preferably a single bond, phenylene, biphenylene, phenylenephenylene pyridyl;
n represents 1 or 2, preferably 1;
X1、X2、X3independently of one another, N or CH, with the proviso that X1、X2、X3At least one group in (a) represents N.
In a preferred embodiment of the present invention, the electron transport layer comprises any one of the compounds selected from the group consisting of:
in a more preferred embodiment of the present invention, the electron transport layer comprises any one of the compounds selected from the group consisting of: (E2) (E5), (E12), (E16) or (E23).
In a preferred embodiment of the present invention, the electron transport layer comprises, in addition to the compound of the formula (A), other compounds conventionally used in electron transport layers, for example, Alq3LiQ is preferred. In a more preferred embodiment of the present invention, the electron transport layer is composed of one of the compounds of the general formula (a) and one of the other compounds conventionally used for electron transport layers, preferably LiQ.
The hole injection and transport rates of the hole transport region containing the diamine derivative of the present invention can be well matched with the electron injection and transport rates. Preferably, the hole injection and transport rate of the hole transport region containing the diamine derivative of the present invention can be better matched with the electron injection and transport rate of the electron transport region containing the nitrogen heterocycle derivative of the general formula (a).
Therefore, in a particular embodiment of the present invention, the use of an electron transport region comprising or consisting of one or more nitrogen heterocyclic derivatives of the general formula (a) in combination with a hole transport region comprising a diamine derivative of the present invention achieves a relatively better technical result. In a particularly preferred embodiment of the present invention, the use of an electron transport region comprising or consisting of one or more nitrogen heterocyclic derivatives of the general formula (a) in combination with a hole injection layer using a single diamine derivative of the present invention as a host material and a first hole transport layer comprising the same single diamine derivative of the present invention achieves a further advantageous technical effect.
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 extraction efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be added on the electrode on the light extraction side of the device. According to the principle of optical absorption and refraction, the CPL cover layer material should have a higher refractive index as well as a better refractive index, and the absorption coefficient should be smaller as well. 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 capping layer is typically 5-300nm, preferably 20-100nm and more preferably 40-80nm thick.
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 layers of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer. The present invention also relates to a method of preparing an organic electroluminescent device comprising sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film 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, LITI, or the like may be used, but are not limited thereto. In the present invention, it is preferable that the respective layers are formed by a vacuum evaporation method. The individual process conditions in the vacuum evaporation process can be routinely selected by the person skilled in the art according to the actual requirements.
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, may be used as a single layer by forming a film in admixture with another material, or may be used as a laminated structure of layers formed alone, layers formed in admixture with each other, or a laminated structure of layers formed alone and layers formed in admixture with each other.
The invention also 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 invention. 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.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
Examples
Unless otherwise indicated, 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.
I. Preparation of the Compounds of the invention
Example 1: compound H2
In a three-necked flask, 0.012mol of raw material A, 0.01mol of raw material B, 0.02mol of sodium carbonate and a mixed solvent (150ml of toluene and 45ml of H) are added under the protection of nitrogen2O), stirring and mixing, then adding 1X 10-4mol tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) Heating ofThe reaction was refluxed to 105 ℃ for 24 hours, and a sample was taken from the plate to indicate that no starting material B remained and the reaction was complete. Then, the mixture was naturally cooled to room temperature, filtered, and the filtrate was subjected to rotary evaporation under reduced pressure (-0.09MPa, 85 ℃ C.) to obtain an intermediate M through a neutral silica gel column (silica gel 100-200 mesh; eluent: dichloromethane: petroleum ether: 2:3 (volume ratio)). Elemental analysis Structure (molecular formula C)34H24ClN): test values: c, 84.69; h, 5.08; cl, 7.28; and N, 2.90. LC-MS: found 482.35([ M + H)]+) (ii) a Theoretical values are as follows: 481.16.
in a three-necked flask, 0.012mol of raw material C, 0.01mol of intermediate M, 0.02mol of sodium carbonate and a mixed solvent (150ml of toluene and 45ml of H) were added under the protection of nitrogen gas2O), stirring and mixing, then adding 1X 10-4mol tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) The reaction was heated to 105 ℃ and refluxed for 24 hours, and a sample was taken from the plate to show that no intermediate M remained and the reaction was complete. Naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (-0.09MPa, 85 ℃), passing through a neutral silica gel column (silica gel 100 meshes and 200 meshes, eluent: dichloromethane: petroleum ether: 3:4 (volume ratio)), and obtaining the target compound. Elemental analysis Structure (molecular formula C)58H42N2): test values are: c90.92; h5.45; and (3) N3.71. LC-MS: found 767.14([ M + H ]]+) (ii) a Theoretical value: 766.33.
example 2: compound H98
In a three-necked flask, 0.012mol of raw material A, 0.01mol of raw material B, 0.02mol of sodium carbonate and a mixed solvent (150ml of toluene and 45ml of H) are added under the protection of nitrogen2O), stirring and mixing, then adding 1X 10-4mol tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) The reaction was heated to 105 ℃ and refluxed for 24 hours, and the reaction was completed when no raw material B remained as a sample on the plate. Then, the mixture is naturally cooled to room temperature, filtered, and the filtrate is subjected to reduced pressure rotary evaporation (-0.09MPa, 85 ℃) and then is filtered through a neutral silica gel column (silica gel 100 meshes and 200 meshes, eluent: dichloromethane: petroleum ether: 3:5(Volume ratio)) to yield intermediate M. Elemental analysis Structure (molecular formula C)22H14Cl2): test values are: c, 75.57; h, 4.10; cl, 20.35. LC-MS: found 349.17([ M + H)]+) (ii) a Theoretical value: 348.05.
a500 ml three-necked flask was charged with 0.024mol of the raw material C, 0.01mol of the intermediate M, 0.03mol of potassium tert-butoxide, and 1X 10 mol of the intermediate M in a nitrogen-purged atmosphere-4mol tris (dibenzylideneacetone) dipalladium (Pd)2(dba)3)、1×10-4mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, and a sample of the plaque showed no intermediate M remaining. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column (silica gel 100-200 meshes, eluent: dichloromethane: petroleum ether is 3:7 (volume ratio)) to obtain the target compound. Elemental analysis Structure (molecular formula C)58H42N2): test values are: c, 90.75; h, 5.61; and N, 3.59. LC-MS: found 767.31([ M + H)]+) (ii) a Theoretical value: 766.33.
example 3: compound H114
In a three-necked flask, 0.01mol of raw material A, 0.022mol of raw material B, 0.02mol of sodium carbonate and a mixed solvent (150ml of toluene and 45ml of H) are added under the protection of nitrogen2O), stirring and mixing, then adding 1X 10-4mol tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) The reaction was heated to 105 ℃ and refluxed for 24 hours, and the reaction was completed when no raw material A remained as a sample on the plate. Then, the mixture was naturally cooled to room temperature, filtered, and the filtrate was subjected to rotary evaporation under reduced pressure (-0.09MPa, 85 ℃ C.) to obtain an intermediate M through a neutral silica gel column (silica gel 100-200 mesh; eluent: dichloromethane: petroleum ether: 3:5 (volume ratio)). Elemental analysis Structure (molecular formula C)18H10Br2O2): test values are: c, 51.79; h, 2.37; br, 38.17. LC-MS: found 416.83([ M + H)]+) (ii) a Theoretical value: 415.90.
500ml three-mouth bottle, under the atmosphere of nitrogen gas, adding 0.024mol of raw materialMaterial C, 0.01mol of intermediate M, 0.03mol of potassium tert-butoxide, 1X 10-4mol tris (dibenzylideneacetone) dipalladium (Pd)2(dba)3)、1×10-4mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, and a sample of the dot plate showed no intermediate M remaining. Naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column (silica gel 100-200 meshes, eluent: dichloromethane: petroleum ether: 3:7 (volume ratio)) to obtain the target compound. Elemental analysis Structure (molecular formula C)54H38N2O2): test values are: c, 86.74; h, 5.21; and N, 3.69. LC-MS: found 747.35([ M + H)]+) (ii) a Theoretical value: 746.29.
example 4: compound H130
In a three-necked flask, 0.012mol of raw material A, 0.01mol of raw material B, 0.02mol of sodium carbonate and a mixed solvent (150ml of toluene and 45ml of H) are added under the protection of nitrogen2O), stirring and mixing, then adding 1X 10-4mol tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) The reaction was heated to 105 ℃ and refluxed for 24 hours, and the reaction was completed when no material B remained as a sample on the plate. Then, the mixture was naturally cooled to room temperature, filtered, and the filtrate was subjected to rotary evaporation under reduced pressure (-0.09MPa, 85 ℃ C.) to obtain an intermediate M through a neutral silica gel column (silica gel 100-200 mesh; eluent: dichloromethane: petroleum ether: 2:3 (volume ratio)). Elemental analysis Structure (molecular formula C)34H24ClN): test values are: c, 84.67; h, 5.11; cl, 7.31; and N, 2.96. LC-MS: found 482.23([ M + H)]+) (ii) a Theoretical values are as follows: 481.16.
in a three-necked flask, 0.012mol of raw material C, 0.01mol of intermediate M, 0.02mol of sodium carbonate and a mixed solvent (150ml of toluene and 45ml of H) were added under the protection of nitrogen gas2O), stirring and mixing, then adding 1X 10-4mol tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) The reaction was heated to 105 ℃ and refluxed for 24 hours, and a sample was taken from the plate to show that no intermediate M remained and the reaction was complete. Naturally cooling to room temperature, filteringThe filtrate was subjected to rotary evaporation under reduced pressure (-0.09MPa, 85 ℃ C.), and passed through a neutral silica gel column (silica gel 100-200 mesh, eluent: dichloromethane: petroleum ether 3:4 (volume ratio)), to obtain the objective compound. Elemental analysis Structure (molecular formula C)52H36N2): test values are: c90.77; h5.21; and (4) N4.03. LC-MS: found 689.34([ M + H ]]+) (ii) a Theoretical value: 688.29.
the following compounds were prepared in a similar manner to example 1, starting with the synthesis shown in table 1 below. The nuclear magnetic hydrogen spectrum of the compound H1 is shown in figure 3.
TABLE 1
Compound testing
1. Measurement of glass transition temperature Tg, Eg level, hole mobility, and triplet level T1
Glass transition temperature Tg: measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter, Nachi company, Germany), the rate of temperature rise was 10 ℃/min.
HOMO energy level: the test was conducted in a vacuum environment by an ionization energy test system (IPS 3).
Eg energy level: based on the tangent line of the ultraviolet spectrophotometry (UV absorption) baseline of the single film of the material and the ascending side of the first absorption peak, the intersection value of the tangent line and the baseline is calculated.
Hole mobility: the material was fabricated into a single charge device and measured by space charge (induced) limited current method (SCLC).
Triplet energy level T1: the material was dissolved in toluene solution and tested by Hitachi F4600 fluorescence spectrometer.
The results of the physical property tests are shown in Table 2. The structural formula HT1-HT6 is shown below.
TABLE 2
As can be seen from the data in Table 2, the glass transition temperatures Tg of the compounds of the invention tested are, for example, in the range of 120-160 ℃ and preferably in the range of 120-140 ℃ and both exceed 120 ℃; the HOMO energy level is within the range of 5.45-5.65eV, preferably 5.50-5.57eV, and the HOMO energy levels of the compounds are relatively close; the Eg level is, for example, in the range of 3.0-3.3eV, preferably 3.05-3.25 eV; hole mobility is 5.3-9.0cm2V.s, preferably 5.35-9.57cm2V · s range; t1 is, for example, in the range 2.25-2.6eV, preferably 2.30-2.5 eV. In addition, the Tg of the compounds of the invention relative to the comparative compounds is on average higher and the HOMO level comparable to that of the comparative compounds HT1-HT 6. "- -" represents no detection.
From the above, the compound of the present invention has a suitable HOMO level, a higher glass transition temperature Tg, a higher hole mobility and a wider band gap (Eg), and is suitable for use as a hole transport material in an organic electroluminescent device, so that the organic electroluminescent device has high efficiency, low voltage and long lifetime.
2. Stability of film phase
To better illustrate the stability of the phase state of the films of the compounds of the present invention, the compounds of the present application, H1, H20, H136, H257, and the comparative structures HT3-HT6 (see structural formula below) were subjected to film crystallization acceleration tests: the method comprises the following steps of evaporating 80nm single films on alkali-free glass respectively by adopting a vacuum evaporation mode, packaging in a glove box (the water oxygen content is less than 0.1ppm), respectively placing packaged samples under the conditions of 80 ℃ and 115 ℃, and regularly observing the state of the single films by using a microscope (LEICA, DM8000M, 5 x 10 multiplying power), wherein the experimental results are shown in a table 2-1, and the surface morphology of the material is shown in a figure 2:
TABLE 2-1
| Name of Material | Crystallization time at 80 ℃ | Crystallization time at 115 |
| H1 | ||
| 1000h of non-crystallization | Does not crystallize in 200h | |
| H20 | 1000h of non-crystallization | Does not crystallize in |
| H136 | ||
| 1000h of non-crystallization | Does not crystallize in | |
| H257 | ||
| 1000h of non-crystallization | Does not crystallize in 200h | |
| HT3 | Crystallization occurred within 456h | Crystallization occurs within 120h |
| HT4 | Crystals appeared after 432h | Crystallization occurred for 72h |
| HT5 | Crystallization occurred in 480h | Crystallization occurred within 96h |
| HT6 | Crystallization occurred within 600h | Crystallization occurred within 144h |
As can be seen from Table 2-1, the compound of the present invention did not crystallize at 80 ℃ for 1000 hours and did not crystallize at 115 ℃ for 200 hours, whereas the comparative compound crystallized at 80 ℃ for 600 hours and at 115 ℃ for 144 hours. This indicates that the membrane phase stability of the compounds of the invention is far superior to the compounds known in the prior art.
Furthermore, it is noteworthy that, for example, although the compound of the invention H1 differs from the comparative compound HT3-HT6 only in the position of the attachment to the naphthyl group, unexpectedly, the membrane phase stability of the compound of the invention H1 is much higher than that of the comparative compound, which was not expected from the known compounds.
The excellent film phase stability enables the device structure applying the compound of the present application to have excellent stability in a high temperature environment, which is expressed by longer life, especially high temperature life.
Preparation of organic electroluminescent device
The molecular structural formula of the materials involved in the following preparation is as follows:
the compound prepared in I is used below to demonstrate the effects of the present invention by taking a top emission organic electroluminescent device (blue light device) as an example, but the present application is not limited thereto.
Comparative example 1
The organic electroluminescent device was prepared as follows:
a) using transparent glass as a substrate, washing an anode layer (Ag (150nm)) on the substrate, respectively ultrasonically cleaning the anode layer with deionized water, acetone and ethanol for 15 minutes, and then treating the anode layer in a plasma cleaner for 2 minutes;
b) on the anode layer washed, a hole transport material HT1 and a P-type dopant material HI-1 were placed in two evaporation sources under a vacuum of 1.0E-5The vapor deposition rate of a compound HT1 under Pa pressure is controlled to be
Controlling the evaporation rate of the P-type doping material HI-1 to be
Co-evaporating to form a hole injection layer with the thickness of 10 nm;
c) evaporating a first hole transport layer on the hole injection layer in a vacuum evaporation mode, wherein the hole transport layer is made of a compound HT1 and has the thickness of 120 nm;
d) evaporating a second hole transport layer B-1 on the first hole transport layer in a vacuum evaporation mode, wherein the thickness of the second hole transport layer B-1 is 10 nm;
e) evaporating a luminescent layer material on the second hole transport layer in a vacuum evaporation mode, wherein the host material is BH1, the guest material is BD1, the mass ratio is 97:3, and the thickness is 20 nm;
f) on the light-emitting layer, ET1 and LiQ were evaporated by vacuum evaporation, ET1: the LiQ mass ratio is 50:50, the thickness is 30nm, and the layer is used as an electron transport layer;
g) evaporating LiF on the electron transport layer in a vacuum evaporation mode, wherein the thickness of the LiF is 1nm, and the LiF is an electron injection layer;
h) vacuum evaporating an Mg: Ag (1:9) electrode layer with the thickness of 16nm on the electron injection layer, wherein the layer is a cathode layer;
i) CPL material CPL-1 is evaporated in vacuum on the cathode layer, and the thickness is 70 nm.
Comparative examples 2 to 12
The organic materials in steps b), c), d), E), f) were replaced with the organic materials shown in table 3, respectively, according to the method of device preparation example 1, wherein the proportions of ET1: LiQ, E2: LiQ, E5: LiQ, E12: LiQ, E16: LiQ, E23: LiQ were all 50: 50.
Examples 1 to 106
The procedure of device preparation example 1 was followed, except that the organic materials in steps b), c), d), E), f) were replaced with the organic materials shown in table 3, respectively, wherein the proportions of ET1: LiQ, E2: LiQ, E5: LiQ, E12: LiQ, E16: LiQ, E23: LiQ were all 50: 50.
TABLE 3
After the OLED light-emitting device was prepared as described above, the cathode and the anode were connected by a known driving circuit, and various properties of the device were measured. The device measurement performance results of examples 1 to 104 and comparative examples 1 to 12 are shown in table 4.
TABLE 4
Note: LT95 refers to the time it takes for the device luminance to decay to 95% of the original luminance at a luminance of 1500 nits;
voltage, current efficiency and color coordinates were tested using the IVL (current-voltage-brightness) test system (frastd scientific instruments, su); the current density is 10mA/cm2。
The life test system is an EAS-62C type OLED life test system of Japan scientific research Co.
The high-temperature service life means that the brightness of the device is 10mA/cm at the temperature of 80 DEG C2In this case, the time taken for the luminance of the device to decay to 80% of the original luminance.
As can be seen from the results of table 4, for the blue device, the organic electroluminescent device (hereinafter referred to as inventive device) prepared using the diamine derivative of the present invention as the organic host material for the hole injection layer and simultaneously as the hole transport layer material, has significantly improved current efficiency and significantly increased high-temperature lifetime LT95 while lowering the voltage, as compared to the organic electroluminescent device (hereinafter referred to as comparative device) prepared using other compounds having a structure similar to that of the compound of the present invention as the host material for the hole injection layer and simultaneously as the hole transport layer material. It can be seen that, although the compounds of the invention are very similar in structure to the comparative compounds, the devices of the invention unexpectedly achieve better voltage, current efficiency, LT95 and high temperature lifetime than the comparative devices, which would not be expected by the person skilled in the art from the prior art.
For other optical devices, similar significantly better effects can be obtained by using the diamine derivative of the present invention in the hole transport region.
Furthermore, in the inventive examples, the devices obtained with the electron transport layer compounds E2, E5, E12, E16, E23 (examples 26-84/94-106) achieved an average lower voltage, an average higher current efficiency, an average longer high temperature lifetime and a comparable LT95 lifetime compared to the devices obtained with the electron transport layer compound ET1 (examples 1-25, 85-93).
After the diamine derivative is substituted by tert-butyl, the mobility of the material is improved, so that an organic electroluminescent device using the diamine derivative as a hole transport layer material has longer LT95 and high-temperature service life.
Claims (10)
1. A diamine derivative having the following general formula (1):
wherein
A represents a structure represented by general formula (2) to general formula (8);
L1represented by a direct bond, phenylene, furanylene, naphthylene or biphenylene;
L2represented by a direct bond, phenylene, furanylene, naphthylene or biphenylene;
and when A is represented by the general formula (2) or the general formula (3), L1And L2Not being a direct bond at the same time;
represents L1And R1Can be connected with each other to form a ring, or can be disconnected with each other; when L is1And R1When interconnected to form a ring, L1、R1And N together form substituted or unsubstitutedCarbazolyl group of (a);
R1to R4Independently represent hydrogen, substituted or unsubstituted aryl with 6-30 ring carbon atoms, substituted or unsubstituted 5-30 membered heteroaryl, wherein the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom, and when A represents the structure shown in the general formula (2) or the general formula (3), R represents1To R4Not simultaneously represented as phenyl;
said substituents being optionally selected from deuterium atoms, C1-C6Alkyl, phenyl, naphthyl, biphenyl, carbazolyl, N-phenylcarbazolyl, adamantyl, thienyl, phenylthienyl, furyl, phenylfuryl, benzofuryl or dibenzofuryl; preferably, C1-C6Alkyl is methyl, ethyl, propyl, isopropyl and/or tert-butyl.
2. Diamine derivative according to claim 1, wherein
R1To R4Each independently represents hydrogen or a substituted or unsubstituted group: phenyl, biphenyl, naphthyl, phenanthryl, pyrenyl, spirobifluorenyl, naphthylphenyl, phenylnaphthyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, and the like, furyl, benzofuryl, carbazolyl, N-phenylcarbazolyl, thienyl, benzophenanthryl, benzofuryl-phenyl, phenyl-furyl-phenyl, dibenzofuryl; preferably, when phenyl is substituted by C1-C6When substituted by alkyl, C1-C6The alkyl substituent is located para to the phenyl group.
3. Diamine derivative according to claim 1 or 2, wherein
A represents a structure represented by general formula (2) or (3);
L1、L2each independently represents a direct bond, phenylene, biphenylene or furanylene, and L1、L2Not being a direct bond at the same time; or L2Represented by a direct bond, phenylene or furanylene, L1、R1Together with N to form a substituted or unsubstituted carbazolyl groupN-phenylcarbazolyl is preferred.
4. The diamine derivative according to claim 1 or 2, wherein A represents a structure represented by general formulae (4) to (8);
L1、L2each independently represents a direct bond, phenylene or furanylene; or L2Represented by a direct bond, phenylene or furanylene, L1、R1And N together form a substituted or unsubstituted carbazolyl group, preferably an N-phenylcarbazolyl group.
5. Diamine derivative according to claim 1 or 2, having a structure of general formula (1-1):
wherein
A、L2、R2To R4As defined in claim 1 or 2; preferably, in the formula (1-1), R2Is hydrogen or phenyl.
6. The aromatic amine-based compound according to any one of claims 1 to 5, which is selected from the group consisting of the following compounds;
7. an organic electroluminescent device comprising an anode, a hole transport region, a light emitting region, an electron transport region and a cathode in this order, wherein the hole transport region comprises the diamine derivative of any one of claims 1 to 6; preferably, the hole transport region comprises 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 the diamine derivative of any one of claims 1 to 6; more preferably, the first hole transport layer is composed of the diamine derivative according to any one of claims 1 to 6, and the hole injection layer is composed of the diamine derivative according to any one of claims 1 to 6 and other doping materials conventionally used for hole injection layers.
8. The organic electroluminescent device according to claim 7, wherein the electron transport region comprises a nitrogen heterocyclic compound represented by the following general formula (A):
wherein
Ar1、Ar2And Ar3Independently of one another, represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms5-C30Heterocyclyl, said heteroatoms being independently from each other selected from N, O or S; l represents a single bond, substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted C containing one or more hetero atoms5-C30(ii) heterocyclylene, each of said heteroatoms being independently selected from N, O or S;
n represents 1 or 2, preferably 1;
X1、X2、X3independently of one another, N or CH, with the proviso that X1、X2、X3At least one group in (a) represents N.
9. Use of a diamine derivative as defined in any one of claims 1 to 6 as a hole transport material in an organic electroluminescent device.
10. A display device comprising the organic electroluminescent device according to any one of claims 7 to 8.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2020112985828 | 2020-11-18 | ||
| CN202011298582 | 2020-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114516804A true CN114516804A (en) | 2022-05-20 |
Family
ID=81594667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110121432.8A Pending CN114516804A (en) | 2020-11-18 | 2021-01-28 | Diamine derivative and organic electroluminescent device using same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114516804A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114716329A (en) * | 2022-04-01 | 2022-07-08 | 上海钥熠电子科技有限公司 | Organic compound and organic photoelectric device |
| CN115073306A (en) * | 2022-07-14 | 2022-09-20 | 北京八亿时空液晶科技股份有限公司 | Acenaphthene derivative and organic electroluminescent element containing same |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101668730A (en) * | 2007-04-26 | 2010-03-10 | Lg化学株式会社 | New diamine derivatives and organic electronic device using the same |
| CN105061371A (en) * | 2008-11-25 | 2015-11-18 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element |
| WO2019027040A1 (en) * | 2017-08-03 | 2019-02-07 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
| CN109467543A (en) * | 2018-11-12 | 2019-03-15 | 长春海谱润斯科技有限公司 | A kind of triarylamine derivative and its organic electroluminescence device |
| WO2020103724A1 (en) * | 2018-11-20 | 2020-05-28 | 江苏三月光电科技有限公司 | Organic electroluminescent device, method for preparing same, and a display apparatus comprising same |
| CN111909043A (en) * | 2020-07-09 | 2020-11-10 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, electronic component, and electronic device |
-
2021
- 2021-01-28 CN CN202110121432.8A patent/CN114516804A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101668730A (en) * | 2007-04-26 | 2010-03-10 | Lg化学株式会社 | New diamine derivatives and organic electronic device using the same |
| CN105061371A (en) * | 2008-11-25 | 2015-11-18 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element |
| WO2019027040A1 (en) * | 2017-08-03 | 2019-02-07 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
| CN109467543A (en) * | 2018-11-12 | 2019-03-15 | 长春海谱润斯科技有限公司 | A kind of triarylamine derivative and its organic electroluminescence device |
| WO2020103724A1 (en) * | 2018-11-20 | 2020-05-28 | 江苏三月光电科技有限公司 | Organic electroluminescent device, method for preparing same, and a display apparatus comprising same |
| CN111909043A (en) * | 2020-07-09 | 2020-11-10 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, electronic component, and electronic device |
Non-Patent Citations (1)
| Title |
|---|
| REGISTRY[ONLINE]，COLUMBUS，OHIO，US, 《STN检索报告 US REGISTRY》, pages 1 - 5 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114716329A (en) * | 2022-04-01 | 2022-07-08 | 上海钥熠电子科技有限公司 | Organic compound and organic photoelectric device |
| CN115073306A (en) * | 2022-07-14 | 2022-09-20 | 北京八亿时空液晶科技股份有限公司 | Acenaphthene derivative and organic electroluminescent element containing same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112079767B (en) | Aromatic amine compound and organic electroluminescent device comprising same | |
| CN111647009B (en) | Boron-containing compound and electronic device thereof | |
| CN111647010B (en) | Polycyclic boron-containing compound and electronic device thereof | |
| CN111263753B (en) | Compound and organic light emitting device comprising the same | |
| CN108055841B (en) | Compound and organic electronic device comprising the same | |
| CN113402399B (en) | Arylamine organic compound and organic electroluminescent device containing same | |
| KR102245926B1 (en) | Organic light emitting device | |
| CN114315693A (en) | Arylamine compound and organic electroluminescent device comprising same | |
| CN113999256A (en) | Boron-containing organic compound and light-emitting device | |
| KR101628438B1 (en) | NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AND ORGANIC ElECTRONIC DEVICE COMPRISING THE SAME | |
| CN114516804A (en) | Diamine derivative and organic electroluminescent device using same | |
| CN114478265A (en) | Arylamine compound and application thereof in organic electroluminescent device | |
| CN114315694A (en) | Arylamine compound and organic electroluminescent device prepared from same | |
| CN114075115A (en) | Amine compound and organic electroluminescent device containing same | |
| CN114075116A (en) | Spirofluorene compound and organic electroluminescent device containing same | |
| CN114075114A (en) | Homogeneous benzene arylamine compound and organic electroluminescent device comprising same | |
| CN114989022A (en) | Compound containing triarylamine and phenanthrene structure and application thereof | |
| CN114075113A (en) | Double aromatic amine compound and organic electroluminescent device containing same | |
| CN115403586A (en) | Triazine-containing compound and organic electroluminescent device comprising same | |
| CN114068825B (en) | Organic electroluminescent device and display device having multi-hole transport channel material | |
| CN114315692B (en) | Aromatic amine compound and organic electroluminescent device comprising same | |
| CN114068824B (en) | Organic electroluminescent device with multi-hole transmission channel material | |
| CN116217409B (en) | Aromatic amine compound and organic electroluminescent device prepared from same | |
| CN115028539A (en) | Arylamine derivative and organic electroluminescent device using same | |
| CN116217463B (en) | Aromatic amine organic compound and organic electroluminescent device prepared from same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |