WO2022138950A1 - Élément électroluminescent organique et dispositif électronique - Google Patents
Élément électroluminescent organique et dispositif électronique Download PDFInfo
- Publication number
- WO2022138950A1 WO2022138950A1 PCT/JP2021/048350 JP2021048350W WO2022138950A1 WO 2022138950 A1 WO2022138950 A1 WO 2022138950A1 JP 2021048350 W JP2021048350 W JP 2021048350W WO 2022138950 A1 WO2022138950 A1 WO 2022138950A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- group
- carbon atoms
- ring
- Prior art date
Links
- 239000010410 layer Substances 0.000 claims abstract description 643
- 239000012044 organic layer Substances 0.000 claims abstract description 520
- 239000000463 material Substances 0.000 claims abstract description 340
- 239000011368 organic material Substances 0.000 claims abstract description 128
- 239000000470 constituent Substances 0.000 claims abstract description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 875
- 150000001875 compounds Chemical class 0.000 claims description 818
- 125000000623 heterocyclic group Chemical group 0.000 claims description 341
- 125000004429 atom Chemical group 0.000 claims description 280
- 125000003118 aryl group Chemical group 0.000 claims description 266
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 242
- 125000000217 alkyl group Chemical group 0.000 claims description 241
- 125000001424 substituent group Chemical group 0.000 claims description 234
- -1 diamine compound Chemical class 0.000 claims description 225
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 146
- 230000005525 hole transport Effects 0.000 claims description 142
- 125000003342 alkenyl group Chemical group 0.000 claims description 93
- 125000000304 alkynyl group Chemical group 0.000 claims description 89
- 229910052799 carbon Inorganic materials 0.000 claims description 74
- 125000003277 amino group Chemical group 0.000 claims description 69
- 238000005401 electroluminescence Methods 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
- 125000000732 arylene group Chemical group 0.000 claims description 63
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- 125000002950 monocyclic group Chemical group 0.000 claims description 48
- 125000001188 haloalkyl group Chemical group 0.000 claims description 45
- 150000001721 carbon Chemical group 0.000 claims description 42
- 125000005647 linker group Chemical group 0.000 claims description 41
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 35
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000004434 sulfur atom Chemical group 0.000 claims description 33
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 150000001555 benzenes Chemical group 0.000 claims description 13
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
- 125000002521 alkyl halide group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- 150000005041 phenanthrolines Chemical class 0.000 claims description 3
- 101100410784 Arabidopsis thaliana PXG3 gene Proteins 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 239000010408 film Substances 0.000 description 105
- 230000032258 transport Effects 0.000 description 94
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 51
- 238000000034 method Methods 0.000 description 48
- 239000000758 substrate Substances 0.000 description 45
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 37
- 238000002347 injection Methods 0.000 description 35
- 239000007924 injection Substances 0.000 description 35
- 230000004888 barrier function Effects 0.000 description 28
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 28
- 125000001624 naphthyl group Chemical group 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 22
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 21
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 21
- 238000005259 measurement Methods 0.000 description 21
- 150000001975 deuterium Chemical group 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000001228 spectrum Methods 0.000 description 17
- 239000011521 glass Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 14
- 238000007740 vapor deposition Methods 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 13
- 125000000547 substituted alkyl group Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 230000007423 decrease Effects 0.000 description 12
- 239000000594 mannitol Substances 0.000 description 12
- 238000007363 ring formation reaction Methods 0.000 description 12
- 125000005017 substituted alkenyl group Chemical group 0.000 description 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 11
- 235000010290 biphenyl Nutrition 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 11
- 238000004364 calculation method Methods 0.000 description 11
- 238000000295 emission spectrum Methods 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000003107 substituted aryl group Chemical group 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 125000005577 anthracene group Chemical group 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 9
- 229910045601 alloy Inorganic materials 0.000 description 9
- 239000000956 alloy Substances 0.000 description 9
- 150000004696 coordination complex Chemical class 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 description 9
- 230000003595 spectral effect Effects 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 125000002619 bicyclic group Chemical group 0.000 description 8
- 125000001725 pyrenyl group Chemical group 0.000 description 8
- 230000006798 recombination Effects 0.000 description 8
- 238000005215 recombination Methods 0.000 description 8
- 230000000630 rising effect Effects 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 7
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 150000001556 benzimidazoles Chemical class 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 238000004544 sputter deposition Methods 0.000 description 7
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001296 phosphorescence spectrum Methods 0.000 description 6
- 239000010453 quartz Substances 0.000 description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 150000002910 rare earth metals Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 239000004396 Octenyl succinic acid modified gum arabic Substances 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- WINTXHPCODMMRI-UHFFFAOYSA-N benzene naphthalene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 WINTXHPCODMMRI-UHFFFAOYSA-N 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 150000001716 carbazoles Chemical group 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 230000005283 ground state Effects 0.000 description 4
- 239000000665 guar gum Substances 0.000 description 4
- 229910003437 indium oxide Inorganic materials 0.000 description 4
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000391 spectroscopic ellipsometry Methods 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical group C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 150000001846 chrysenes Chemical class 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002847 impedance measurement Methods 0.000 description 3
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- 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 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 150000003220 pyrenes Chemical class 0.000 description 3
- WTGQALLALWYDJH-WYHSTMEOSA-N scopolamine hydrobromide Chemical compound Br.C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 WTGQALLALWYDJH-WYHSTMEOSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 125000004426 substituted alkynyl group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 229910001930 tungsten oxide Inorganic materials 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 description 2
- 229910017073 AlLi Inorganic materials 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001454 anthracenes Chemical group 0.000 description 2
- 125000004653 anthracenylene group Chemical group 0.000 description 2
- 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 2
- 150000007860 aryl ester derivatives Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 150000001616 biphenylenes Chemical group 0.000 description 2
- KVUAALJSMIVURS-ZEDZUCNESA-L calcium folinate Chemical compound [Ca+2].C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)C=C1 KVUAALJSMIVURS-ZEDZUCNESA-L 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910021389 graphene Inorganic materials 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000005581 pyrene group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005551 pyridylene group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000010408 sweeping Methods 0.000 description 2
- 239000013077 target material Substances 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 2
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- YEBQUUKDSJCPIX-UHFFFAOYSA-N 12h-benzo[a]thioxanthene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4SC3=CC=C21 YEBQUUKDSJCPIX-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- ZBWXZZIIMVVCNZ-UHFFFAOYSA-N 4,5-dihydroacephenanthrylene Chemical compound C1=CC(CC2)=C3C2=CC2=CC=CC=C2C3=C1 ZBWXZZIIMVVCNZ-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical group C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- KMNZKANGYGKTAK-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C(=C(C=CC1)C1=NN=C(O1)C1=CC(=CC=C1)C=1OC(=NN1)C1=C(C(=CC=C1)C1=CC=CC=C1)CCCC)CCCC Chemical compound C1(=CC=CC=C1)C=1C(=C(C=CC1)C1=NN=C(O1)C1=CC(=CC=C1)C=1OC(=NN1)C1=C(C(=CC=C1)C1=CC=CC=C1)CCCC)CCCC KMNZKANGYGKTAK-UHFFFAOYSA-N 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical class COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-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
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 1
- JDPAVWAQGBGGHD-UHFFFAOYSA-N aceanthrylene Chemical group C1=CC=C2C(C=CC3=CC=C4)=C3C4=CC2=C1 JDPAVWAQGBGGHD-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000006193 alkinyl group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- CSSYLTMKCUORDA-UHFFFAOYSA-N barium(2+);oxygen(2-) Chemical class [O-2].[Ba+2] CSSYLTMKCUORDA-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical class [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating 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
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BWSNYLWZGNCWIH-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21.C1=CC=CC2=CC=CC=C21 BWSNYLWZGNCWIH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical group 0.000 description 1
- RAPRNSRXWWPZEV-UHFFFAOYSA-N spiro[fluorene-9,9'-thioxanthene] Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 RAPRNSRXWWPZEV-UHFFFAOYSA-N 0.000 description 1
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- SXXNJJQVBPWGTP-UHFFFAOYSA-K tris[(4-methylquinolin-8-yl)oxy]alumane Chemical compound [Al+3].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-].C1=CC=C2C(C)=CC=NC2=C1[O-] SXXNJJQVBPWGTP-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
Definitions
- the present invention relates to an organic electroluminescence device and an electronic device.
- Organic electroluminescence devices (hereinafter, may be referred to as "organic EL devices”) are applied to full-color displays such as mobile phones and televisions.
- organic EL devices When a voltage is applied to the organic EL element, holes are injected into the light emitting layer from the anode, and electrons are injected into the light emitting layer from the cathode. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.
- singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
- the performance of the organic EL element includes, for example, luminance, emission wavelength, chromaticity, luminous efficiency, drive voltage, and life.
- Patent Documents 1 to 6 disclose an organic EL device having a plurality of layers of hole transport bands.
- An object of the present invention is to provide an organic electroluminescence element having improved luminous efficiency and an electronic device equipped with the organic electroluminescence element.
- the present invention has a cathode, an anode, a light emitting region arranged between the cathode and the anode, and a hole transport band arranged between the anode and the light emitting region.
- the light emitting region includes at least one light emitting layer
- the at least one light emitting layer is a first light emitting layer
- the hole transport band includes a first anode-side organic layer and a second light emitting layer.
- the first anode-side organic layer includes the anode-side organic layer, and the first anode-side organic layer is in direct contact with the second anode-side organic layer, and the first anode-side organic layer and the second anode-side organic layer are in direct contact with each other. Is arranged in the order of the first anode-side organic layer and the second anode-side organic layer from the anode side between the anode and the light emitting region, and the first anode-side organic layer is the first.
- the first organic material and the second organic material contain one organic material and a second organic material, and the first organic material and the second organic material are different from each other, and the first organic material in the first anode-side organic layer is different from each other.
- the content of the material is less than 50% by mass
- the second organic material has a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a substituted or unsubstituted amino group in the molecule. It is a diamine compound having two, the second anode-side organic layer contains a second hole transport band material, and the second hole transport band material has a substituted or unsubstituted amino group as a molecule. It is a monoamine compound having one in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule, and the second hole transport zone material and the first organic material are different from each other.
- the second hole transport zone material and the second organic material are the same as or different from each other, and the first light emitting layer is a fluorescent light emitting layer and the first anode.
- the transport zone includes at least one electron transport layer
- the hole transport band includes a first anode-side organic layer and a second anode-side organic layer
- the first anode-side organic layer includes the first anode-side organic layer.
- the first anode-side organic layer and the second anode-side organic layer are in direct contact with the second anode-side organic layer, and the first anode-side organic layer and the second anode-side organic layer are said to be in direct contact with the second anode-side organic layer from the anode side between the anode and the light emitting region.
- the first anode-side organic layer and the second anode-side organic layer are arranged in this order, and the first anode-side organic layer contains a first organic material and a second organic material, and the first organic material is contained.
- the one organic material and the second organic material are different from each other, and the content of the first organic material in the first anode-side organic layer is less than 50% by mass, and the second organic material.
- the material is a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule, and the second anode-side organic layer is
- the second hole transport band material contains a second hole transport band material, and the second hole transport band material is a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a substituted or unsubstituted amino group as a molecule.
- the second hole transporting zone material and the first organic material are different from each other, and the second hole transporting zone material and the second organic material are different from each other.
- At least one electron transport layer in the electron transport band which is the same as or different from each other, contains a phenanthroline compound having a phenanthroline skeleton, and the phenantroline compound is a group represented by the following general formula (21).
- the first light emitting layer is a fluorescent light emitting layer and is contained in the first anode side organic layer.
- an organic electroluminescence element in which the refractive index NM 1 of the constituent material and the refractive index NM 2 of the constituent material contained in the second anode-side organic layer satisfy the relationship of the following mathematical formula (several NM). NM 1 > NM 2 ... (number NM)
- Each of X 21 to X 28 is a nitrogen atom, CR 21 or a carbon atom bonded to a group represented by the general formula (21), respectively. At least one of X 21 to X 28 is a carbon atom bonded to a group represented by the general formula (21).
- the plurality of groups represented by the general formula (21) are the same or different from each other.
- One or more of a set consisting of two or more adjacent R21s among a plurality of R21s Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- the R 21s that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring are independent of each other.
- Ar 2 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- p is 1, 2, 3, 4 or 5 When two or more Ar 2s are present, the two or more Ars 2 are the same as or different from each other.
- L 2 is a single bond or linking group L 2 as a linking group is Substituentally substituted or unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon groups having 1 to 50 carbon atoms, Substitutable or unsubstituted ring-forming polyvalent aromatic hydrocarbon groups having 6 to 50 carbon atoms, Substituentally substituted or unsubstituted ring forming A polyvalent heterocyclic group having 5 to 50 atoms, or two or three groups selected from the polyvalent aromatic hydrocarbon ring group and the polyvalent heterocyclic group are bonded.
- L 2 is a multi-valent multi-linking group made up of The aromatic hydrocarbon ring group and the heterocyclic group constituting L 2 as the plurality of linking groups are the same or different from each other, and adjacent groups are bonded to each other to form a ring, or each other.
- Ar 2 and L 2 as a linking group bond to each other to form a ring, or do not bond to each other.
- L 2 as a linking group and any of the carbon atoms X 21 to X 28 adjacent to the carbon atom bonded to L 2 or R 21 of CR 21 are bonded to each other to form a ring or to each other.
- * In the general formula (21) indicates the bonding position with the ring represented by the general formula (20).
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 respectively.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are present, the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are the same as or different from each other.
- the plurality of R 931s are the same as or different from each other.
- the plurality of R 932s are the same as or different from each other.
- the plurality of R 933s are the same as or different from each other.
- the plurality of R 934s are the same as or different from each other.
- the plurality of R 935s are the same as or different from each other.
- the plurality of R 936s are the same as or different from each other.
- the plurality of R 937s are present, the plurality of R 937s are the same as or different from each other.
- the present invention has a cathode, an atom, a light emitting region arranged between the cathode and the anode, and a hole transport band arranged between the anode and the light emitting region.
- the light emitting region includes at least one light emitting layer, the at least one light emitting layer is a first light emitting layer, and the first light emitting layer is a first host material and a first light emitting layer.
- the first host material containing a sex compound is a compound represented by the following general formula (H1), where the compound represented by the general formula (H1) is at least one dehydrogen.
- the hole transport zone includes a first anode-side organic layer and a second anode-side organic layer, and the first anode-side organic layer is the second anode-side organic layer.
- the first anode-side organic layer and the second anode-side organic layer are in direct contact with the layer, and the first anode-side organic layer, from the anode side, between the anode and the light emitting region.
- the second anode-side organic layer is arranged in this order, and the first anode-side organic layer contains a first organic material and a second organic material, and the first organic material and the second organic material.
- the content of the first organic material in the first anode-side organic layer is less than 50% by mass, and the second organic material is substituted or unsubstituted.
- a monoamine compound having one amino group in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule, and the second anode-side organic layer is a second hole transport zone material.
- the second hole transport zone material is a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule.
- the second hole transporting zone material and the first organic material are different from each other, and the second hole transporting zone material and the second organic material are the same as each other, or Unlike this, the first light emitting layer is a fluorescent light emitting layer, and is contained in the refractive index NM 1 of the constituent material contained in the first anode side organic layer and in the second anode side organic layer.
- the refractive index NM 2 of the constituent material satisfies the relationship of the following mathematical formula (number NM). NM 1 > NM 2 ... (number NM)
- R 301 to R 308 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Substituentally substituted or unsubstituted or unsubstitute
- L 301 and L 302 are independent of each other. Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 301 and Ar 302 are independent of each other. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are independent of each other.
- the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are the same as or different from each other.
- the plurality of R 801s are the same as or different from each other.
- the plurality of R 802s are the same as or different from each other.
- an electronic device equipped with an organic electroluminescence element according to one aspect of the present invention is provided.
- an organic electroluminescence element having improved luminous efficiency and an electronic device equipped with the organic electroluminescence element.
- hydrogen atoms include isotopes with different numbers of neutrons, namely light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
- a hydrogen atom that is, a light hydrogen atom, a heavy hydrogen atom, or a hydrogen atom is located at a bondable position in which a symbol such as "R" or "D” representing a deuterium atom is not specified in the chemical structural formula. It is assumed that the triple hydrogen atom is bonded.
- the number of carbon atoms forming a ring constitutes the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound). Represents the number of carbon atoms among the atoms to be used. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of carbons forming the ring.
- the "ring-forming carbon number” described below shall be the same unless otherwise stated.
- the benzene ring has 6 ring-forming carbon atoms
- the naphthalene ring has 10 ring-forming carbon atoms
- the pyridine ring has 5 ring-forming carbon atoms
- the furan ring has 4 ring-forming carbon atoms.
- the ring-forming carbon number of the 9,9-diphenylfluorenyl group is 13
- the ring-forming carbon number of the 9,9'-spirobifluorenyl group is 25.
- the carbon number of the alkyl group is not included in the ring-forming carbon number of the benzene ring.
- the ring-forming carbon number of the benzene ring substituted with the alkyl group is 6. Further, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the ring-forming carbon number of the naphthalene ring. Therefore, the ring-forming carbon number of the naphthalene ring substituted with the alkyl group is 10.
- the number of ring-forming atoms is a compound having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, and a ring assembly) (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, and a carbocycle).
- atoms for example, a monocycle, a fused ring, and a ring assembly
- Atoms that do not form a ring for example, a hydrogen atom that terminates the bond of atoms that form a ring
- atoms included in the substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms.
- the "number of ring-forming atoms" described below shall be the same unless otherwise stated.
- the pyridine ring has 6 ring-forming atoms
- the quinazoline ring has 10 ring-forming atoms
- the furan ring has 5 ring-forming atoms.
- the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent is not included in the number of pyridine ring forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6.
- a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
- the number of carbon atoms XX to YY in the expression "the ZZ group having the number of carbon atoms XX to YY substituted or unsubstituted” represents the number of carbon atoms when the ZZ group is unsubstituted and is substituted. Does not include the carbon number of the substituent in the case.
- "YY” is larger than “XX”, “XX” means an integer of 1 or more, and "YY” means an integer of 2 or more.
- the number of atoms XX to YY in the expression "the ZZ group having the number of atoms XX to YY substituted or unsubstituted” represents the number of atoms when the ZZ group is unsubstituted and is substituted. Does not include the number of atoms of the substituent in the case.
- "YY” is larger than “XX”
- "XX” means an integer of 1 or more
- YY" means an integer of 2 or more.
- the unsubstituted ZZ group represents the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group", and the substituted ZZ group is the "substituted or unsubstituted ZZ group". Represents the case where is a "substitution ZZ group”.
- the term "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not replaced with the substituent.
- the hydrogen atom in the "unsubstituted ZZ group” is a light hydrogen atom, a heavy hydrogen atom, or a triple hydrogen atom.
- substitution in the case of “substituent or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with the substituent.
- substitution in the case of “BB group substituted with AA group” means that one or more hydrogen atoms in the BB group are replaced with the AA group.
- the ring-forming carbon number of the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise stated herein. ..
- the number of ring-forming atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise stated herein. be.
- the carbon number of the "unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.
- the carbon number of the "unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
- the carbon number of the "unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
- the ring-forming carbon number of the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise stated herein. be.
- the ring-forming carbon number of the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise stated herein. ..
- the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, and more preferably 5. ⁇ 18.
- the carbon number of the "unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.
- Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in the present specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). ) Etc. can be mentioned.
- the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group”
- the substituted aryl group is the "substituted or unsubstituted aryl group”.
- aryl group includes both "unsubstituted aryl group” and “substituted aryl group”.
- the "substituted aryl group” means a group in which one or more hydrogen atoms of the "unsubstituted aryl group” are replaced with a substituent.
- Examples of the “substituted aryl group” include a group in which one or more hydrogen atoms of the "unsubstituted aryl group” of the following specific example group G1A are replaced with a substituent, and a substituted aryl group of the following specific example group G1B. Examples are given.
- aryl group (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, Anthril group, Benzoanthril group, Phenantril group, Benzophenanthril group, Fenarenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group
- aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, Parakisilyl group, Meta-kisilyl group, Ortho-kisilyl group, Para-isopropylphenyl group, Meta-isopropylphenyl group, Ortho-isopropylphenyl group, Para-t-butylphenyl group, Meta-t-butylphenyl group, Ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-Dimethylfluorenyl group, 9,9-Diphenylfluorenyl group, 9,9-bis (4-methylphenyl) fluorenyl group, 9,9-bis (4-isopropylphenyl) fluorenyl group, 9,9-bis (4-t-butylphenyl) fluorenyl group, Cyanophenyl group, Triphenylsilylphen
- heterocyclic group is a cyclic group containing at least one heteroatom in the ring-forming atom.
- the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
- the "heterocyclic group” described herein is a monocyclic group or a fused ring group.
- the “heterocyclic group” described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
- Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in the present specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2). Specific example group G2B) and the like can be mentioned.
- the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is the "unsubstituted heterocyclic group", and the substituted heterocyclic group is "substituted or unsubstituted".
- heterocyclic group is "substituted heterocyclic group”.
- heterocyclic group is simply referred to as “unsubstituted heterocyclic group” and “substituted heterocyclic group”. Including both.
- substituted heterocyclic group means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group” are replaced with a substituent.
- substituted heterocyclic group examples include a group in which the hydrogen atom of the "unsubstituted heterocyclic group” of the following specific example group G2A is replaced, an example of the substituted heterocyclic group of the following specific example group G2B, and the like. Can be mentioned. It should be noted that the examples of the "unsubstituted heterocyclic group” and the “substituted heterocyclic group” listed here are merely examples, and the "substituted heterocyclic group” described in the present specification is specifically referred to as a "substituted heterocyclic group".
- the specific example group G2A is, for example, an unsubstituted heterocyclic group containing the following nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), and a non-substituted complex ring group containing a sulfur atom. (Specific example group G2A3) and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33). (Specific example group G2A4) is included.
- the specific example group G2B is, for example, a substituted heterocyclic group containing the following nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), and a substituted heterocycle containing a sulfur atom.
- the substituent is one or more hydrogen atoms of the group (specific example group G2B3) and the monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33). Includes replaced groups (specific example group G2B4).
- An unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazoleyl group, Oxazolyl group, Isooxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiasia Zoryl group, Pyridyl group, Pyridadinyl group, Pyrimidinyl group, Pyrazinel group, Triazinyl group, Indrill group, Isoin drill group, Indridinyl group, Kinolidinyl group, Quinoline group, Isoquinolyl group, Synnolyl group, Phthalazinyl group, Kinazolinyl group, Kinoxalinyl group, Benzoimidazolyl group, Indazolyl group, Phenantrolinyl group, Phenantridinyl group, Acridinyl group
- An unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): Frill group, Oxazolyl group, Isooxazolyl group, Oxadiazolyl group, Xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naftbenzofuranyl group, Benzodiazepine group, Benzoisoxazolyl group, Phenoxazinyl group, Morphorino group, Ginaftfuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group and diazanaphthobenzofuranyl group.
- An unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): Thienyl group, Thiazolyl group, Isothiazolyl group, Thiasia Zoryl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naftbenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzodiazepine azolyl group, Phenothiadinyl group, Dinaftthiophenyl group (dinaftthienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaft benzothiophenyl
- XA and YA are independently oxygen atom, sulfur atom, NH, or CH 2 . However, at least one of XA and YA is an oxygen atom, a sulfur atom, or NH.
- the general formulas (TEMP-16) to (TEMP - 33) when at least one of X A and YA is NH or CH 2 , the general formulas (TEMP-16) to (TEMP-33) are used.
- the monovalent heterocyclic group derived from the represented ring structure includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2 .
- -Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-Phenyl) carbazolyl group, (9-biphenylyl) carbazolyl group, (9-Phenyl) Phenylcarbazolyl group, (9-naphthyl) carbazolyl group, Diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methylbenzoimidazolyl group, Ethylbenzoimidazolyl group, Phenyltriazinyl group, Biphenyll triazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group and biphenylylquinazolinyl group.
- one or more hydrogen atoms of a monovalent heterocyclic group means that at least one of hydrogen atoms, XA and YA bonded to the ring - forming carbon atom of the monovalent heterocyclic group is NH. It means one or more hydrogen atoms selected from the hydrogen atom bonded to the nitrogen atom in the case of, and the hydrogen atom of the methylene group in the case where one of XA and YA is CH 2 .
- Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in the present specification include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). ).
- the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is the "unsubstituted alkyl group”
- the substituted alkyl group is the "substituted or unsubstituted alkyl group”.
- alkyl group includes both "unsubstituted alkyl group” and "substituted alkyl group”.
- the "substituted alkyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
- Specific examples of the "substituted alkyl group” include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with a substituent, and a substituted alkyl group (specific example). Examples of group G3B) can be mentioned.
- the alkyl group in the "unsubstituted alkyl group” means a chain-like alkyl group. Therefore, the "unsubstituted alkyl group” includes a linear "unsubstituted alkyl group” and a branched "unsubstituted alkyl group”.
- the examples of the "unsubstituted alkyl group” and the “substituted alkyl group” listed here are only examples, and the "substituted alkyl group” described in the present specification includes the specific example group G3B.
- Unsubstituted alkyl group (specific example group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, Isobutyl group, s-Butyl group and t-Butyl group.
- -Alkyl group of substitution (specific example group G3B): Propylfluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group.
- Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in the present specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group). G4B) and the like can be mentioned.
- the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group” is a "substituted alkenyl group", and the "substituted alkenyl group” is a "substituted or unsubstituted alkenyl group”. Refers to the case where "is a substituted alkenyl group”.
- alkenyl group includes both "unsubstituted alkenyl group” and "substituted alkenyl group”.
- the "substituted alkenyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group” are replaced with a substituent.
- Specific examples of the "substituted alkenyl group” include a group in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, an example of a substituted alkenyl group (specific example group G4B), and the like. Be done.
- the examples of the "unsubstituted alkenyl group” and the “substituted alkenyl group” listed here are only examples, and the "substituted alkenyl group” described in the present specification includes the specific example group G4B.
- Unsubstituted alkenyl group (specific example group G4A): Vinyl group, Allyl group, 1-butenyl group, 2-butenyl group and 3-butenyl group.
- Substituent alkenyl group (specific example group G4B): 1,3-Butandienyl group, 1-Methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-Methylallyl group and 1,2-dimethylallyl group.
- alkynyl groups and “substituted alkynyl groups”.
- the "substituted alkynyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group” are replaced with a substituent.
- Specific examples of the "substituted alkynyl group” include a group in which one or more hydrogen atoms are replaced with a substituent in the following "unsubstituted alkynyl group” (specific example group G5A).
- Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in the present specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6A). Specific example group G6B) and the like can be mentioned.
- the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group is "substituted or unsubstituted”. Refers to the case where the "cycloalkyl group” is a "substituted cycloalkyl group”.
- the term “cycloalkyl group” is simply referred to as "unsubstituted cycloalkyl group” and "substituted cycloalkyl group”. Including both.
- the "substituted cycloalkyl group” means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group” are replaced with a substituent.
- Specific examples of the "substituted cycloalkyl group” include a group in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group” (specific example group G6A) are replaced with a substituent, and a substituted cycloalkyl group. Examples of (Specific example group G6B) can be mentioned.
- cycloalkyl group (specific example group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
- Substituent cycloalkyl group (specific example group G6B): 4-Methylcyclohexyl group.
- group G7 of the group represented by —Si (R 901 ) (R 902 ) (R 903 ) described in the present specification, -Si (G1) (G1) (G1), -Si (G1) (G2) (G2), -Si (G1) (G1) (G2), -Si (G2) (G2) (G2), -Si (G3) (G3) (G3), and -Si (G6) (G6) (G6) (G6) Can be mentioned.
- G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
- G2 is the “substituted or unsubstituted heterocyclic group” described in the specific example group G2.
- G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.
- G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
- -A plurality of G1s in Si (G1) (G1) (G1) are the same as or different from each other.
- -A plurality of G2s in Si (G1) (G2) (G2) are the same as or different from each other.
- -A plurality of G1s in Si (G1) (G1) (G2) are the same as or different from each other.
- -A plurality of G2s in Si (G2) (G2) (G2) are the same as or different from each other.
- -A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
- -A plurality of G6s in Si (G6) (G6) (G6) are the same as or different from each other.
- G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
- G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
- G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
- G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
- G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
- G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
- G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
- G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
- G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
- G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
- G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
- G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
- -The plurality of G1s in N (G1) (G1) are the same as or different from each other.
- -The plurality of G2s in N (G2) (G2) are the same as or different from each other.
- -The plurality of G3s in N (G3) (G3) are the same as or different from each other.
- -The plurality of G6s in N (G6) (G6) are the same as or different from each other.
- Halogen atom Specific examples of the “halogen atom” described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
- the "unsubstituted fluoroalkyl group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
- the "substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the "fluoroalkyl group” are replaced with a substituent.
- the "substituted fluoroalkyl group” described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and a group.
- substituted fluoroalkyl group also included is a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group” are further replaced with the substituent.
- substituents in the "substituted fluoroalkyl group” include an example of a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a fluorine atom.
- the "unsubstituted haloalkyl group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
- the "substituted haloalkyl group” means a group in which one or more hydrogen atoms of the "haloalkyl group” are replaced with a substituent.
- the "substituted haloalkyl group” described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent, and a "substitution".
- haloalkyl group groups in which one or more hydrogen atoms of the substituents in the "haloalkyl group” are further replaced by the substituents.
- substituents include an example of a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
- the haloalkyl group may be referred to as a halogenated alkyl group.
- a specific example of the "substituted or unsubstituted alkoxy group” described in the present specification is a group represented by —O (G3), where G3 is the “substituted or substituted” described in the specific example group G3. It is an unsubstituted alkyl group.
- the "unsubstituted alkoxy group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
- a specific example of the "substituted or unsubstituted alkylthio group” described in the present specification is a group represented by —S (G3), where G3 is the “substituted or substituted” described in the specific example group G3. It is an unsubstituted alkyl group.
- the "unsubstituted alkylthio group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
- a specific example of the "substituted or unsubstituted aryloxy group” described in the present specification is a group represented by —O (G1), where G1 is the “substitution” described in the specific example group G1. Alternatively, it is an unsubstituted aryl group.
- the ring-forming carbon number of the "unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
- a specific example of the "substituted or unsubstituted arylthio group” described in the present specification is a group represented by —S (G1), where G1 is the “substituted or substituted” described in the specific example group G1. It is an unsubstituted aryl group.
- the ring-forming carbon number of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
- a specific example of the "trialkylsilyl group” described in the present specification is a group represented by ⁇ Si (G3) (G3) (G3), where G3 is described in the specific example group G3. It is a "substituted or unsubstituted alkyl group”.
- -A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
- the carbon number of each alkyl group of the "trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.
- a specific example of the "substituted or unsubstituted aralkyl group” described in the present specification is a group represented by-(G3)-(G1), where G3 is described in the specific example group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
- the "aralkyl group” is a group in which the hydrogen atom of the "alkyl group” is replaced with the "aryl group” as a substituent, and is an embodiment of the "substituted alkyl group".
- the "unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group” is unless otherwise specified herein. , 7 to 50, preferably 7 to 30, and more preferably 7 to 18.
- substituted or unsubstituted aralkyl group examples include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group and an ⁇ .
- -Naphtylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group and the like.
- substituted or unsubstituted aryl groups described herein are preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-unless otherwise described herein.
- the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzoimidazolyl group, a phenyl group, unless otherwise specified herein.
- Nantrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , Dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl) carbazolyl group ((9-phenyl) carbazole-1-yl group, (9-phenyl) carbazole-2-yl group, (9-phenyl) carbazole-3-yl group, or (9-phenyl) carbazole group -4-yl group), (9-bi
- carbazolyl group is specifically one of the following groups unless otherwise described in the present specification.
- the (9-phenyl) carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.
- dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups unless otherwise described in the present specification.
- Substituentally substituted or unsubstituted alkyl groups described herein are preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-, unless otherwise stated herein. It is a butyl group or the like.
- the "substituted or unsubstituted arylene group” described herein is derived by removing one hydrogen atom on the aryl ring from the above "substituted or unsubstituted aryl group” 2 It is the basis of the price.
- the "substituted or unsubstituted arylene group” (specific example group G12) one hydrogen atom on the aryl ring is removed from the "substituted or unsubstituted aryl group” described in the specific example group G1. Examples include the induced divalent group.
- the "substituted or unsubstituted divalent heterocyclic group" described in the present specification shall exclude one hydrogen atom on the heterocycle from the above "substituted or unsubstituted heterocyclic group”. It is a divalent group derived by.
- specific example group G13 of the "substituted or unsubstituted divalent heterocyclic group"
- Examples thereof include a divalent group derived by removing an atom.
- the "substituted or unsubstituted alkylene group” described herein is derived by removing one hydrogen atom on the alkyl chain from the above "substituted or unsubstituted alkyl group” 2 It is the basis of the price.
- the "substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group" described in the specific example group G3. Examples include the induced divalent group.
- the substituted or unsubstituted arylene group described in the present specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise described in the present specification.
- Q1 to Q10 are independently hydrogen atoms or substituents, respectively.
- * represents a binding position.
- Q1 to Q10 are independently hydrogen atoms or substituents, respectively.
- the formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
- * represents a binding position.
- the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably a group according to any one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise described in the present specification. Is.
- Q1 to Q9 are independently hydrogen atoms or substituents, respectively.
- Q1 to Q8 are independently hydrogen atoms or substituents, respectively.
- the set of two adjacent sets is one set. Is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925 , and R 925 .
- the above-mentioned "one or more sets” means that two or more sets of two or more adjacent sets may form a ring at the same time.
- R 921 and R 922 are coupled to each other to form ring Q A
- R 925 and R 926 are coupled to each other to form ring Q B
- the above general formula (TEMP-103) is used.
- the anthracene compound represented is represented by the following general formula (TEMP-104).
- anthracene compound represented by the general formula (TEMP-103) is described below. It is represented by the general formula (TEMP-105). In the following general formula (TEMP-105), ring QA and ring QC share R922 .
- the formed “monocycle” or “condensed ring” may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “a set of two adjacent sets” forms a “monocycle” or a “condensed ring”, the “monocycle” or “condensed ring” is a saturated ring or a ring of saturation.
- An unsaturated ring can be formed.
- the ring QA and the ring QB formed in the general formula (TEMP - 104) are “single ring” or “condensed ring", respectively.
- the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “condensed rings”.
- the ring Q A and the ring Q C of the general formula (TEMP-105) are formed into a fused ring by condensing the ring Q A and the ring Q C. If the ring QA of the general formula ( TMEP - 104) is a benzene ring, the ring QA is a monocyclic ring. If the ring QA of the general formula ( TMEP - 104) is a naphthalene ring, the ring QA is a fused ring.
- the "unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle.
- saturated ring is meant an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
- aromatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G1 is terminated by a hydrogen atom.
- aromatic heterocycle include a structure in which the aromatic heterocyclic group given as a specific example in the specific example group G2 is terminated by a hydrogen atom.
- Specific examples of the aliphatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom.
- forming a ring is meant forming a ring with only a plurality of atoms in the matrix, or with a plurality of atoms in the matrix and one or more arbitrary elements.
- the ring QA formed by bonding R 921 and R 922 to each other which is represented by the general formula (TEMP-104), has a carbon atom of an anthracene skeleton to which R 921 is bonded and an anthracene to which R 922 is bonded. It means a ring formed by a carbon atom of a skeleton and one or more arbitrary elements.
- a carbon atom of an anthracene skeleton to which R 921 is bonded a carbon atom of an anthracen skeleton to which R 922 is bonded, and four carbon atoms.
- the ring formed by R 921 and R 922 is a benzene ring.
- arbitrary element is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise described in the present specification.
- the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent” described later.
- the formed ring is a heterocycle.
- the number of "one or more arbitrary elements" constituting the monocyclic or condensed ring is preferably 2 or more and 15 or less, and more preferably 3 or more and 12 or less. , More preferably 3 or more and 5 or less.
- the "monocycle” and the “condensed ring” are preferably “monocycles”.
- the "saturated ring” and the “unsaturated ring” are preferably “unsaturated rings”.
- a “monocycle” is preferably a benzene ring.
- the "unsaturated ring” is preferably a benzene ring.
- one or more pairs of two or more adjacent pairs are bonded to each other to form a plurality of atoms in the mother skeleton and one or more 15 elements. It forms a substituted or unsubstituted "unsaturated ring” consisting of at least one element selected from the group consisting of the following carbon element, nitrogen element, oxygen element, and sulfur element.
- the substituent is, for example, an "arbitrary substituent” described later.
- Specific examples of the substituent when the above-mentioned “monocycle” or “condensed ring” has a substituent are the substituents described in the above-mentioned “Substituents described in the present specification” section.
- the substituent is, for example, an "arbitrary substituent” described later.
- substituents when the above-mentioned "monocycle” or “condensed ring” has a substituent are the substituents described in the above-mentioned “Substituents described in the present specification” section.
- the above is the case where “one or more sets of two or more adjacent sets are combined with each other to form a substituted or unsubstituted monocycle” and “one or more sets of two or more adjacent sets”.
- R 901 to R 907 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. When two or more R 901s are present, the two or more R 901s are the same as or different from each other.
- the two or more R 902s are the same as or different from each other. If there are two or more R 903s , the two or more R 903s are the same as or different from each other. If there are two or more R 904s , the two or more R 904s are the same as or different from each other. If there are two or more R 905s , the two or more R 905s are the same as or different from each other. If there are two or more R- 906s , the two or more R- 906s are the same as or different from each other. When two or more R 907s are present, the two or more R 907s are the same as or different from each other.
- the substituent in the case of "substitutable or unsubstituted" is Alkyl group with 1 to 50 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 50 ring-forming carbon atoms and a heterocyclic group having 5 to 50 ring-forming atoms.
- the substituent in the case of "substitutable or unsubstituted" is Alkyl groups with 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring-forming carbon atoms and a heterocyclic group having 5 to 18 ring-forming atoms.
- any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably substituted or unsaturated 5 It forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. do.
- any substituent may further have a substituent.
- the substituent further possessed by the arbitrary substituent is the same as that of the above-mentioned arbitrary substituent.
- the numerical range expressed by using “AA to BB” has the numerical value AA described before “AA to BB” as the lower limit value and the numerical value BB described after “AA to BB”. Means the range including as the upper limit value.
- the formula represented by "A ⁇ B” means that the value of A and the value of B are equal to each other, or the value of A is larger than the value of B.
- the formula represented by "A ⁇ B” means that the value of A and the value of B are equal to each other, or the value of A is smaller than the value of B.
- the organic electroluminescence element of the present embodiment has a cathode, an anode, a light emitting region arranged between the cathode and the anode, and a hole transport band arranged between the anode and the light emitting region.
- the light emitting region includes at least one light emitting layer, the at least one light emitting layer is a first light emitting layer, and the hole transport band includes a first anode-side organic layer and a second light emitting layer.
- the first anode-side organic layer is in direct contact with the second anode-side organic layer, and the first anode-side organic layer and the second anode-side organic layer are in direct contact with the second anode-side organic layer.
- the layers are arranged in the order of the first anode-side organic layer and the second anode-side organic layer from the anode side between the anode and the light emitting region, and the first anode-side organic layer is
- the first organic material and the second organic material contain the first organic material and the second organic material, and the first organic material and the second organic material are different from each other, and the first organic material in the first anode-side organic layer is different from each other.
- the content of the organic material is less than 50% by mass, and the second organic material has a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a substituted or unsubstituted amino group in the molecule.
- the second anode-side organic layer contains a second hole transport band material, and the second hole transport band material contains a substituted or unsubstituted amino group. It is a monoamine compound having one in the molecule or a diamine compound having two substituted or unsubstituted amino groups in the molecule, and the second hole transport zone material and the first organic material are different from each other.
- the second hole transport zone material and the second organic material are the same as or different from each other, and the first light emitting layer is a fluorescent light emitting layer, and the first light emitting layer is described.
- the refractive index NM 1 of the constituent material contained in the organic layer on the anode side and the refractive index NM 2 of the constituent material contained in the second organic layer on the anode side satisfy the relationship of the following formula (several NM). NM 1 > NM 2 ... (number NM)
- the element performance of the organic EL element can be improved.
- the luminous efficiency of the organic EL element is improved.
- the life of the organic EL device is extended.
- the region consisting of a plurality of organic layers arranged between the anode and the light emitting region is referred to as a hole transport zone.
- the anode and the hole transport band are in direct contact with each other, and the light emitting region and the hole transport band are in direct contact with each other.
- the hole transport zone includes at least a first anode-side organic layer and a second anode-side organic layer.
- the refractive index NM 1 of the constituent material contained in the first anode-side organic layer and the refractive index NM 2 of the constituent material contained in the second anode-side organic layer are By satisfying the relationship of the above formula (number NM), the light extraction efficiency of the organic EL element is improved.
- the refractive index NM 1 of the constituent material contained in the first anode-side organic layer is the refractive index of a mixture composed of the compounds (at least the first organic material and the second organic material) contained in the first anode-side organic layer. Corresponds to.
- the refractive index NM 2 of the constituent material contained in the second anode-side organic layer corresponds to the refractive index of the kind of compound
- the refractive index of the constituent materials contained in the other organic layers is defined in the same manner as these. The refractive index can be measured by the measuring method described in Examples described later.
- the refractive index NM 1 of the constituent material contained in the first anode-side organic layer and the refractive index NM 2 of the constituent material contained in the second anode-side organic layer satisfies the relationship of the following mathematical formula (number NM 1). NM 1 -NM 2 ⁇ 0.01 ... (Number NM1)
- the refractive index NM 1 of the constituent material contained in the first anode-side organic layer and the refractive index NM 2 of the constituent material contained in the second anode-side organic layer satisfies the relationship of the following formula (number NM2), formula (number NM3) or formula (number NM4).
- NM 1 -NM 2 ⁇ 0.05... (number NM2)
- NM 1 -NM 2 ⁇ 0.075...
- number NM3 NM 1 -NM 2 ⁇ 0.10 ... (Number NM4)
- the refractive index NM 1 of the constituent material contained in the first anode-side organic layer is 1.90 or more. In one aspect of the organic EL device of the present embodiment, the refractive index of the second organic material contained in the first anode-side organic layer is 1.90 or more.
- the refractive index NM 1 of the constituent material contained in the first anode-side organic layer is 1.94 or more. In one aspect of the organic EL device of the present embodiment, the refractive index of the second organic material contained in the first anode-side organic layer is 1.94 or more.
- the refractive index NM 2 of the constituent material contained in the second anode-side organic layer is 1.89 or less. In one aspect of the organic EL device of the present embodiment, the refractive index of the second hole transport band material contained in the second anode-side organic layer is 1.89 or less.
- the hole transport band includes only the first anode-side organic layer and the second anode-side organic layer.
- the total film thickness of the hole transport zone corresponds to the sum of the film thickness of the first anode-side organic layer and the film thickness of the second anode-side organic layer.
- the film thickness of the first anode-side organic layer is 20 nm or less.
- the film thickness of the second anode-side organic layer is 30 nm or more and 150 nm or less. In one aspect of the organic EL device of the present embodiment, the film thickness of the second anode-side organic layer is 30 nm or more and 80 nm or less. In one aspect of the organic EL device of the present embodiment, the film thickness of the second anode-side organic layer is 80 nm or more and 150 nm or less.
- the ratio of the film thickness of the first anode-side organic layer to the film thickness of the second anode-side organic layer preferably has the relationship of the following mathematical formula (Equation A1). Satisfy, and more preferably satisfy the relationship of the following mathematical formula (number A2). 2.0 ⁇ TL 2 / TL 1 ⁇ 30 ... (number A1) 8.0 ⁇ TL 2 / TL 1 ⁇ 16 ... (number A2) (TL 1 is the film thickness of the first anode-side organic layer, TL 2 is the film thickness of the second anode-side organic layer, and the unit of the film thickness is nm.)
- the first anode-side organic layer is in direct contact with the anode.
- the hole transport band consists of only the first anode-side organic layer and the second anode-side organic layer
- the second anode-side organic layer and the light emitting region are I am in direct contact with you.
- the first anode-side organic layer does not contain the compound contained in the second anode-side organic layer.
- the first anode-side organic layer is the first organic material, and the compound CA and the second organic material are used.
- the present invention includes an embodiment in which two kinds of the compound CB are contained, and the second anode-side organic layer contains one kind of the compound AA. Since both the compound CA and the compound CB contained in the first anode-side organic layer are different from the compound AA, the conditions are satisfied.
- the first anode-side organic layer contains two kinds of compound CA and compound CB and the second anode-side organic layer contains one kind of compound CB
- the first anode with respect to compound CB Since the side organic layer and the second anode side organic layer contain the same compound, the above conditions are not satisfied.
- the compound contained in the first anode-side organic layer is different from the compound contained in the second anode-side organic layer.
- the second anode-side organic layer contains one kind of the compound AA, and the first one.
- the anode-side organic layer contains two kinds of compound CA and compound CB can be mentioned.
- the second anode-side organic layer contains two kinds of compound AA and compound AB
- the first anode-side organic layer contains two kinds of compound CA and compound CB
- the second anode-side organic layer contains one kind of compound AA and the first anode-side organic layer contains two kinds of compound CA and compound AA, the first anode with respect to compound AA. Since the side organic layer and the second anode side organic layer contain the same compound, the above conditions are not satisfied.
- the second organic material contained in the first anode-side organic layer is a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a substituted or unsubstituted amino. It is a diamine compound having two groups in the molecule.
- the nitrogen atom of the amino group is not a ring-forming atom.
- the nitrogen atom is a ring-forming atom such as a carbazole ring and an azine ring, the nitrogen atom is not a nitrogen atom as an amino group.
- the following compound HT-X contains two nitrogen atoms in the molecule, one nitrogen atom in HT-X is a ring-forming atom of a carbazole ring, and the other nitrogen atom is a ring-forming atom. Not a nitrogen atom as an amino group.
- the following compound HT-X is a compound having a structure in which a 9-phenyl-3-carbazolyl group is bonded to a nitrogen atom of an amino group via a linking group, and is a monoamine compound.
- the following compound HT-Y is also a compound having a structure in which a 9-carbazolyl group is bonded to a nitrogen atom of an amino group via a linking group, and is a monoamine compound.
- the second organic material contained in the first anode-side organic layer is a compound represented by the following general formula (cHT2-1), the general formula (cHT2-2). It is at least one compound selected from the group consisting of the compound represented by and the compound represented by the general formula (cHT2-3).
- Ar 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 and Ar 124 are independent of each other.
- Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms A substituted or unsubstituted heterocyclic group having 5 to 50 atom-forming atoms, or ⁇ Si ( RC1 ) ( RC2 ) ( RC3 ).
- RC1 , RC2, and RC3 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
- the plurality of RC1s are the same as or different from each other.
- the plurality of RC2s are the same as or different from each other.
- the plurality of RC3s are the same as or different from each other.
- LA1 , LA2 , LA3 , LB1 , LB2 , LB3 and LB4 are independent of each other.
- nb is 1, 2, 3 or 4
- LB5 is It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- nb is 2, 3 or 4
- the plurality of LB5s are the same as or different from each other.
- LB5s When nb is 2, 3 or 4, a plurality of LB5s are Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other
- the LB5 that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring is It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- RA35 and RA36 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- RA25 and RA35 and RA36 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independent of each other.
- Hydrogen atom, Cyano group Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkyl halide groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- One or more of the two or more adjacent pairs of RA20 to RA24 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- One or more of the two or more adjacent pairs of RA30 to RA34 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- RA20 to RA24 and RA30 to RA34 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independent of each other.
- Hydrogen atom, Cyano group Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkyl halide groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R901 to R904 are independently. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the second amino group represented by is the same group or a different group.
- the compound represented by the general formula (cHT2-1), the general formula (cHT2-2) and the general formula (cHT2-3) is "substituted or unsubstituted".
- the substituent is not the group represented by -N ( RC6) (RC7 ) .
- RC6 and RC7 are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, respectively.
- substituent in the case of "substitution or non-substitution" is not a group represented by -N (RC6) ( RC7 ), it is represented by the above general formulas ( cHT2-1 ) and general formula (cHT2-2).
- the compound to be used is a monoamine compound.
- the second organic material is a monoamine compound having one substituted or unsubstituted amino group in the molecule.
- the compound represented by the general formula (cHT2-1) and the compound represented by the general formula (cHT2-2) are monoamine compounds.
- the second organic material as a compound contained in the first anode-side organic layer is a diamine compound having two substituted or unsubstituted amino groups in the molecule. ..
- the compound represented by the general formula (cHT2-3) is a diamine compound.
- the second organic material is a triamine compound having three substituted or unsubstituted amino groups in the molecule.
- the second organic material is a tetraamine compound having four substituted or unsubstituted amino groups in the molecule.
- the compound represented by the general formula (cHT2-1) and the general formula (cHT2-2) is a triamine compound
- the compound represented by the general formula (cHT2-1) and the general formula (cHT2-2) is used.
- the compound represented by the general formula (cHT2-1) and the general formula (cHT2-2) is a tetraamine compound
- the compound represented by the general formula (cHT2-1) is "substituted or unsubstituted".
- it has three groups represented by -N ( RC6) (RC7 ) .
- the compound represented by the general formula (cHT2-3) is a triamine compound
- the compound represented by the general formula (cHT2-3) is used as a substituent in the case of "substituted or unsubstituted". It has one group represented by N ( RC6) (RC7 ) .
- the compound represented by the general formula (cHT2-3) is a tetraamine compound
- the compound represented by the general formula (cHT2-1) is used as a substituent in the case of "substituted or unsubstituted". It has two groups represented by N ( RC6) (RC7 ) .
- the second organic material is a compound represented by the general formula (cHT2-1), a compound represented by the general formula (cHT2-2), and a general formula (cHT2). It is at least one compound selected from the group consisting of the compounds represented by -3).
- the second organic material is a group represented by the following general formula (2-a), a group represented by the general formula (2-b), and a general formula (2).
- the second organic material is a compound represented by the general formula (cHT2-1), a compound represented by the general formula (cHT2-2), and a general formula (cHT2). It is at least one compound selected from the group consisting of the compounds represented by -3), and is in the general formula (cHT2-1), the general formula (cHT2-2) and the general formula (cHT2-3).
- At least one of Ar 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 and Ar 124 is a group represented by the following general formula (2-a), a group represented by the general formula (2-b), and the like.
- R251 to R255 are independent of each other.
- R261 to R268 is a single bond that binds to * b.
- R 261 to R 268 which are not single bonds bound to b, are independent of each other.
- Hydrogen atom A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. ** represents the bonding position.
- R 271 to R 282 is a single bond that binds to * c. * None of the pairs consisting of two or more adjacent R 271 to R 282 that are not single bonds bound to c do not bind to each other. * R 271 to R 282 , which are not single bonds bound to c, are independent of each other. Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. ** represents the bonding position. )
- R 291 to R 300 is a single bond that binds to * d.
- R 291 to R 300 which are not single bonds bound to d, are independent of each other.
- Hydrogen atom A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. ** represents the bonding position.
- ** is, for example, at least of Ar 112 , Ar 113 , Ar 121 , Ar 122 , Ar 123 and Ar 124 in the general formula (cHT2-1), the general formula (cHT2-2) and the general formula (cHT2-3). It may be a bond position that binds to any of them.
- Z 3 is an oxygen atom, a sulfur atom, NR 319 or C (R 320 ) (R 321 ).
- R 311 to R 321 is a single bond that binds to * e, or a pair of two or more adjacent pairs of R 311 to R 318 are bonded to each other to form the following substitutions or non-replacements.
- Any carbon atom of the benzene ring of the above is bonded to * e with a single bond, * A pair consisting of two or more adjacent R 311 to R 318 that is not a single bond that binds to e Bond to each other to form substituted or unsubstituted benzene rings, or not to each other * R 311 to R 318 , which are not single bonds bonded to e and do not form the substituted or unsubstituted benzene ring, are independently.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 10 ring-forming atoms.
- R 319 which is not a single bond that binds to e, Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms.
- R 320 and R 321 that is not a single bond that binds to e Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 320 and R 321 which are not single bonds bonded to e and do not form the substituted or unsubstituted single ring and do not form the substituted or unsubstituted fused ring are independently of each other.
- Hydrogen atom A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. ** represents the bonding position. )
- R 341 to R 345 is a single bond that binds to * h1
- the other one of R 341 to R 345 is a single bond that binds to * h2. None of the pairs consisting of two or more adjacent R 341 to R 345 that are not single bonds that bind to * h1 and are not single bonds that bind to * h2 do not bind to each other.
- One or more of the two or more adjacent pairs of R 351 to R 355 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 361 to R 365 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 341 to R 345 which are not single bonds bound to * h1 and are not single bonds bound to * h2, and the substituted or unsubstituted fused rings that do not form the substituted or unsubstituted monocycle.
- R 351 to R 355 and R 361 to R 365 that do not form are independent of each other.
- Hydrogen atom A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. ** represents the bonding position. )
- the second organic material is a monoamine compound having one substituted or unsubstituted amino group in the molecule, and is represented by the above general formula (2-a).
- the group to be treated and the group represented by the general formula (2-f) are independently bonded directly to the nitrogen atom of the amino group of the monoamine compound, bonded via a phenylene group, or bonded to each other. It binds via a biphenylene group.
- R 312 or R 317 is a single bond that binds to * e.
- the group represented by the general formula (2-e) is a group represented by the following general formula (2-e7).
- R 311 to R 316 , R 318 and R 319 are synonymous with R 311 to R 316 , R 318 and R 319 in the general formula (2-e), respectively. , ** represent the bond position.
- R 315 , R 316 or R 318 is a single bond bonded to * e.
- the group represented by the general formula (2-e) is the following general formula (2-e4), general formula (2-e5) or general formula (2-e6). ) Is the group represented by.
- R 311 to R 319 are R 311 to R 319 in the general formula (2-e), respectively. It is synonymous with **, and ** represents the connection position.
- the group represented by the general formula (2-e) is the following general formula (2-e1), general formula (2-e2) or general formula (2-e3). ) Is the group represented by.
- Z 3 is an oxygen atom, a sulfur atom, NR 319 or C (R 320 ) (R 321 ).
- R 311 to R 325 is a single bond that binds to * e. * R 311 to R 318 and R 322 to R 325 , which are not single bonds bound to e, are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 10 ring-forming atoms.
- R 319 which is not a single bond that binds to e, Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms.
- R 320 and R 321 that is not a single bond that binds to e Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 320 and R 321 which are not single bonds bonded to e and do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring are independently of each other.
- Hydrogen atom A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. ** represents the bonding position. )
- the compound contained in the first anode-side organic layer is a compound that does not contain a thiophene ring in the molecule.
- the second organic material as a compound contained in the first anode-side organic layer may be referred to as a first hole transport band material.
- the content of the first organic material in the first anode-side organic layer is less than 50% by mass. In one aspect of the organic EL device of the present embodiment, the content of the first organic material in the first anode-side organic layer is 15% by mass or less. In one aspect of the organic EL device of the present embodiment, the content of the first organic material in the first anode-side organic layer is 5% by mass or more.
- the content of the first organic material in the first anode-side organic layer is 30% by mass or less, 20% by mass or less, or 15% by mass. % Or less.
- the content of the second organic material in the first anode-side organic layer is more than 50% by mass, 70% by mass or more, or 80% by mass. It is more than or equal to 85% by mass or more. In one aspect of the organic EL device of the present embodiment, the content of the second organic material in the first anode-side organic layer is 95% by mass or less. The total content of the first organic material and the second organic material in the first anode-side organic layer is 100% by mass or less.
- the first anode-side organic layer contains a dope compound as the first organic material, and the first hole transport band material as the second organic material. contains.
- the doped compound is at least one of a first ring structure represented by the following general formula (P11) and a second ring structure represented by the following general formula (P12). It is a compound containing.
- the first ring structure represented by the general formula (P11) is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon ring in the molecule of the doped compound. It is fused with at least one of the ring structures of a heterocycle having 5 to 50 ring-forming atoms.
- R 11 to R 14 and R 1101 to R 1110 are independent of each other.
- Z 1 to Z 5 are independent of each other. Nitrogen atom, A carbon atom bonded to R15 or a carbon atom bonded to another atom in the molecule of the doped compound. At least one of Z 1 to Z 5 is a carbon atom bonded to another atom in the molecule of the doped compound.
- R15 is Hydrogen atom, Halogen atom, Cyano group, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkyl halide groups having 1 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Substituent or unsubstituted alkenyl groups having 2 to
- R901 to R907 are independently, respectively.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are the same as or different from each other.
- the ester group in the present specification is at least one group selected from the group consisting of an alkyl ester group and an aryl ester group.
- RE is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).
- R Ar is, for example, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- the siroxanyl group in the present specification is a silicon compound group via an ether bond, for example, a trimethylsiloxanyl group.
- the carbamoyl group herein is represented by -CONH 2 .
- the substituted carbamoyl group herein is represented by, for example, -CONH-Ar C , or -CONH- RC .
- Ar C is, for example, an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms (preferably 6 to 10 ring-forming carbon atoms) and 5 to 50 ring-forming atoms (preferably 5 to 14 ring-forming atoms). ) Is at least one of the groups selected from the group consisting of heterocyclic groups.
- Ar C may be a group in which an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms and a substituted or unsubstituted ring-forming atomic number 5 to 50 heterocyclic group are bonded.
- RC is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).
- the groups described as "substituted or unsubstituted" are preferably "unsubstituted" groups.
- the second organic material is a monoamine compound having only one substituted or unsubstituted amino group in the molecule.
- the second organic material is selected from the group consisting of the compound represented by the general formula (cHT2-1) and the compound represented by the general formula (cHT2-2). Contains at least one of the following compounds.
- the compound represented by the general formula (cHT2-1) and the compound represented by the general formula (cHT2-2) as the second organic material are monoamine compounds. be.
- the second hole transport zone material is a monoamine compound having one substituted or unsubstituted amino group in the molecule, or two substituted or unsubstituted amino groups in the molecule. It is a diamine compound having.
- the second hole transport zone material is a monoamine compound having one substituted or unsubstituted amino group in the molecule.
- the second hole transport band material is selected from the group consisting of the compound represented by the following general formula (C1) and the compound represented by the following general formula (C3). At least one of the compounds to be made.
- Ar 311 and Ar 312 and Ar 313 are independent of each other.
- Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms A substituted or unsubstituted heterocyclic group having 5 to 50 atom-forming atoms, or ⁇ Si ( RC1 ) ( RC2 ) ( RC3 ).
- RC1 , RC2, and RC3 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
- the plurality of RC1s are the same as or different from each other.
- L D1 , L D2 and L D3 are independent of each other. Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- LC1 , LC2 , LC3 and LC4 are independent of each other. Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- n2 is 1, 2, 3 or 4
- LC5 is It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- n2 is 2, 3 or 4
- the plurality of LC5s are the same as or different from each other.
- a plurality of LC5s are Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other
- the LC5 that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring is It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 131 , Ar 132 , Ar 133 and Ar 134 are independent of each other.
- Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms A substituted or unsubstituted heterocyclic group having 5 to 50 atom-forming atoms, or ⁇ Si ( RC1 ) ( RC2 ) ( RC3 ).
- RC1 , RC2, and RC3 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
- the plurality of RC1s are the same as or different from each other.
- the plurality of RC2s are the same as or different from each other.
- the plurality of RC3s are the same as or different from each other.
- the first amino group represented by the following general formula (C3-1) and the second amino group represented by the following general formula (C3-2) are the same group or different groups. .. )
- the substituent in the case of "substituted or unsubstituted” is -N ( RC6) (RC7 ) . It is not a group to be represented.
- the substituent in the case of "substituted or unsubstituted” is -N ( RC6) (RC7 ) . It is not a group to be represented.
- RC6 and RC7 are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, respectively.
- the compound represented by the general formula (C1) is represented by the compound represented by the following general formula (cHT3-1) and the general formula (cHT3-2). It is at least one compound selected from the group consisting of a compound, a compound represented by the general formula (cHT3-3) and a compound represented by the general formula (cHT3-4).
- Ar 312 , Ar 313 , LD1 , LD2 and LD3 are independently synonymous with Ar 312 , Ar 313 , LD1 , LD2 and LD3 in the general formula (C1).
- Ar 311 is a group represented by any of the following general formulas (1-a), general formula (1-b), general formula (1-c) and general formula (1-d).
- One or more of the two or more adjacent pairs of RD20 to RD24 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- One or more of the two or more adjacent pairs of RD31 to RD38 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- One or more of the two or more adjacent pairs of R D40 to R D44 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- X 3 is an oxygen atom, a sulfur atom or C ( RD45 ) ( RD46 ).
- the set consisting of R D45 and R D46 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R D25 , R D20 to R D24 , R D31 to R D38 , R D40 to R D44 , R D45 and R which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring.
- D46 is independent of each other Hydrogen atom, Cyano group, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkyl halide groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- Multiple RD20s are the same as or different from each other
- Multiple RD40s are the same as or different from each other
- R901 to R904 in the compounds represented by the general formula (cHT3-1), the general formula (cHT3-2), the general formula (cHT3-3) and the general formula (cHT3-4) are independent of each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- R 51 to R 55 are independently hydrogen atoms or substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms. ** represents the bonding position with LD1 .
- R 61 to R 68 is a single bond that binds to * b. * None of the pairs consisting of two or more adjacent R 61 to R 68 that are not single bonds bound to b are bound to each other. * R 61 to R 68 , which are not single bonds bonded to b, are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or substituted or unsubstituted ring-forming carbon atoms having 6 to 12 carbon atoms. It is an aryl group and ** represents the bonding position with LD1 . )
- R 71 to R 80 is a single bond that binds to * d. * None of the pairs of two or more adjacent R 71 to R 80 that are not single bonds bound to d are bound to each other.
- R 71 to R 80 which are not single bonds bonded to d, are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or substituted or unsubstituted ring-forming carbon atoms having 6 to 12 carbon atoms. It is an aryl group and ** represents the bonding position with LD1 .
- R 141 to R 145 is a single bond that binds to * h1
- the other one of R 141 to R 145 is a single bond that binds to * h2. None of the pairs consisting of two or more adjacent R 141 to R 145 that are not single bonds that bind to * h1 and are not single bonds that bind to * h2 do not bind to each other.
- One or more of the two or more adjacent pairs of R 151 to R 155 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R161 to R165 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 141 to R 145 that are not single bonds that bind to * h1 and are not single bonds that bind to * h2, and the substituted or unsubstituted fused rings that do not form the substituted or unsubstituted monocyclic ring.
- R 151 to R 155 and R 161 to R 165 respectively, independently form a hydrogen atom, an substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming carbon group having 6 to 12 carbon atoms. It is an aryl group and ** represents the bonding position with LD1 . )
- the organic EL element of the present embodiment in the compound represented by the general formula (cHT3-1), the general formula (cHT3-2), the general formula (cHT3-3) and the general formula (cHT3-4).
- the substituent in the case of "substitutable or non-substitutable" is not a group represented by -N ( RC6) (RC7 ) .
- RC6 and RC7 are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, respectively.
- substituent in the case of "substitution or non-substitution" is not a group represented by -N (RC6) ( RC7 ), the above general formulas ( cHT3-1 ), (cHT3-2), (cHT3-)
- the compounds represented by 3) and (cHT3-4) are monoamine compounds.
- the compound contained in the second anode-side organic layer is a diamine having two substituted or unsubstituted amino groups in the molecule. It is a compound.
- the compound contained in the second anode-side organic layer is a triamine compound having three substituted or unsubstituted amino groups in the molecule.
- the compound contained in the second anode-side organic layer is a tetraamine compound having four substituted or unsubstituted amino groups in the molecule.
- the first anode-side organic layer is a compound represented by the general formula (cHT2-1), a compound represented by the general formula (cHT2-2), and a general formula.
- the second anode-side organic layer contains at least one compound selected from the group consisting of the compounds represented by (cHT2-3), and the second anode-side organic layer is a compound represented by the general formula (cHT3-1).
- the compound contained in the second anode-side organic layer may be referred to as a second hole transport band material.
- the second hole transport band material is a compound represented by the general formula (cHT3-1), a compound represented by the general formula (cHT3-2), and a general compound. It is at least one compound selected from the group consisting of a compound represented by the formula (cHT3-3) and a compound represented by the general formula (cHT3-4).
- the second hole transport band material is a monoamine compound, a diamine compound, a triamine compound or a tetraamine compound.
- the hole transport band further includes a third anode-side organic layer, and the third anode-side organic layer includes the second anode-side organic layer and the light emitting region. It is placed in between.
- the second anode-side organic layer and the third anode-side organic layer are in direct contact with each other.
- the third anode-side organic layer and the light emitting region are in direct contact with each other.
- the hole transport band includes only the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer.
- the total film thickness of the hole transport zone corresponds to the total film thickness of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer. ..
- the compound contained in the second anode-side organic layer is different from the compound contained in the third anode-side organic layer.
- the second anode-side organic layer contains one kind of the compound AA
- the third anode-side organic layer is contained. Examples thereof include an embodiment in which the layer contains a kind of compound BB.
- the second anode-side organic layer contains two kinds of compound AA and compound AB
- the third anode-side organic layer contains one kind of compound BB
- compound AA and compound AB are either contained.
- compound BB since it is different from compound BB, it is an embodiment that satisfies the above conditions.
- the second anode-side organic layer contains two kinds of compound AA and compound AB and the third anode-side organic layer contains one kind of compound AB, the second anode with respect to compound AB. Since the side organic layer and the third anode side organic layer contain the same compound, the above conditions are not satisfied.
- the third anode-side organic layer does not contain the compound contained in the first anode-side organic layer.
- the third anode-side organic layer is a compound represented by the general formula (cHT3-1), a compound represented by the general formula (cHT3-2), and a general formula. It contains at least one compound selected from the group consisting of the compound represented by (cHT3-3) and the compound represented by the general formula (cHT3-4).
- the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer have one substituted or unsubstituted amino group in the molecule. Contains monoamine compounds that have only. In one aspect of the organic EL element of the present embodiment, the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer do not contain a diamine compound.
- At least one of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer contains a diamine compound. You can also.
- the compound contained in the third anode-side organic layer may be referred to as a third hole transport band material.
- the third hole transport band material is a compound represented by the general formula (cHT3-1), a compound represented by the general formula (cHT3-2), and the general. It is at least one compound selected from the group consisting of a compound represented by the formula (cHT3-3) and a compound represented by the general formula (cHT3-4).
- the third hole transport band material is a monoamine compound, a diamine compound, a triamine compound or a tetraamine compound.
- the hole transport band further includes a fourth anode-side organic layer, and the fourth anode-side organic layer includes a third anode-side organic layer and a light emitting region. It is placed in between.
- the fourth anode-side organic layer and the light emitting region are in direct contact with each other.
- the fourth anode-side organic layer and the third anode-side organic layer are in direct contact with each other.
- the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer are formed from the anode side. They are arranged in order.
- the fourth anode-side organic layer is a barrier layer.
- the barrier layer transports holes and electrons are arranged on the anode side of the barrier layer. Prevents reaching the organic layer.
- a barrier layer that is in direct contact with the first light emitting layer may be provided so that the excitation energy does not leak from the first light emitting layer to the peripheral layer thereof.
- the barrier layer arranged on the anode side of the first light emitting layer prevents excitons generated in the first light emitting layer from moving to each organic layer in the hole transport zone. It is preferable that the first light emitting layer and the barrier layer are in direct contact with each other.
- the fourth anode-side organic layer contains a fourth hole transport band material.
- the fourth hole transport band material and the third hole transport band material are compounds different from each other.
- the fourth hole transport band material, the third hole transport band material, and the second hole transport band material are compounds different from each other.
- the fourth anode-side organic layer is a compound represented by the general formula (cHT3-1), a compound represented by the general formula (cHT3-2), and a general formula. It contains at least one compound selected from the group consisting of the compound represented by (cHT3-3) and the compound represented by the general formula (cHT3-4).
- the third anode-side organic layer and the fourth anode-side organic layer may both contain the compound represented by the general formula (cHT3-1). It is good, but the molecular structure of the compound contained in the third anode-side organic layer and the compound contained in the fourth anode-side organic layer are different.
- the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer are substituted or unsubstituted. It contains a monoamine compound having only one amino group in the molecule. In one aspect of the organic EL element of the present embodiment, the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer do not contain a diamine compound. ..
- At least one of the first anode-side organic layer, the second anode-side organic layer, the third anode-side organic layer, and the fourth anode-side organic layer. Can also contain diamine compounds.
- the fourth hole transport band material is a compound represented by the general formula (cHT3-1), a compound represented by the general formula (cHT3-2), and a general compound. It is at least one compound selected from the group consisting of a compound represented by the formula (cHT3-3) and a compound represented by the general formula (cHT3-4).
- the fourth hole transport band material is a monoamine compound, a diamine compound, a triamine compound or a tetraamine compound.
- hole transport band materials when the first hole transport band material, the second hole transport band material, the third hole transport band material, and the fourth hole transport band material are referred to as hole transport band materials. There is.
- the hole transport band material according to the present embodiment can be produced by a known method, or can be produced by following the method and using a known alternative reaction and raw material suitable for the target product.
- Specific examples of the hole transport band material according to the present embodiment include the following compounds. However, the present invention is not limited to these specific examples.
- the second organic material (first hole transport band material) contained in the first anode-side organic layer is at least selected from the compound group listed below. It is preferably a kind of compound.
- the compound contained in the second anode-side organic layer is at least one compound selected from the compound group listed below. It is preferable to have.
- the compound contained in the third anode-side organic layer is at least one compound selected from the compound group listed below. It is preferable to have.
- the compound exemplified as the compound contained in any of the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer is shown in duplicate as an example of the other layers.
- the compounds that can be used for the first anode-side organic layer, the second anode-side organic layer, and the third anode-side organic layer are different from each other from the group of compounds exemplified.
- the compound can be appropriately selected.
- Specific examples of the dope compound as the first organic material include the following compounds. However, the present invention is not limited to specific examples of these doped compounds.
- the light emitting region includes at least one light emitting layer.
- the at least one light emitting layer is the first light emitting layer.
- the first light emitting layer contains a first host material.
- the first host material is not particularly limited, but for example, a compound selected from the group consisting of the compound represented by the general formula (H1) described later and the first compound described later can be used.
- the first light emitting layer contains the first light emitting compound.
- the first luminescent compound is not particularly limited, but for example, a compound selected from the group consisting of the compound represented by the general formula (6) described later, the third compound described later, and the fourth compound is used. be able to.
- the first light emitting layer contains a first host material and a first light emitting compound.
- the first luminescent compound is preferably a compound having a maximum peak wavelength of 500 nm or less, and more preferably a compound having a maximum peak wavelength of 430 nm or more and 480 nm or less.
- the first luminescent compound is preferably a fluorescent luminescent compound having a maximum peak wavelength of 500 nm or less, and preferably a fluorescent luminescent compound having a maximum peak wavelength of 430 nm or more and 480 nm or less. More preferred.
- the first light emitting layer contains a first host material and a first light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less.
- the half width of the maximum peak of the first luminescent compound is 1 nm or more and 30 nm or less.
- the first luminescent compound is a compound that does not contain an azine ring structure in the molecule.
- the first luminescent compound is preferably not a boron-containing complex, and more preferably the first luminescent compound is not a complex.
- the fluorescent light emitting compound that fluoresces in blue that can be used for the first light emitting layer
- a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative and the like can be used.
- blue emission refers to emission in which the maximum peak wavelength of the emission spectrum is within the range of 430 nm or more and 500 nm or less.
- the two or more light emitting layers are all fluorescent light emitting layers. That is, in one aspect of the organic EL device of the present embodiment, the light emitting layer included in the light emitting region is a fluorescent light emitting layer. In one aspect of the organic EL device according to the present embodiment, the first light emitting layer does not contain a metal complex. Further, in one aspect of the organic EL device according to the present embodiment, the first light emitting layer does not contain a boron-containing complex.
- the first light emitting layer does not contain a phosphorescent light emitting material (dopant material).
- the first light emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex.
- the heavy metal complex include an iridium complex, an osmium complex, a platinum complex, and the like.
- the method for measuring the maximum peak wavelength of the compound is as follows. A 5 ⁇ mol / L toluene solution of the compound to be measured is prepared, placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K).
- the emission spectrum can be measured by a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd.
- the emission spectrum measuring device is not limited to the device used here.
- the peak wavelength of the emission spectrum having the maximum emission intensity is defined as the maximum peak wavelength.
- the maximum peak wavelength of fluorescence emission may be referred to as the maximum peak wavelength of fluorescence emission (FL-peak).
- the peak having the maximum emission intensity when the peak having the maximum emission intensity is set as the maximum peak and the height of the maximum peak is set to 1, the heights of other peaks appearing in the emission spectrum are 0. It is preferably less than 6.
- the peak in the emission spectrum is a maximum value. Further, it is preferable that the number of peaks is less than 3 in the emission spectrum of the first luminescent compound.
- the first light emitting layer contains the first light emitting compound in an amount of 0.5% by mass or more of the total mass of the first light emitting layer.
- the first light emitting layer preferably contains the first light emitting compound in an amount of 10% by mass or less of the total mass of the first light emitting layer, and preferably contains 7% by mass or less of the total mass of the first light emitting layer. It is more preferable to contain 5% by mass or less of the total mass of the first light emitting layer.
- the "host material” is, for example, a material contained in "50% by mass or more of a layer".
- the first light emitting layer preferably contains the first host material in an amount of 60% by mass or more of the total mass of the first light emitting layer. It is more preferably contained in an amount of 70% by mass or more of the total mass of the light emitting layer, further preferably 80% by mass or more of the total mass of the first light emitting layer, and 90% by mass of the total mass of the first light emitting layer. It is even more preferably contained in an amount of% or more, and even more preferably 95% by mass or more based on the total mass of the first light emitting layer.
- the first light emitting layer preferably contains the first host material in an amount of 99.5% by mass or less based on the total mass of the first light emitting layer.
- the upper limit of the total content of the first host material and the first light emitting compound is 100% by mass. be.
- the organic EL device does not exclude that the first light emitting layer contains a material other than the first host material and the first light emitting compound.
- the first light emitting layer may contain only one kind of the first host material, or may contain two or more kinds.
- the first light emitting layer may contain only one kind of the first light emitting compound, or may contain two or more kinds.
- the first host material has at least one deuterium atom. In one aspect of the organic EL device according to this embodiment, the first host material does not have a deuterium atom.
- the first host material is a compound represented by the following general formula (H1).
- R 301 to R 308 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Substituentally substituted or unsubstituted or unsubstitute
- L 301 and L 302 are independent of each other. Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 301 and Ar 302 are independent of each other. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are independent of each other.
- the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are the same as or different from each other.
- the plurality of R 801s are the same as or different from each other.
- the plurality of R 802s are the same as or different from each other.
- Ar 301 and Ar 302 are independent of each other.
- L 301 is A single-bonded or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms.
- Ar 301 is a substituted or unsubstituted aryl group having 6 to 22 carbon atoms.
- R 301 to R 308 are independent of each other.
- R 301 to R 308 are hydrogen atoms.
- L 302 is a single bond and Ar 302 is an unsubstituted phenyl group. In one aspect of the organic EL device according to this embodiment, L 302 is a single bond and Ar 302 is an unsubstituted 2-naphthyl group. In one aspect of the organic EL device according to this embodiment, L 302 is a single bond and Ar 302 is an unsubstituted 1-naphthyl group.
- L 302 is an unsubstituted p-phenylene group and Ar 302 is an unsubstituted phenyl group. In one aspect of the organic EL device according to the present embodiment, L 302 is an unsubstituted m-phenylene group and Ar 302 is an unsubstituted phenyl group. In one aspect of the organic EL device according to the present embodiment, L 302 is an unsubstituted o-phenylene group and Ar 302 is an unsubstituted phenyl group.
- L 302 is an unsubstituted p-phenylene group and Ar 302 is an unsubstituted 1-naphthyl group. In one aspect of the organic EL device according to the present embodiment, L 302 is an unsubstituted p-phenylene group and Ar 302 is an unsubstituted 2-naphthyl group. In one aspect of the organic EL device according to the present embodiment, L 302 is an unsubstituted 1,4-naphthalenediyl group and Ar 302 is an unsubstituted phenyl group. In one aspect of the organic EL device according to the present embodiment, L 302 is an unsubstituted m-phenylene group and Ar 302 is an unsubstituted 2-naphthyl group.
- R 301 to R 308 each independently have at least one deuterium atom.
- L 301 , L 302 , Ar 301 and Ar 302 each independently have at least one deuterium atom.
- the first host material is a compound represented by the following general formula (H10).
- Ar 301 , R 301 to R 308 , L 301 and L 302 are independently, respectively, in the general formula (H1) Ar 301 , R 301 to R 308 , L 301 and L 302 .
- Is synonymous with X 3 is an oxygen atom or a sulfur atom,
- One or more of the two or more adjacent pairs of the three R 310s Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 310 to R 314 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are independently each of R 901 , in the general formula (H1). Synonymous with R 902 , R 903 , R 904 , R 905 , R 906 and R 907 ).
- one or more sets of two or more adjacent pairs of R 311 to R 314 in the general formula (H10) are bonded to each other and substituted or unsubstituted. Form a benzene ring.
- R 301 to R 308 each independently have at least one deuterium atom.
- L 301 , L 302 , Ar 301 and R 310 to R 314 each independently have at least one deuterium atom.
- the first host material is a compound represented by the following general formula (H31), (H32) or (H33).
- X 3 , R 301 to R 308 , R 310 to R 314 , L 301 , L 302 and Ar 301 are independently expressed in the general formula (H31), (H32) and (H33). It is synonymous with X 3 , R 301 to R 308 , R 310 to R 314 , L 301 , L 302 and Ar 301 in H10).
- R 321 to R 324 are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms,
- the first host material is a compound represented by the following general formula (H301) or (H302).
- X 3 , R 301 to R 308 , R 311 to R 314 , L 301 , L 302 , and Ar 301 are independently X in the general formula (H10).
- R 301 to R 308 , R 311 to R 314 , L 301 , L 302 and Ar 301 are independently X in the general formula (H10).
- R 301 to R 308 , R 311 to R 314 , L 301 , L 302 and Ar 301 are independently X in the general formula (H10).
- R 301 to R 308 , R 311 to R 314 , L 301 , L 302 and Ar 301 are independently X in the general formula (H10).
- One or more of the two or more adjacent pairs of R 315 to R 317 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 315 to R 317 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independent of each other.
- the first host material is a compound represented by the following general formula (H311), (H312), (H321), (H322), (H331) or (H332). Is.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon
- the first host materials L 301 and L 302 are each independently single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 14 carbon atoms. ..
- the first host materials L 301 and L 302 are independently single-bonded, substituted or unsubstituted phenylene groups, or substituted or unsubstituted naphthylene groups, respectively. ..
- the first host materials L 301 and L 302 are single bonds.
- the first host material is a compound represented by the following general formula (H313), (H314), (H323), (H324), (H333) or (H334). Is.
- X3 , R 301 to R 308 , and Ar 301 are independently the general formulas. It is synonymous with X 3 , R 301 to R 308 , and Ar 301 in (H10).
- R 311 to R 317 and R 321 to R 324 are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms,
- the first host materials R 311 to R 317 and R 321 to R 324 are independently, respectively. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- the first host materials R 311 to R 317 and R 321 to R 324 are independently, respectively.
- the first host material Ar 301 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- Ar 301 of the first host material is a group represented by the following general formulas (a1), (a2), (a3) or (a4).
- One or more of the two or more adjacent pairs of R 330 to R 335 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- One or more of the two or more adjacent pairs of R 341 to R 348 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 330 to R 335 and R 341 to R 348 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independent of each other.
- Ar 301 of the first host material is a group represented by the general formula (a1) or (a2).
- the first host materials R 330 to R 335 and R 341 to R 348 are hydrogen atoms.
- X3 of the first host material is an oxygen atom.
- the first host materials R 301 to R 308 are independent of each other.
- the first host materials R 301 to R 308 are independent of each other.
- Hydrogen atom A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.
- R 301 to R 308 of the first host material are hydrogen atoms.
- the first host material is a compound represented by the following general formula (H20).
- R 201 to R 208 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or un
- L 201 , L 202 and L 203 are independently A single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.
- Ar 201 , Ar 202 and Ar 203 are independently substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms.
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are independently described.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 901s the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are present, the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are the same as or different from each other.
- Ar 201 , Ar 202 and Ar 203 are independently phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, diphenylfluorenyl group and dimethyl, respectively. It is a fluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.
- R 201 to R 208 each independently have at least one deuterium atom.
- L 201 , L 202 , L 203 , Ar 201 , Ar 202 and Ar 203 each independently have at least one deuterium atom.
- the compound represented by the general formula (H20) is the following general formula (201), general formula (202), general formula (203), general formula (204). , A compound represented by the general formula (205), the general formula (206), the general formula (207), the general formula (208) or the general formula (209).
- L 201 and Ar 201 are synonymous with L 201 and Ar 201 in the general formula (H20), and R 201 to R 208 are independently said to be general. It is synonymous with R 201 to R 208 in the formula (H20).
- the compound represented by the general formula (H20) is the following general formula (221), general formula (222), general formula (223), general formula (224).
- R 201 and R 203 to R 208 are independently synonymous with R 201 and R 203 to R 208 in the general formula (H20).
- L 201 and Ar 201 are synonymous with L 201 and Ar 201 in the general formula (H20), respectively.
- L 203 is synonymous with L 203 in the general formula (H21).
- L 203 and L 201 are the same as or different from each other.
- Ar 203 is synonymous with Ar 203 in the general formula (H21).
- Ar 203 and Ar 201 are the same as or different from each other.
- the compound represented by the general formula (H20) is the following general formula (241), general formula (242), general formula (243), general formula (244).
- R 201 , R 202 and R 204 to R 208 are independently synonymous with R 201 , R 202 and R 204 to R 208 in the general formula (H20).
- L 201 and Ar 201 are synonymous with L 201 and Ar 201 in the general formula (H20), respectively.
- L 203 is synonymous with L 203 in the general formula (H21).
- L 203 and L 201 are the same as or different from each other.
- Ar 203 is synonymous with Ar 203 in the general formula (H21).
- Ar 203 and Ar 201 are the same as or different from each other.
- R 201 to R 208 are independently hydrogen atoms, substituted or substituted alkyl groups having 1 to 50 carbon atoms, and substituted. Alternatively, it is an unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a group represented by —Si (R 901 ) (R 902 ) (R 903 ).
- L 101 is a single-bonded or unsubstituted arylene group having 6 to 22 carbon atoms, and Ar 101 is substituted. Alternatively, it is an unsubstituted aryl group having 6 to 22 carbon atoms.
- R 201 to R 208 which are substituents of the anthracene skeleton, prevent the interaction between molecules from being suppressed and electron transfer.
- Hydrogen atoms are preferable from the viewpoint of suppressing a decrease in the degree, but R 201 to R 208 are substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, or substituted or unsubstituted ring-forming atoms. It may be a heterocyclic group having the number 5 to 50.
- R 301 to R 308 which are substituents of the anthracene skeleton, prevent the interaction between molecules from being suppressed and suppress the decrease in electron mobility.
- R 301 to R 308 may be an aryl group having 6 to 50 substituted or unsubstituted ring-forming atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. good.
- One aspect of the organic EL device may have an anode, a second light emitting layer, a first light emitting layer, and a cathode in this order, but the first light emitting layer
- the order of the second light emitting layer can also be reversed.
- the stacking order of the first light emitting layer and the second light emitting layer is the order of the second light emitting layer and the first light emitting layer from the anode side, and is included in the first light emitting layer.
- one host material is a compound represented by the general formula (H1)
- the following phenomenon may occur. Therefore, in the general formula (H1), it is preferable that R 301 to R 308 are not bulky substituents.
- the substituents include a haloalkyl group, an alkenyl group, an alkynyl group, a group represented by -Si (R 901 ) (R 902 ) (R 903 ), a group represented by -O- (R 904 ), and-.
- the group represented by S- (R 905 ), the group represented by -N (R 906 ) (R 907 ), the aralkyl group, the group represented by -C ( O) R 801 and the group represented by -COOR 802 .
- the groups to be treated, the halogen atom, the cyano group, and the nitro group may be bulky, and the alkyl group and the cycloalkyl group may be further bulky.
- R 301 to R 308 which are substituents of the anthracene skeleton, are preferably not bulky substituents, preferably not alkyl groups and cycloalkyl groups, and are alkyl.
- Group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, -Si (R 901 ) (R 902 ) (R 903 ) group, -O- (R 904 ) group, -S -A group represented by (R 905 ), a group represented by -N (R 906 ) (R 907 ), an aralkyl group, a group represented by -C ( O) R 801 and a group represented by -COOR 802 . More preferably, it is not a group, a halogen atom, a cyano group, and a nitro group.
- the substituents in the case of "substituted or unsubstituted” in R 301 to R 308 are the above-mentioned substituents that may be bulky, particularly substituted or unsubstituted alkyl groups, and substituents. Alternatively, it is also preferable that it does not contain an unsubstituted cycloalkyl group.
- the substituent in the case of "substituted or unsubstituted" in R 301 to R 308 does not contain a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group, whereby an alkyl group, a cycloalkyl group, etc.
- R 301 to R 308 which are substituents of the anthracene skeleton, are not bulky substituents, and R 301 to R 308 , which are substituents, are unsubstituted. Further, when R 301 to R 308 , which are substituents of the anthracene skeleton, are not bulky substituents, and when the substituents are bonded to R 301 to R 308 , which are not bulky substituents, the substituents are also bulky.
- the groups described as "substituted or unsubstituted” are preferably “unsubstituted” groups.
- the light emitting layer contains a compound represented by the general formula (H10) as a first host material.
- the compound represented by the general formula (H10) has or does not have at least one deuterium atom.
- the light emitting layer contains a compound represented by the general formula (H20) as a first host material.
- the compound represented by the general formula (H20) has or does not have at least one deuterium atom.
- the light emitting layer comprises, as a first host material, a compound represented by the general formula (H10) and a compound represented by the general formula (H20). include. In this embodiment, it is preferable that at least one of the compound represented by the general formula (H10) and the compound represented by the general formula (H20) has at least one deuterium atom.
- the light emitting layer contains, as a first host material, a compound represented by the general formula (H10) and a compound represented by the general formula (H20).
- the compound represented by the general formula (H10) does not substantially contain a deuterium atom
- the compound represented by the general formula (H20) contains at least one deuterium atom.
- the light emitting layer contains, as a first host material, a compound represented by the general formula (H10) and a compound represented by the general formula (H20).
- the compound represented by the general formula (H20) does not substantially contain a deuterium atom
- the compound represented by the general formula (H10) does not contain at least one deuterium atom.
- the compound does not substantially contain a compound having a heavy hydrogen atom means that it does not contain a heavy hydrogen atom at all, or it is permissible to contain a heavy hydrogen atom having a natural abundance ratio. do.
- the natural abundance ratio of deuterium atoms is, for example, 0.015% or less.
- the first host material can be produced by a known method.
- the first host material can also be produced by following a known method and using known alternative reactions and raw materials according to the desired product.
- Specific examples of the first host material include the following compounds. However, the present invention is not limited to specific examples of these first host materials.
- the first luminescent compound is a compound represented by the following general formula (6).
- Ring a, ring b and ring c are independent of each other.
- R 601 and R 602 independently combine with the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
- R601 and R602 which do not form the substituted or unsubstituted heterocycle, are independently of each other.
- Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- the a ring, the b ring and the c ring are rings that are condensed into the fused two-ring structure in the center of the general formula (6) composed of a boron atom and two nitrogen atoms.
- the "aromatic hydrocarbon ring" of the a ring, the b ring and the c ring has the same structure as the compound in which a hydrogen atom is introduced into the "aryl group".
- the "aromatic hydrocarbon ring" of the a ring contains three carbon atoms on the condensed bicyclic structure in the center of the general formula (6) as ring-forming atoms.
- the "aromatic hydrocarbon ring" of the b ring and the c ring contains two carbon atoms on the condensed bicyclic structure in the center of the general formula (6) as ring-forming atoms.
- the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms” include compounds in which a hydrogen atom is introduced into the "aryl group” described in the specific example group G1.
- the "heterocycle” of the a ring, b ring and c ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group”.
- the "heterocycle” of the a ring contains three carbon atoms on the condensed bicyclic structure in the center of the general formula (6) as ring-forming atoms.
- the "heterocycle" of the b ring and the c ring contains two carbon atoms on the condensed bicyclic structure in the center of the general formula (6) as ring-forming atoms.
- Specific examples of the "heterocyclic ring having 5 to 50 substituted or unsubstituted ring-forming atoms” include a compound in which a hydrogen atom is introduced into the "heterocyclic group" described in the specific example group G2.
- R 601 and R 602 may be independently bonded to the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle.
- the heterocycle in this case contains a nitrogen atom on the fused bicyclic structure in the center of the general formula (6).
- the heterocycle in this case may contain a heteroatom other than the nitrogen atom.
- R 601 may be bonded to ring a to form a nitrogen-containing heterocycle in which a ring containing R 601 is condensed with a ring (or a tricyclic condensation or more).
- Specific examples of the nitrogen-containing heterocycle include compounds corresponding to a heterocyclic group having two or more ring condensations containing nitrogen in the specific example group G2. The same applies when R 601 binds to the b ring, R 602 binds to the a ring, and R 602 binds to the c ring.
- R 601 and R 602 may not be independently bonded to the a ring, b ring, or c ring, respectively.
- the a ring, b ring, and c ring in the general formula (6) are independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms. In one embodiment, the a ring, b ring and c ring in the general formula (6) are independently substituted or unsubstituted benzene rings or naphthalene rings, respectively.
- R601 and R602 in the general formula (6) are independent of each other.
- the compound represented by the general formula (6) is a compound represented by the following general formula (62).
- R 601A combines with one or more selected from the group consisting of R 611 and R 621 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R 602A combines with one or more selected from the group consisting of R 613 and R 614 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R 601A and R 602A which do not form the substituted or unsubstituted heterocycle, are independent of each other.
- Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 611 to R 621 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 611 to R 621 which do not form the substituted or unsubstituted heterocycle, do not form the monocycle, and do not form the condensed ring, are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are independently described. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. When there are a plurality of R 901s , the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are present, the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are present, the plurality of R 907s are the same as or different from each other.
- the R 601A and R 602A of the general formula (62) are the groups corresponding to the R 601 and R 602 of the general formula (6), respectively.
- R 601A and R 611 may be bonded to form a nitrogen-containing heterocycle in which a ring containing these and a benzene ring corresponding to the a ring are condensed to form a bicyclic condensation (or a tricyclic condensation or more).
- Specific examples of the nitrogen-containing heterocycle include compounds corresponding to a heterocyclic group having two or more ring condensations containing nitrogen in the specific example group G2. The same applies to the case where R 601A and R 621 are combined, the case where R 602A and R 613 are combined, and the case where R 602A and R 614 are combined.
- R 611 to R 621 may combine with each other to form substituted or unsubstituted monocycles, or they may combine with each other to form substituted or unsubstituted fused rings.
- R 611 and R 612 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed with a 6-membered ring to which they are bonded.
- the formed fused ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.
- R 611 to R 621 which do not contribute to ring formation, are independent of each other.
- R 611 to R 621 which do not contribute to ring formation, are independent of each other.
- Hydrogen atom A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 611 to R 621 which do not contribute to ring formation, are independent of each other. It is a hydrogen atom or an substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- R 611 to R 621 which do not contribute to ring formation, are independent of each other.
- At least one of R 611 to R 621 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- the compound represented by the general formula (62) is a compound represented by the following general formula (63).
- R 631 combines with R 646 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R 633 combines with R 647 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R 634 combines with R 651 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R 641 combines with R 642 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
- R 631 to R 651 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 631 to R 651 which do not form the substituted or unsubstituted heterocycle, do not form the monocyclic ring, and do not form the condensed ring, are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 631 may be combined with R 646 to form a substituted or unsubstituted heterocycle.
- R 631 and R 646 are bonded to form a nitrogen-containing heterocycle having three or more ring condensations in which a benzene ring to which R 646 is bonded, a ring containing N, and a benzene ring corresponding to the a ring are condensed.
- the nitrogen-containing heterocycle include compounds corresponding to a heterocyclic group having three or more ring condensations containing nitrogen in the specific example group G2. The same applies to the case where R 633 and R 647 are combined, the case where R 634 and R 651 are combined, and the case where R 641 and R 642 are combined.
- R 631 to R 651 which do not contribute to ring formation, are independent of each other.
- R 631 to R 651 which do not contribute to ring formation, are independent of each other.
- Hydrogen atom A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 631 to R 651 which do not contribute to ring formation, are independent of each other. It is a hydrogen atom or an substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- R 631 to R 651 which do not contribute to ring formation, are independent of each other.
- At least one of R 631 to R 651 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- the compound represented by the general formula (63) is a compound represented by the following general formula (63A).
- R 661 is Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
- R 662 to R 665 are independent of each other.
- Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
- R 661 to R 665 are independent of each other.
- R 661 to R 665 are independently substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.
- the compound represented by the general formula (63) is a compound represented by the following general formula (63B).
- R 671 and R 672 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- R 673 to R 675 are independent of each other.
- Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an substituted or unsubstituted aryl group having 6 to 50 carbon atoms. )
- the compound represented by the general formula (63) is a compound represented by the following general formula (63B').
- R 672 to R 675 are independently synonymous with R 672 to R 675 in the general formula (63B).
- At least one of R 671 to R 675 is Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- R 672 is Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A group represented by ⁇ N (R 906 ) (R 907 ), or an substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- R 671 and R 673 to R 675 are independent of each other.
- the compound represented by the general formula (63) is a compound represented by the following general formula (63C).
- R 681 and R 682 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
- R 683 to R 686 are independent of each other.
- Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
- the compound represented by the general formula (63) is a compound represented by the following general formula (63C').
- R 683 to R 686 are independently synonymous with R 683 to R 686 in the general formula (63C).
- R 681 to R 686 are independent of each other.
- R 681 to R 686 are independently substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms.
- an intermediate is first formed by binding a ring, b ring and c ring with a linking group (a group containing N-R 601 and a group containing N-R 602 ).
- the final product can be produced by producing (first reaction) and bonding the a ring, b ring and c ring with a linking group (group containing a boron atom) (second reaction).
- first reaction an amination reaction such as the Buchwald-Hartwig reaction can be applied.
- a tandem hetero Friedel-Crafts reaction or the like can be applied.
- the compound represented by the general formula (6) is a compound represented by the following general formula (42-2).
- R 611 to R 617 , R 601A and R 602A are independently synonymous with R 611 to R 617 , R 601A and R 602A in the general formula (62), respectively.
- X4 is an oxygen atom or a sulfur atom
- One or more of the two or more adjacent pairs of R 701 to R 704 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 701 to R 704 which do not form the substituted or unsubstituted monocyclic ring and do not form the condensed ring, are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are independently described as R 901 , R 902 , in the general formula (62), respectively. Synonymous with R 903 , R 904 , R 905 , R 906 and R 907. )
- the light emitting region comprises only the first light emitting layer. In one aspect of the organic EL device of the present embodiment, the light emitting region includes a first light emitting layer and a second light emitting layer. In one aspect of the organic EL device of the present embodiment, the light emitting region comprises only a first light emitting layer and a second light emitting layer.
- the light emitting region has at least a first light emitting layer containing a first host material and a second light emitting layer containing a second host material.
- the first host material and the second host material are different from each other.
- the luminous efficiency can be improved by using Tripret-Triplet-Anhilation (sometimes referred to as TTA).
- TTA is a mechanism in which triplet excitons and triplet excitons collide with each other to generate singlet excitons.
- the TTA mechanism may be referred to as a TTF mechanism as described in International Publication No. 2010/134350.
- the TTF phenomenon will be described.
- the holes injected from the anode and the electrons injected from the cathode recombine in the light emitting layer to generate excitons.
- the spin state has a ratio of 25% for singlet excitons and 75% for triplet excitons, as is conventionally known.
- 25% of singlet excitons emit light when relaxed to the ground state, while the remaining 75% of triplet excitons do not emit light and are thermally deactivated. It returns to the ground state through the process. Therefore, it was said that the theoretical limit value of the internal quantum efficiency of the conventional fluorescent device was 25%.
- the behavior of triplet excitons generated inside organic matter has been theoretically investigated. S. M.
- triplet excitons (hereinafter, triplet excitons).
- 3A * triplet excitons collide with each other and the reaction shown in the following equation occurs.
- 1 A represents the ground state
- 1 A * represents the lowest excited singlet exciton.
- the initially generated singlet is generated.
- the triplet energy T 1 (H1) of the first host material and the triplet energy T 1 (H1) of the second host material is satisfied.
- T 1 (H2) > T 1 (H1) ... (number 1)
- One aspect of the organic EL device according to the present embodiment can improve the luminous efficiency of the device when it has a first light emitting layer and a second light emitting layer satisfying the relationship of the above formula (Equation 1).
- the triplet excitons generated by the recombination of holes and electrons in the second light emitting layer by satisfying the relationship of the above formula (Equation 1) are Even if carriers are excessively present at the interface between the second light emitting layer and the organic layer in direct contact with the second light emitting layer, the triplet excitons existing at the interface between the second light emitting layer and the organic layer are less likely to be quenched. Conceivable. For example, if the recombination region is locally present at the interface between the second light emitting layer and the hole transport layer or the electron barrier layer, quenching due to excess electrons can be considered.
- One aspect of the organic EL element according to the present embodiment is provided with a first light emitting layer and a second light emitting layer so as to satisfy the relationship of the above formula (Equation 1), whereby a triplet generated by the second light emitting layer is provided.
- the term excitons can be prevented from moving to the first light emitting layer without being quenched by the excess carrier, and also suppressing the reverse movement from the first light emitting layer to the second light emitting layer.
- the organic EL element mainly expresses the TTF mechanism by utilizing the second light emitting layer that mainly generates the triplet exciter and the triplet exciter that has moved from the second light emitting layer.
- a compound that comprises one light emitting layer as a different region and has a smaller triplet energy as the first host material in the first light emitting layer than the second host material in the second light emitting layer.
- the first light emitting layer and the second light emitting layer are in direct contact with each other.
- the layer structure in which the first light emitting layer and the second light emitting layer are in direct contact with each other is, for example, any one of the following embodiments (LS1), (LS2) and (LS3). Aspects may also be included.
- (LS1) In the process of evaporating the compound related to the first light emitting layer and the step of evaporating the compound related to the second light emitting layer, there is a region where both the first host material and the second host material coexist. An embodiment in which the region is generated and exists at the interface between the first light emitting layer and the second light emitting layer.
- LS2 When the first light emitting layer and the second light emitting layer contain a light emitting compound, the step of vapor deposition of the compound related to the first light emitting layer and the step of vapor deposition of the compound related to the second light emitting layer are performed.
- LS3 When the first light emitting layer and the second light emitting layer contain a light emitting compound, the step of vapor deposition of the compound related to the first light emitting layer and the step of vapor deposition of the compound related to the second light emitting layer are performed.
- a region made of the luminescent compound, a region made of the first host material, or a region made of the second host material is generated, and the region is the interface between the first light emitting layer and the second light emitting layer.
- the second light emitting layer contains a second host material.
- the second host material is not particularly limited, but for example, a compound selected from the group consisting of the first compound described later and the compound represented by the general formula (H1) can be used.
- the second light emitting layer contains the second light emitting compound.
- the second luminescent compound is not particularly limited, but for example, a compound selected from the group consisting of the compound represented by the general formula (6), the third compound and the fourth compound described later is used. Can be done.
- the second light emitting layer contains a second host material and a second light emitting compound.
- the second luminescent compound and the first luminescent compound contained in the first light emitting layer are compounds that are the same as or different from each other.
- the second host material and the first host material contained in the first light emitting layer are different compounds.
- the second luminescent compound is preferably a compound having a maximum peak wavelength of 500 nm or less, and more preferably a compound having a maximum peak wavelength of 430 nm or more and 480 nm or less.
- the second luminescent compound is preferably a fluorescent luminescent compound having a maximum peak wavelength of 500 nm or less, and preferably a fluorescent luminescent compound having a maximum peak wavelength of 430 nm or more and 480 nm or less. More preferred.
- the second light emitting layer contains a second host material and a second light emitting compound exhibiting light emission having a maximum peak wavelength of 500 nm or less.
- the half width of the maximum peak of the second luminescent compound is 1 nm or more and 30 nm or less.
- the method for measuring the maximum peak wavelength of the compound is as described above.
- the triplet energy T 1 (D1) of the first luminescent compound and the triplet energy T 1 (H1) of the first host material are the following mathematical formulas. It is preferable to satisfy the relationship (Equation 4A). T 1 (D1)> T 1 (H1) ... (number 4A)
- the first luminescent compound and the first host material are produced in the second light emitting layer by satisfying the relationship of the above formula (Equation 4A).
- the triplet excitator is transferred to the first light emitting layer, the energy is transferred to the molecule of the first host material instead of the first luminescent compound having higher triplet energy.
- triplet excitons generated by the recombination of holes and electrons on the first host material do not move to the first luminescent compound with higher triplet energy.
- the triplet excitons generated by recombination on the molecule of the first luminescent compound rapidly transfer energy to the molecule of the first host material.
- the triplet excitons of the first host material do not move to the first luminescent compound, and the triplet excitons efficiently collide with each other on the first host material due to the TTF phenomenon, resulting in singlet excitation. A child is generated.
- the singlet energy S 1 (H1) of the first host material and the singlet energy S 1 (D1) of the first luminescent compound are the following mathematical formulas. It is preferable to satisfy the relationship (Equation 4). S 1 (H1)> S 1 (D1) ... (Equation 4)
- the first luminescent compound and the first host material satisfy the relationship of the above formula (Equation 4), so that the first luminescent compound is singlet. Since the term energy is smaller than the singlet energy of the first host material, the singlet exciter generated by the TTF phenomenon transfers energy from the first host material to the first luminescent compound, and the first emission occurs. Contributes to the luminescence of the sex compound (preferably fluorescent luminescence).
- the stacking order of the first light emitting layer and the second light emitting layer is the order of the second light emitting layer and the first light emitting layer from the anode side.
- the electron mobility ⁇ e (H2) of the second host material and the electron mobility ⁇ e (H1) of the first host material satisfy the relationship of the following formula (Equation 3).
- the first host material and the second host material satisfy the relationship of the following mathematical formula (Equation 3)
- the recombination ability of holes and electrons in the second light emitting layer is improved.
- the stacking order of the first light emitting layer and the second light emitting layer is the order of the second light emitting layer and the first light emitting layer from the anode side.
- the hole mobility ⁇ h (H2) of the second host material and the hole mobility ⁇ h (H1) of the first host material satisfy the relationship of the following mathematical formula (Equation 31). ⁇ h (H2)> ⁇ h (H1) ... (Equation 31)
- the stacking order of the first light emitting layer and the second light emitting layer is the order of the second light emitting layer and the first light emitting layer from the anode side.
- the hole mobility ⁇ h (H2) of the second host material, the electron mobility ⁇ e (H2) of the second host material, the hole mobility ⁇ h (H1) of the first host material, and the first It is also preferable that the electron mobility ⁇ e (H1) of one host material satisfies the relationship of the following formula (Equation 32). ( ⁇ e (H1) / ⁇ h (H1))> ( ⁇ e (H2) / ⁇ h (H2)) ... (Equation 32)
- the singlet energy S 1 (H2) of the second host material and the singlet energy S 1 (D2) of the second luminescent compound are the following mathematical formulas (numbers). It is preferable to satisfy the relationship of 20). S 1 (H2)> S 1 (D2) ... (number 20)
- the singlet exciter generated on the second host material is the second from the second host material. It facilitates energy transfer to the second dopant material and contributes to the emission (preferably fluorescent emission) of the second luminescent compound.
- the triplet energy T 1 (H2) of the second host material and the triplet energy T 1 (D2) of the second luminescent compound are the following mathematical formulas (Equation 20A). It is preferable to satisfy the relationship of. T 1 (D2)> T 1 (H2) ... (number 20A)
- the triplet excitons generated in the second light emitting layer have higher triplet energy. Since it moves on the second host material instead of the second luminescent compound, it is easy to move to the first light emitting layer.
- the second luminescent compound is a compound that does not contain an azine ring structure in the molecule.
- the second luminescent compound is preferably not a boron-containing complex, and more preferably the second luminescent compound is not a complex.
- a blue fluorescent light emitting compound that can be used for the second light emitting layer for example, a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative and the like can be used.
- the second light emitting layer does not contain a metal complex. Further, in one aspect of the organic EL device according to the present embodiment, the second light emitting layer does not contain a boron-containing complex.
- the second light emitting layer does not contain a phosphorescent light emitting material (dopant material). In one aspect of the organic EL element according to the present embodiment, the second light emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex.
- the second light emitting layer contains a light emitting compound in an amount of 0.5% by mass or more of the total mass of the second light emitting layer.
- the second light emitting layer preferably contains a light emitting compound in an amount of 10% by mass or less of the total mass of the second light emitting layer, and preferably 7% by mass or less of the total mass of the second light emitting layer. It is more preferably contained in an amount of 5% by mass or less of the total mass of the second light emitting layer.
- the second light emitting layer preferably contains the second host material in an amount of 60% by mass or more of the total mass of the second light emitting layer, and the second light emitting layer. It is more preferably contained in an amount of 70% by mass or more of the total mass of the light emitting layer, further preferably 80% by mass or more of the total mass of the second light emitting layer, and 90% by mass of the total mass of the second light emitting layer. It is more preferably contained in an amount of% or more, and further preferably contained in an amount of 95% by mass or more based on the total mass of the second light emitting layer.
- the second light emitting layer preferably contains the second host material in an amount of 99.5% by mass or less based on the total mass of the second light emitting layer.
- the upper limit of the total content of the second host material and the second light emitting compound is 100% by mass.
- the organic EL device does not exclude that the second light emitting layer contains a material other than the second host material and the second light emitting compound.
- the second light emitting layer may contain only one kind of the second host material, or may contain two or more kinds.
- the second light emitting layer may contain only one kind of the second light emitting compound, or may contain two or more kinds.
- the film thickness of the first light emitting layer is preferably 5 nm or more, more preferably 15 nm or more.
- the film thickness of the first light emitting layer is 5 nm or more, the triplet excitons that have moved from the second light emitting layer to the first light emitting layer when the light emitting region has the second light emitting layer It is easy to suppress the return to the second light emitting layer again.
- the film thickness of the first light emitting layer is 5 nm or more, triplet excitons can be charged and separated from the recombination portion in the second light emitting layer.
- the film thickness of the first light emitting layer is preferably 20 nm or less.
- the film thickness of the first light emitting layer is 20 nm or less, the density of triplet excitons in the first light emitting layer can be improved to make the TTF phenomenon more likely to occur.
- the film thickness of the first light emitting layer is preferably 5 nm or more and 20 nm or less.
- the film thickness of the second light emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. When the film thickness of the second light emitting layer is 3 nm or more, the film thickness is sufficient to cause the recombination of holes and electrons in the second light emitting layer. In one aspect of the organic EL device according to the present embodiment, the film thickness of the second light emitting layer is preferably 15 nm or less, and more preferably 10 nm or less. When the film thickness of the second light emitting layer is 15 nm or less, the film thickness is sufficiently thin for the triplet excitons to move to the first light emitting layer. In one aspect of the organic EL device according to the present embodiment, the film thickness of the second light emitting layer is more preferably 3 nm or more and 15 nm or less.
- the first host material is, for example, the following general formula (1) in addition to the compound exemplified above (such as the compound represented by the general formula (H1)).
- the compound is selected from the group consisting of the first compound represented by the formula (17X-1), the general formula (17X-2), the general formula (17X-3) and the general formula (18).
- the second host material is, for example, the following general formula (1), general formula (1X), general formula (12X), general formula (13X), general formula ( 14X), general formula (15X), general formula (16X), general formula (1000B), general formula (16X), general formula (17X-1), general formula (17X-2), general formula (17X-3)
- the compound is selected from the group consisting of the first compound represented by the general formula (18) and the compound represented by the general formula (H1). Further, the first compound can also be used as the first host material and the second host material.
- the first compound is a compound represented by the following general formula (1).
- the first compound represented by the following general formula (1) has at least one group represented by the following general formula (11).
- R 101 to R 110 is a group represented by the general formula (11).
- the plurality of groups represented by the general formula (11) are the same or different from each other.
- L 101 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 101 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx is 0, 1, 2, 3, 4 or 5
- the two or more L 101s are the same as or different from each other.
- the two or more Ar 101s are the same as or different from each other. * In the general formula (11) indicates the bonding position with the pyrene ring in the general formula (1).
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are independent of each other.
- the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are the same as or different from each other.
- the plurality of R 801s are the same as or different from each other.
- the plurality of R 802s are the same as or different from each other.
- Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- the Ar 101 is Substituted or unsubstituted phenyl group, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted biphenyl group, Substituted or unsubstituted terphenyl group, Substituted or unsubstituted pyrenyl groups, It is preferably a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted fluorenyl group.
- the first compound is preferably represented by the following general formula (101).
- R 101 to R 120 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -A group represented by
- R 101 to R 110 indicates the connection position with L 101
- one of R 111 to R 120 indicates the connection position with L 101
- L 101 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- mx is 0, 1, 2, 3, 4 or 5 When two or more L 101s are present, the two or more L 101s are the same as or different from each other. )
- L 101 is preferably a single-bonded or substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.
- R 101 to R 110 are groups represented by the general formula (11).
- R 101 to R 110 are groups represented by the general formula (11), and Ar 101 has a substituted or unsubstituted ring-forming carbon number of 6 to 50. It is preferably an aryl group.
- Ar 101 is not a substituted or unsubstituted pyrenyl group
- L 101 is not a substituted or unsubstituted pyrenylene group
- the substituted or unsubstituted aryl group having 6 to 50 carbon atoms as R 101 to R 110 which is not the group represented by the general formula (11), is not a substituted or unsubstituted pyrenyl group.
- R 101 to R 110 which are not groups represented by the general formula (11), are independent of each other.
- R 101 to R 110 which are not groups represented by the general formula (11), are independent of each other.
- Hydrogen atom Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
- R 101 to R 110 which are not the groups represented by the general formula (11), are preferably hydrogen atoms.
- the first compound is a compound represented by the following general formula (1X).
- R 101 to R 112 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -A group represented
- R 101 to R 112 is a group represented by the general formula (11X).
- L 101 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 101 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx is 1, 2, 3, 4 or 5
- the two or more L 101s are the same as or different from each other.
- the two or more Ar 101s are the same as or different from each other. * In the general formula (11X) indicates the bonding position with the benz [a] anthracen ring in the general formula (1X). )
- the group represented by the general formula (11X) is a group represented by the following general formula (111X).
- X 1 is CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 .
- L 111 and L 112 are independent of each other. Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- ma is 1, 2, 3 or 4 mb is 1, 2, 3 or 4 ma + mb is 2, 3 or 4,
- Ar 101 is synonymous with Ar 101 in the general formula (11X).
- R 141 , R 142 , R 143 , R 144 and R 145 are independent of each other.
- L 111 is bonded to the position of the carbon atom of * 2 in the ring structure represented by the general formula (111aX), and L 112 is the general formula (11aX).
- the group represented by the general formula (111X) is represented by the following general formula (111bX).
- X 1 , L 111 , L 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 are independently X 1 , L 111 , L in the general formula (111X). It is synonymous with 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 .
- a plurality of R 141s are the same as or different from each other.
- a plurality of R 142s are the same as or different from each other.
- the group represented by the general formula (111X) is preferably the group represented by the general formula (111bX).
- ma is preferably 1 or 2
- mb is preferably 1 or 2.
- ma is preferably 1 and mb is preferably 1.
- Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- Ar 101 is Substituted or unsubstituted phenyl group, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted biphenyl group, Substituted or unsubstituted terphenyl group, Substituted or unsubstituted benz [a] anthryl group, Substituted or unsubstituted pyrenyl groups, It is preferably a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted fluorenyl group.
- the compound represented by the general formula (1X) is also preferably represented by the following general formula (101X).
- R 111 and R 112 indicates the position of connection with L 101
- one of R 133 and R 134 indicates the position of connection with L 101
- R 101 to R 110 , R 121 to R 130 , R 111 or R 112 not connected to L 101 , and R 133 or R 134 not connected to L 101 are independent of each other.
- L 101 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- mx is 1, 2, 3, 4 or 5 When two or more L 101s are present, the two or more L 101s are the same as or different from each other. )
- L 101 is It is preferably a single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.
- the compound represented by the general formula (1X) is also preferably represented by the following general formula (102X).
- R 111 and R 112 indicates the position of connection with L 111
- one of R 133 and R 134 indicates the position of connection with L 112
- R 101 to R 110 , R 121 to R 130 , R 111 or R 112 not connected to L 111 , and R 133 or R 134 not connected to L 112 are independent of each other.
- X 1 is CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 .
- L 111 and L 112 are independent of each other. Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- ma is 1, 2, 3 or 4 mb is 1, 2, 3 or 4 ma + mb is 2, 3, 4 or 5 and R 141 , R 142 , R 143 , R 144 and R 145 are independent of each other.
- ma in the general formula (102X) is preferably 1 or 2
- mb is preferably 1 or 2.
- ma in the general formula (102X) is preferably 1, and mb is preferably 1.
- the group represented by the general formula (11X) is a group represented by the following general formula (11AX) or a group represented by the following general formula (11BX). Is also preferable.
- R 121 to R 131 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or unsubstituted aralkyl groups having 7
- the plurality of groups represented by the general formula (11AX) are the same or different from each other.
- the plurality of groups represented by the general formula (11BX) are the same or different from each other.
- L 131 and L 132 are independent of each other, Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- the * in the general formula (11AX) and the general formula (11BX) indicates the bonding position with the benz [a] anthracen ring in the general formula (1X), respectively.
- the compound represented by the general formula (1X) is also preferably represented by the following general formula (103X).
- R 101 to R 110 and R 112 are synonymous with R 101 to R 110 and R 112 in the general formula (1X), respectively.
- R 121 to R 131 , L 131 and L 132 are synonymous with R 121 to R 131 , L 131 and L 132 in the general formula (11BX), respectively.
- L 131 is a substituted or unsubstituted arylene group having 6 to 50 carbon atoms.
- L 132 is a substituted or unsubstituted arylene group having 6 to 50 carbon atoms.
- R 101 to R 112 are groups represented by the general formula (11).
- R 101 to R 112 are groups represented by the general formula (11X), and Ar 101 in the general formula (11X) is , Substituted or unsubstituted, ring-forming aryl groups having 6 to 50 carbon atoms are preferable.
- Ar 101 is not a substituted or unsubstituted benz [a] anthryl group
- L 101 is not a substituted or unsubstituted benz [a] anthrylene group
- the substituted or unsubstituted aryl group having 6 to 50 carbon atoms as R 101 to R 110 which is not the group represented by the general formula (11X), is not a substituted or unsubstituted benz [a] anthryl group. It is also preferable.
- R 101 to R 112 which are not groups represented by the general formula (11X), are independently.
- R 101 to R 112 which are not groups represented by the general formula (11X) are Hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms are preferable.
- R 101 to R 112 which are not groups represented by the general formula (11X), are preferably hydrogen atoms.
- the first compound is a compound represented by the following general formula (12X).
- R 1201 to R 1210 Bond to each other to form a substituted or unsubstituted monocycle, or to bond to each other to form a substituted or unsubstituted fused ring.
- R 1201 to R 1210 which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independent of each other.
- the substituent when the substituted or unsubstituted monocycle has a substituent, the substituent when the substituted or unsubstituted fused ring has a substituent, and at least one of R 1201 to R 1210 are present.
- the plurality of groups represented by the general formula (121) are the same or different from each other.
- L 1201 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 1201 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx2 is 0, 1, 2, 3, 4 or 5 and If there are two or more L 1201 , the two or more L 1201s are the same as or different from each other. If there are two or more Ars 1201 , the two or more Ars 1201s are the same as or different from each other.
- * In the general formula (121) indicates the bonding position with the ring represented by the general formula (12X). )
- the pair consisting of two adjacent two of R 1201 to R 1210 is a pair of R 1201 and R 1202 , a pair of R 1202 and R 1203 , and R 1203 and R 1204 .
- the first compound is a compound represented by the following general formula (13X).
- R 1301 to R 1310 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -A group represented by C
- R 1301 to R 1310 is a group represented by the general formula (131).
- the plurality of groups represented by the general formula (131) are the same or different from each other.
- L 1301 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 1301 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx3 is 0, 1, 2, 3, 4 or 5 If there are two or more L 1301 , the two or more L 1301s are the same as or different from each other. If there are two or more Ar 1301 , the two or more Ar 1301s are the same as or different from each other. * In the general formula (131) indicates the bonding position with the fluoranthene ring in the general formula (13X). )
- the two adjacent sets are a set of R 1301 and R 1302 , a set of R 1302 and R 1303 , a set of R 1303 and R 1304 , and R 1304 and R 1305 .
- R 1305 and R 1306 , R 1307 and R 1308 , R 1308 and R 1309 , and R 1309 and R 1310 are bonded to each other.
- the first compound is a compound represented by the following general formula (14X).
- R 1401 to R 1410 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -A
- R 1401 to R 1410 is a group represented by the general formula (141).
- the plurality of groups represented by the general formula (141) are the same or different from each other.
- L 1401 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 1401 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx4 is 0, 1, 2, 3, 4 or 5 and If there are two or more L 1401 , the two or more L 1401s are the same as or different from each other. If there are two or more Ar 1401 , the two or more Ar 1401s are the same as or different from each other. * In the general formula (141) indicates the bonding position with the ring represented by the general formula (14X). )
- the first compound is a compound represented by the following general formula (15X).
- R 1501 to R 1514 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -A group
- R 1501 to R 1514 is a group represented by the general formula (151).
- the plurality of groups represented by the general formula (151) are the same or different from each other.
- L 1501 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 1501 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx5 is 0, 1, 2, 3, 4 or 5 If there are two or more L 1501 , the two or more L 1501s are the same as or different from each other. If there are two or more Ar 1501 , the two or more Ar 1501s are the same as or different from each other. * In the general formula (151) indicates the bonding position with the ring represented by the general formula (15X). )
- the first compound is a compound represented by the following general formula (16X).
- R 1601 to R 1614 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -A group
- R 1601 to R 1614 is a group represented by the general formula (161).
- the plurality of groups represented by the general formula (161) are the same or different from each other.
- L 1601 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 1601 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx6 is 0, 1, 2, 3, 4 or 5 If there are two or more L 1601 , the two or more L 1601s are the same as or different from each other. If there are two or more Ar 1601 , the two or more Ar 1601s are the same as or different from each other. * In the general formula (161) indicates the bonding position with the ring represented by the general formula (16X). )
- the first compound is a compound represented by the following general formula (1000B).
- X is an oxygen atom or a sulfur atom
- R 10 to R 19 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- R 10 to R 19 that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring are independent of each other.
- R 10 to R 19 is a group represented by the general formula (110).
- the plurality of groups represented by the general formula (110) are the same or different from each other.
- L100 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- mx is 1, 2 or 3
- the two or more L 100s are the same as or different from each other.
- Ar 100 is A substituted or unsubstituted aryl group containing three or more rings, or a substituted or unsubstituted heterocyclic group containing two or more aromatic rings and one or more heterocycles. Ar 100 does not contain an anthracene ring and When there are two or more Ar 100s , the two or more Ar 100s are the same as or different from each other. * In the general formula (110) indicates a bonding position. Among the first compounds represented by the general formula (1000B), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- R 901s the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are present, the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are the same as or different from each other.
- the plurality of R 801s are the same as or different from each other.
- the plurality of R 802s are the same as or different from each other.
- X is preferably an oxygen atom.
- the compound represented by the general formula (1000B) preferably has at least one group represented by the general formula (110) and is represented by the following general formula (100).
- R 10 to R 19 are independently synonymous with R 10 to R 19 in the general formula (1000B), and Ar 100 , L 100 and mx are the general formulas (1000B), respectively. It is synonymous with Ar 100 , L 100 and mx in the formula (110).
- the compound represented by the general formula (1000B) is also preferably a compound represented by the following general formula (101) or general formula (102).
- R 10 to R 19 are independently synonymous with R 10 to R 19 in the general formula (1000B), and Ar 100 , L 100 and mx. Is synonymous with Ar 100 , L 100 and mx in the general formula (110), respectively.
- R 10 to R 19 which are not the groups represented by the general formula (110) are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and substituted. Alternatively, it is preferably an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
- R 10 to R 19 which are not the groups represented by the general formula (110) are preferably hydrogen atoms.
- L 100 is preferably an arylene group containing three or less single-bonded or substituted or unsubstituted benzene rings.
- L 100 is not a substituted or unsubstituted anthrylene group.
- L 100 is a single bond.
- the group represented by ⁇ (L 100 ) mx ⁇ in the general formula (110) is a group represented by any of the following general formulas (111) to (120). It is also preferable.
- the group represented by ⁇ (L 100 ) mx ⁇ in the general formula (110) is a group represented by the general formula (111) or (112).
- Ar 100 is preferably an aryl group in which four or more substituted or unsubstituted benzene rings are condensed.
- Ar 100 is preferably an aryl group in which four substituted or unsubstituted benzene rings are condensed, or an aryl group in which five substituted or unsubstituted benzene rings are condensed.
- Ar 100 is represented by the following general formulas (1100), (1200), (1300), (1400), (1500), (1600), (1700) or (1800). It is preferably a group.
- one of R 111 to R 120 is a bond.
- one of R 1201 to R 1212 is a bond.
- one of R 1301 to R 1314 is a bond.
- one of R 1401 to R 1414 is a bond.
- one of R 1501 to R 1514 is a bond.
- one of R 1601 to R 1612 is a bond.
- one of R 1701 to R 1710 is a bond.
- one of R 1801 to R 1812 is a bond.
- R 111 to R 120 that are not bonds, R 1201 to R 1212 that are not bonds, R 1301 to R 1314 that are not bonds, R 1401 to R 1414 that are not bonds, R 1501 to R 1514 that are not bonds, R 1601 to R 1612 , which are not bonds, R 1701 to R 1710 , which are not bonds, and R 1801 to R 1812 , which are not bonds, are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Substituentally substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, -A group
- the group represented by the general formula (1100) is a group represented by the following general formula (1112) when R 111 is a bond, and the group represented by the following general formula (1113) when R 120 is a bond. ), And when R 119 is a bond, it is a group represented by the following general formula (1114).
- R 111 to R 120 are independent of each other. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Substituentally
- R 111 to R 120 which are not bonds, are not bonds.
- R 1201 to R 1212 , non-bonded R 1301 to R 1314 , non-bonded R 1401 to R 1414 , non-bonded R 1501 to R 1514 , non-bonded R 1601 to R 1612 , not bonded R 1701 to R 1710 and R 1801 to R 1812 , which are not bonds, are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and substituted or unsubstituted ring-forming carbon atoms 3 to 3, respectively. It is preferably a cycloalkyl group of 50 or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
- R 111 to R 120 which are not bonds, are not bonds.
- the compound represented by the general formula (1000B) preferably contains only one benzoxanthene ring in the molecule. It is also preferable that the compound has the benzoxanthene ring replaced with the benzothioxanthene ring in the general formula (100), the general formula (101) and the general formula (102).
- the first compound is a compound represented by the following general formula (17X-1).
- X 14 is an oxygen atom or a sulfur atom and
- One or more of the two or more adjacent pairs of R 1401 to R 1404 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- One or more of the two or more adjacent pairs of R 1405 to R 1410 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- At least one of R 1401 to R 1410 is a group represented by the general formula (171-1).
- R 1401 to R 1410 which do not form the monocyclic ring, do not form the condensed ring, and are not the groups represented by the general formula (171-1), are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally substituted or
- R 1401 to R 1410 is a group represented by the general formula (171-1).
- the plurality of groups represented by the general formula (171-1) are the same or different from each other.
- L 1701 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 1701 A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx7 is 0, 1, 2, 3, 4 or 5 and If there are two or more L 1701 , the two or more L 1701s are the same as or different from each other. If there are two or more Ar 1701 , the two or more Ar 1701s are the same as or different from each other.
- R 901 to R 905 , R 801 and R 802 are independently synonymous with R 901 to R 905 , R 801 and R 802 in the general formula (1000B). * In the general formula (171-1) indicates the bonding position with the ring represented by the general formula (17X-1). )
- R 1401 to R 1410 and X 14 are independently synonymous with R 1401 to R 1410 and X 14 in the general formula (17X-1), respectively.
- the group represented by the general formula (171-2) has the same meaning as the group represented by the general formula (171-1), and in the general formula (171-2), L 1701 , Ar 1701 and mx7. Are independently synonymous with L 1701 , Ar 1701 and mx7 in the general formula (171-1).
- the plurality of groups represented by the general formula (171-2) are the same or different from each other. * In the general formula (171-2) indicates the bonding position with the ring represented by the general formula (17X-2).
- R 1401 to R 1410 and X 14 are independently synonymous with R 1401 to R 1410 and X 14 in the general formula (17X-1), respectively.
- the group represented by the general formula (171-3) has the same meaning as the group represented by the general formula (171-1), and in the general formula (171-3), L 1701 , Ar 1701 and mx7. Are independently synonymous with L 1701 , Ar 1701 and mx7 in the general formula (171-1).
- the plurality of groups represented by the general formula (171-3) are the same or different from each other. * In the general formula (171-3) indicates the bonding position with the ring represented by the general formula (17X-3).
- X 14 is preferably an oxygen atom.
- the first compound is a compound represented by the following general formula (18).
- X 18 is an oxygen atom or a sulfur atom and
- One or more of the two or more adjacent pairs of R 1801 to R 1804 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- One or more of two or more adjacent pairs of R 1805 to R 1808 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- At least one of R 1801 to R 1808 is a group represented by the general formula (18X).
- R 1801 to R 1808 which do not form the monocyclic ring, do not form the condensed ring, and are not the groups represented by the general formula (18X), are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), Substituentally
- R 1801 to R 1808 is a group represented by the general formula (18X).
- L 1801 is Single bond, It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
- Ar 1801 is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- mx8 is 0, 1, 2, 3, 4 or 5 If there are two or more L 1801 , the two or more L 1801s are the same as or different from each other. If there are two or more Ar 1801 , the two or more Ar 1801s are the same as or different from each other.
- R 901 to R 905 , R 801 and R 802 are independently synonymous with R 901 to R 905 , R 801 and R 802 in the general formula (1000B). * In the general formula (18X) indicates the bonding position with the ring represented by the general formula (18). )
- X 18 is preferably an oxygen atom.
- the groups described as "substituted or unsubstituted” are preferably “unsubstituted” groups.
- the second host material has a linked structure containing a benzene ring and a naphthalene ring linked by a single bond in the molecule, and the benzene ring and naphthalene in the linked structure.
- the rings are independently further fused or not fused with a monocyclic or fused ring, and the benzene ring and the naphthalene ring in the linked structure are crosslinked at at least one portion other than the single bond. It is also preferable that they are further connected by. Since the second host material has a linking structure including such a crosslink, it can be expected to suppress deterioration of the chromaticity of the organic EL element.
- the second host material in this case has a linked structure (benzene-) containing a benzene ring and a naphthalene ring linked by a single bond as represented by the following formula (X1) or formula (X2) in the molecule. It may be referred to as a naphthalene-linked structure) as the minimum unit, and a monocycle or a fused ring may be further condensed on the benzene ring, or a monocycle or a fused ring may be further condensed on the naphthalene ring. May be condensed.
- the second host material contains, in the molecule, a naphthalene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X3), formula (X4), or formula (X5).
- a naphthalene ring contains a benzene ring, so that it contains a benzene-naphthalene linked structure.
- the cross-linking contains a double bond. That is, it is also preferable that the benzene ring and the naphthalene ring have a structure in which the benzene ring and the naphthalene ring are further linked by a crosslinked structure containing a double bond in a portion other than the single bond.
- the second host material has a biphenyl structure in which the first benzene ring and the second benzene ring are connected by a single bond in the molecule, and the biphenyl structure has a biphenyl structure. It is also preferable that the first benzene ring and the second benzene ring are further linked by cross-linking at at least one portion other than the single bond.
- the first benzene ring and the second benzene ring in the biphenyl structure are further linked by the cross-linking at one portion other than the single bond. Since the second host material has a biphenyl structure including such cross-linking, it can be expected to suppress deterioration of the chromaticity of the organic EL device.
- the cross-linking contains a double bond. In the organic EL device according to the present embodiment, it is also preferable that the cross-linking does not contain a double bond.
- first benzene ring and the second benzene ring in the biphenyl structure are further linked by the cross-linking at two portions other than the single bond.
- the first benzene ring and the second benzene ring in the biphenyl structure are further linked by the cross-linking at two portions other than the single bond, and the cross-linking is doubled. It is also preferable that it does not contain a bond. Since the second host material has a biphenyl structure including such cross-linking, it can be expected to suppress deterioration of the chromaticity of the organic EL device.
- the biphenyl structure becomes It has a linked structure (condensed ring) such as the following formulas (BP11) to (BP15).
- the formula (BP11) is a structure in which one portion other than the single bond is linked by a crosslink that does not contain a double bond.
- the formula (BP12) is a structure in which one portion other than the single bond is linked by a crosslink containing a double bond.
- the formula (BP13) is a structure in which two portions other than the single bond are linked by a crosslink that does not contain a double bond.
- the formula (BP14) has a structure in which one of the two portions other than the single bond is linked by a cross-link containing no double bond, and the other of the two portions other than the single bond is linked by a cross-link containing a double bond. Is.
- the formula (BP15) is a structure in which two portions other than the single bond are linked by a crosslink containing a double bond.
- the groups described as "substituted or unsubstituted” are preferably “unsubstituted” groups.
- the first compound that can be used in the organic EL device according to the present embodiment can be produced by a known method.
- the first compound can also be produced by following a known method and using known alternative reactions and raw materials suitable for the desired product.
- Specific examples of the first compound that can be used in the organic EL device according to the present embodiment include the following compounds. However, the present invention is not limited to specific examples of these first compounds.
- D represents a deuterium atom
- Me represents a methyl group
- tBu represents a tert-butyl group.
- the first luminescent compound and the second luminescent compound include compounds other than the compounds exemplified above (compounds represented by the general formula (6) and the like).
- the following third compound, the following fourth compound, and the like can be mentioned.
- the third compound and the fourth compound are independently represented by the following general formula (3), the following general formula (4), and the following general formula (5).
- R 301 to R 310 Combine with each other to form substituted or unsubstituted monocycles, Bond to each other to form substituted or unsubstituted fused rings, or do not bond to each other.
- At least one of R 301 to R 310 is a monovalent group represented by the following general formula (31).
- R 301 to R 310 which do not form the monocyclic ring, do not form the condensed ring, and are not monovalent groups represented by the following general formula (31), are independent of each other.
- Hydrogen atom Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -A group represented by Si (R 901 ) (R 902 ) (R 903 ), A group represented by -O- (R 904 ), A group represented by -S- (R 905 ), -A group represented by N (R 906 ) (R 907 ), Halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- Ar 301 and Ar 302 are independent of each other.
- L 301 to L 303 are independent of each other, Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms. * Indicates the bond position in the pyrene ring in the general formula (3).
- R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 are independently. Hydrogen atom, Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
- the plurality of R 901s are the same as or different from each other.
- the plurality of R 902s are the same as or different from each other.
- the plurality of R 903s are the same as or different from each other.
- the plurality of R 904s are the same as or different from each other.
- the plurality of R 905s are the same as or different from each other.
- the plurality of R- 906s are present, the plurality of R- 906s are the same as or different from each other.
- the plurality of R 907s are present, the same as or different from each other.
- R 301 to R 310 are groups represented by the general formula (31).
- the compound represented by the general formula (3) is a compound represented by the following general formula (33).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Theoretical Computer Science (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
La présente invention concerne un élément électroluminescent organique (1) comprenant une région électroluminescente (5) disposée entre une électrode négative (4) et une électrode positive (3), une première couche organique côté électrode positive (61) et une seconde couche organique côté électrode positive (62). La région électroluminescente (5) comprend au moins une première couche électroluminescente (51). La première couche organique côté électrode positive est en contact direct avec la seconde couche organique côté électrode positive. La première couche organique côté électrode positive (61) contient un premier matériau organique et un second matériau organique. La première teneur en matériau organique de la première couche organique côté électrode positive (61) est inférieure à 50 % en masse. La seconde couche organique côté électrode positive contient un second matériau de zone de transport de trous. La première couche électroluminescente (51) est une couche électroluminescente fluorescente. L'indice de réfraction NM1 d'un matériau constituant contenu dans la première couche organique côté électrode positive (61) et l'indice de réfraction NM2 d'un matériau constituant contenu dans la seconde couche organique côté électrode positive (62) satisfont la relation d'expression numérique (expression numérique NM). Expression numérique NM : NM1>NM2
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18/259,254 US20240130224A1 (en) | 2020-12-25 | 2021-12-24 | Organic electroluminescent element and electronic device |
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020-217949 | 2020-12-25 | ||
JP2020217949 | 2020-12-25 | ||
JP2021074498 | 2021-04-26 | ||
JP2021-074498 | 2021-04-26 | ||
JP2021106108 | 2021-06-25 | ||
JP2021-106127 | 2021-06-25 | ||
JP2021106127 | 2021-06-25 | ||
JP2021-106108 | 2021-06-25 | ||
JP2021-163146 | 2021-10-01 | ||
JP2021163146 | 2021-10-01 | ||
US17/511,495 US11575087B1 (en) | 2020-12-25 | 2021-10-26 | Organic electroluminescence device, light emitting device, organic electroluminescence display device and electronic device |
US17/511,495 | 2021-10-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022138950A1 true WO2022138950A1 (fr) | 2022-06-30 |
Family
ID=82158271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2021/048350 WO2022138950A1 (fr) | 2020-12-25 | 2021-12-24 | Élément électroluminescent organique et dispositif électronique |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2022138950A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20220216407A1 (en) * | 2020-12-28 | 2022-07-07 | Lg Display Co., Ltd. | Organic Light Emitting Device |
WO2023054678A1 (fr) * | 2021-10-01 | 2023-04-06 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011054668A (ja) * | 2009-08-31 | 2011-03-17 | Panasonic Electric Works Co Ltd | 有機電界発光素子 |
WO2017138526A1 (fr) * | 2016-02-10 | 2017-08-17 | 学校法人関西学院 | Élément électroluminescent à champ électrique organique à fluorescence retardée |
WO2019198806A1 (fr) * | 2018-04-13 | 2019-10-17 | 出光興産株式会社 | Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique |
WO2019235475A1 (fr) * | 2018-06-04 | 2019-12-12 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique |
WO2020080417A1 (fr) * | 2018-10-16 | 2020-04-23 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique |
KR20200129989A (ko) * | 2019-05-10 | 2020-11-18 | 주식회사 엘지화학 | 유기 발광 소자 |
-
2021
- 2021-12-24 WO PCT/JP2021/048350 patent/WO2022138950A1/fr active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011054668A (ja) * | 2009-08-31 | 2011-03-17 | Panasonic Electric Works Co Ltd | 有機電界発光素子 |
WO2017138526A1 (fr) * | 2016-02-10 | 2017-08-17 | 学校法人関西学院 | Élément électroluminescent à champ électrique organique à fluorescence retardée |
WO2019198806A1 (fr) * | 2018-04-13 | 2019-10-17 | 出光興産株式会社 | Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique |
WO2019235475A1 (fr) * | 2018-06-04 | 2019-12-12 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique |
WO2020080417A1 (fr) * | 2018-10-16 | 2020-04-23 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique |
KR20200129989A (ko) * | 2019-05-10 | 2020-11-18 | 주식회사 엘지화학 | 유기 발광 소자 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20220216407A1 (en) * | 2020-12-28 | 2022-07-07 | Lg Display Co., Ltd. | Organic Light Emitting Device |
WO2023054678A1 (fr) * | 2021-10-01 | 2023-04-06 | 出光興産株式会社 | Élément électroluminescent organique et dispositif électronique |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2021049653A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2021090932A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
KR20190000936A (ko) | 발광 소자 | |
WO2021210582A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2021132535A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2021162057A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2021256564A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2022138950A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2021090930A1 (fr) | Élément électroluminescent organique et équipement électronique | |
WO2021049655A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2022154029A1 (fr) | Élément électroluminescent organique, dispositif d'affichage électroluminescent organique et dispositif électronique | |
WO2021090931A1 (fr) | Dispositif d'affichage électroluminescent organique, et appareil électronique | |
WO2021049663A1 (fr) | Élément électroluminescent organique et appareil électronique | |
WO2022154030A1 (fr) | Élément électroluminescent organique, appareil d'affichage électroluminescent organique et dispositif numérique | |
WO2022230844A1 (fr) | Élément électroluminescent organique, appareil d'affichage électroluminescent organique et dispositif électronique | |
WO2022114156A1 (fr) | Élément électroluminescent organique, appareil d'émission de lumière électroluminescente organique et dispositif électronique | |
WO2021049661A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2021049656A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2022138948A1 (fr) | Élément électroluminescent organique, dispositif émettant de la lumière, dispositif d'affichage électroluminescent organique et dispositif électronique | |
WO2023054678A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2022138949A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2023054679A1 (fr) | Élément électroluminescent organique, dispositif d'affichage électroluminescent organique et équipement électronique | |
WO2021256565A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2023063402A1 (fr) | Élément électroluminescent organique et dispositif électronique | |
WO2022118867A1 (fr) | Élément électroluminescent organique et dispositif électronique |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21911087 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 18259254 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 21911087 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: JP |