WO2018110497A1 - 多環芳香族アミノ化合物 - Google Patents
多環芳香族アミノ化合物 Download PDFInfo
- Publication number
- WO2018110497A1 WO2018110497A1 PCT/JP2017/044361 JP2017044361W WO2018110497A1 WO 2018110497 A1 WO2018110497 A1 WO 2018110497A1 JP 2017044361 W JP2017044361 W JP 2017044361W WO 2018110497 A1 WO2018110497 A1 WO 2018110497A1
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- WIPO (PCT)
- Prior art keywords
- aryl
- alkyl
- heteroaryl
- carbon atoms
- organic
- Prior art date
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- -1 Polycyclic aromatic amino compound Chemical class 0.000 title claims description 189
- 150000001875 compounds Chemical class 0.000 claims abstract description 163
- 239000000463 material Substances 0.000 claims abstract description 163
- 125000003118 aryl group Chemical group 0.000 claims abstract description 123
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 238000002347 injection Methods 0.000 claims description 88
- 239000007924 injection Substances 0.000 claims description 88
- 125000001072 heteroaryl group Chemical group 0.000 claims description 87
- 125000004432 carbon atom Chemical group C* 0.000 claims description 70
- 238000005401 electroluminescence Methods 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 59
- 230000005525 hole transport Effects 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 239000010409 thin film Substances 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000004986 diarylamino group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 10
- 150000002910 rare earth metals Chemical class 0.000 claims description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 230000005669 field effect Effects 0.000 claims description 9
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 8
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 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 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052805 deuterium Chemical group 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 10
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 286
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 230000032258 transport Effects 0.000 description 66
- 229910052757 nitrogen Inorganic materials 0.000 description 65
- 239000002019 doping agent Substances 0.000 description 55
- 239000000758 substrate Substances 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000010408 film Substances 0.000 description 33
- 229910052751 metal Inorganic materials 0.000 description 30
- 239000002184 metal Substances 0.000 description 30
- 229910052782 aluminium Inorganic materials 0.000 description 27
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 26
- 125000001424 substituent group Chemical group 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 238000000151 deposition Methods 0.000 description 18
- 230000008021 deposition Effects 0.000 description 18
- 239000003480 eluent Substances 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 238000007740 vapor deposition Methods 0.000 description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 15
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 15
- 229910052749 magnesium Inorganic materials 0.000 description 15
- 229910052709 silver Inorganic materials 0.000 description 15
- 239000004332 silver Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000011521 glass Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000004065 semiconductor Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000003107 substituted aryl group Chemical group 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 229910052796 boron Inorganic materials 0.000 description 10
- 230000005284 excitation Effects 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 10
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 10
- 239000004926 polymethyl methacrylate Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000006862 quantum yield reaction Methods 0.000 description 10
- 229910052792 caesium Inorganic materials 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 150000004775 coumarins Chemical class 0.000 description 7
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- HVQYTVWOXZCHLC-UHFFFAOYSA-N C1=C(N(C2=C3C(=CC(=C2)O)C=CC=C3)C2=CC=CC=C2)C=CC=C1 Chemical compound C1=C(N(C2=C3C(=CC(=C2)O)C=CC=C3)C2=CC=CC=C2)C=CC=C1 HVQYTVWOXZCHLC-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 239000003341 Bronsted base Substances 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 150000001556 benzimidazoles Chemical class 0.000 description 5
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 230000005281 excited state Effects 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 238000007122 ortho-metalation reaction Methods 0.000 description 5
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012212 insulator Substances 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 150000002790 naphthalenes Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 150000004880 oxines Chemical class 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 150000005041 phenanthrolines Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 3
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000007336 electrophilic substitution reaction Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
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- KQXGBNZZUYDUSG-UHFFFAOYSA-N n,n-diphenyl-4-[4-[4-[4-(n-phenylanilino)naphthalen-1-yl]phenyl]phenyl]naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(N(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)=CC=1)C1=CC=CC=C1 KQXGBNZZUYDUSG-UHFFFAOYSA-N 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004225 phenalen-1-yl group Chemical group [H]C1=C([H])C2=C3C(C([H])=C([H])C([H])(*)C3=C([H])C([H])=C2[H])=C1[H] 0.000 description 1
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- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
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- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001486 pyren-4-yl group Chemical group [H]C1=C(C2=C34)C([H])=C([H])C([H])=C2C([*])=C([H])C3=C([H])C([H])=C([H])C4=C1[H] 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000004322 quinolinols Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000002887 superconductor Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical class 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- WGWZJNILGYTDHU-UHFFFAOYSA-K tris(3,5-dimethylphenoxy)alumane Chemical compound CC=1C=C([O-])C=C(C1)C.[Al+3].CC=1C=C([O-])C=C(C1)C.CC=1C=C([O-])C=C(C1)C WGWZJNILGYTDHU-UHFFFAOYSA-K 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- 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]
- H10K50/17—Carrier injection layers
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- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a polycyclic aromatic amino compound, an organic electroluminescence device using the same, an organic field effect transistor, an organic thin film solar cell, a display device, and a lighting device.
- the organic EL element has a structure composed of a pair of electrodes composed of an anode and a cathode, and one layer or a plurality of layers including an organic compound disposed between the pair of electrodes.
- the layer containing an organic compound include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons.
- Various organic materials suitable for these layers have been developed.
- a benzofluorene compound has been developed (International Publication No. 2004/061047).
- a hole transport material for example, a triphenylamine compound has been developed (Japanese Patent Laid-Open No. 2001-172232).
- an anthracene compound has been developed (Japanese Patent Laid-Open No. 2005-170911).
- the charge transport property of a NO-linked compound (Compound 1 on page 63) is evaluated, but a method for producing a material other than the NO-linked compound is not described, and the element to be linked is not described. Since the electronic state of the entire compound is different if it is different, the characteristics obtained from materials other than NO-linked compounds are not yet known. Other examples of such compounds can also be found (WO 2011/107186, WO 2015/102118).
- a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence having a shorter wavelength, and thus is useful as a blue light-emitting layer material.
- a compound having a novel conjugated structure having a large T1 is also required as an electron transport material or a hole transport material sandwiching the light emitting layer.
- the host material of the organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene and carbazole are connected by a single bond, phosphorus atom or silicon atom. This is because a large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material is secured by connecting a large number of relatively conjugated aromatic rings. Furthermore, a host material of an organic EL device using a phosphorescent material or a thermally activated delayed fluorescent material also requires high triplet excitation energy (E T ), but the molecule has a donor or acceptor aromatic ring or substituent.
- E T triplet excitation energy
- the present inventors have found a novel polycyclic aromatic amino compound having an amino substituent and connecting a plurality of aromatic rings with a boron atom and an oxygen atom, The production was successful.
- the present inventors have found that an excellent organic EL device can be obtained by arranging an organic EL device by arranging a layer containing this polycyclic aromatic amino compound between a pair of electrodes, thereby completing the present invention. That is, this invention provides the organic EL element material containing the following polycyclic aromatic amino compounds and also the following polycyclic aromatic amino compounds.
- Item 1 The polycyclic aromatic amino compound represented by the following general formula (1A) or general formula (1B).
- Each Ar is independently aryl or heteroaryl;
- R 1 to R 4 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy, trialkylsilyl, aryloxy or cyano,
- One hydrogen may be substituted with aryl, heteroaryl, diarylamino or alkyl;
- Each Ar is independently aryl;
- R 2 to R 4 are each independently hydrogen, aryl, heteroaryl, diarylamino, alkyl, alkoxy, trialkylsilyl or aryloxy, in which at least one hydrogen is substituted with aryl, heteroaryl or alkyl May have been
- R 4 is a plurality, at least one hydrogen of the aryl in adjacent R 4 together may form an aryl or heteroaryl ring with a ring attached, the ring formed, heteroaryl, alkyl, Optionally substituted with alkoxy, trialkylsilyl or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl or alkyl
- m is an integer of 0 to 3
- n is each independently an integer from 0 to the maximum possible number of substitution with Ar
- p is an integer of 0 to 4
- q is 0,
- X 1 and X 2 are each independently O or N—R, wherein R in N—R is
- R 2 to R 4 are each independently hydrogen, aryl, heteroaryl, diarylamino, alkyl, alkoxy, trialkylsilyl or aryloxy, in which at least one hydrogen is substituted with aryl, heteroaryl or alkyl May have been
- R 4 is a plurality, at least one hydrogen of the aryl in adjacent R 4 together may form an aryl or heteroaryl ring with a ring attached, the ring formed, heteroaryl, alkyl, Optionally substituted with alkoxy, trialkylsilyl or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl or alkyl;
- m is an integer of 0 to 3
- n is each independently an integer of 0 to 5
- p is an integer of 0 to 4
- Item 4 The polycyclic aromatic amino compound according to item 1, represented by the following general formula (1A ′).
- R 2 and R 3 are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino having 6 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms, carbon number 1 to 24 alkoxy, trialkylsilyl having 1 to 4 carbon atoms or aryloxy having 6 to 30 carbon atoms, wherein at least one hydrogen is aryl having 6 to 16 carbon atoms, 2 to 25 carbon atoms Which may be substituted with heteroaryl or alkyl having 1 to 18 carbon atoms, m is an integer from 0 to 3, n is each independently an integer from 0 to 5, X 1 and X 2 are each independently O or N—R, wherein R in the N—R is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, or 1 to 4 carbon
- R 2 and R 3 each independently represent hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms or alkyl having 1 to 4 carbon atoms.
- Cyril, m is 0 or 1
- n is independently 0 or 1
- X 1 and X 2 are each independently O or N—R, wherein R in the N—R is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, or 1 to 4 carbon atoms Is alkyl, Item 5.
- Item 6. The polycyclic aromatic amino compound according to item 1, represented by the following formula (1A-1), formula (1A-153), formula (1A-173), or formula (1B-92).
- Item 7 An organic device material comprising the polycyclic aromatic amino compound according to any one of Items 1 to 6.
- Item 8 The organic device material according to Item 7, wherein the organic device material is an organic electroluminescent element material, an organic field effect transistor material, or an organic thin film solar cell material.
- Item 9 The material for an organic electroluminescent element according to Item 8, which is a material for a light emitting layer.
- Item 10 The organic electroluminescent element material according to Item 8, which is an electron injection layer material or an electron transport layer material.
- Item 11 The organic electroluminescent element material according to Item 8, which is a hole injection layer material or a hole transport layer material.
- An organic electroluminescence device comprising: a pair of electrodes composed of an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes and containing the light-emitting layer material described in Item 9.
- Item 13 The electron injection layer material and / or electron transport according to Item 10, disposed between the pair of electrodes composed of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, and the cathode and the light emitting layer.
- An organic electroluminescence device having an electron injection layer and / or an electron transport layer containing a layer material.
- Item 14 A hole injection layer material and / or a positive electrode disposed between a pair of electrodes composed of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, and the anode and the light emitting layer.
- An organic electroluminescence device having a hole injection layer and / or a hole transport layer containing a hole transport layer material.
- Item 15 An electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer is a quinolinol-based metal complex, a pyridine derivative, or a phenanthroline derivative; Item 15.
- the electron transport layer and / or the electron injection layer further includes an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, or an alkaline earth metal.
- Item 15 contains at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes.
- Item 17 A display device comprising the organic electroluminescent element according to any one of Items 12 to 16.
- Item 18. A lighting device comprising the organic electroluminescent element according to any one of Items 12 to 16.
- a novel polycyclic aromatic amino compound that can be used for example, as a material for an organic EL device can be provided, and an excellent organic material can be obtained by using this polycyclic aromatic amino compound.
- An EL element can be provided.
- a polycyclic aromatic amino compound having an amino substituent and having an aromatic ring connected by a hetero element such as boron, oxygen, or nitrogen has a large HOMO-LUMO gap (in a thin film). It has been found that it has a band gap Eg) and a high triplet excitation energy (E T ). This is because a 6-membered ring containing a hetero element has low aromaticity, so that the reduction of the HOMO-LUMO gap accompanying expansion of the conjugated system is suppressed, and the triplet excited state (T1) is caused by electronic perturbation of the hetero element. ) SOMO1 and SOMO2 are considered to be localized.
- the polycyclic aromatic amino compound containing a hetero element according to the present invention has a triplet because the interaction between both orbitals becomes small due to localization of SOMO1 and SOMO2 in the triplet excited state (T1). Since the energy difference between the excited state (T1) and the singlet excited state (S1) is small and shows thermally activated delayed fluorescence, it is also useful as a fluorescent material for organic EL elements. A material having a high triplet excitation energy (E T ) is also useful as an electron transport layer or a hole transport layer of a phosphorescent organic EL device or an organic EL device using thermally activated delayed fluorescence. Furthermore, since these polycyclic aromatic amino compounds can move the energy of HOMO and LUMO arbitrarily by introducing substituents, it is possible to optimize the ionization potential and electron affinity according to the surrounding materials. is there.
- polycyclic aromatic amino compound The present invention is a polycyclic aromatic amino compound represented by the following general formula (1A) or general formula (1B).
- the present invention is preferably a polycyclic aromatic amino compound represented by the following general formula (1A ′) or general formula (1B ′).
- Ar is limited to a phenyl group, and substituents of R 1 to R 4 and the numbers m, n, p, and q are appropriately limited.
- Ar is each independently aryl or heteroaryl.
- aryl examples include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.
- aryls include: monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), condensed Examples include tricyclic acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, fused tetracyclic triphenylenyl, pyrenyl, naphthacenyl, fused pentacyclic perylenyl, pentacenyl, and the like.
- heteroaryl examples include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, and heteroaryl having 2 to 15 carbon atoms. Is more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable.
- heteroaryl examples include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
- heteroaryl examples include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phen
- R 1 to R 4 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy, trialkylsilyl, aryloxy or cyano, One hydrogen may be substituted with aryl, heteroaryl, diarylamino or alkyl.
- Diarylamino, diheteroarylamino and arylheteroarylamino as R 1 to R 4 are groups in which an amino group is substituted with two aryl groups, two heteroaryl groups, one aryl group and one heteroaryl group, respectively. And aryl and heteroaryl here can also refer to the explanation of Ar above.
- the alkyl as R 1 to R 4 may be linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms.
- Alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons) is preferable, alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons) is more preferable, and alkyl having 1 to 6 carbons. (Branched alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferable.
- alkyl examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, and 1-methyl.
- Pentyl 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propyl Pentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n- Tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-hepta Sill, n- octadecyl, such as n- eicosyl, and the like
- alkoxy as R 1 to R 4 examples include straight-chain alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms.
- C1-C18 alkoxy (C3-C18 branched alkoxy) is preferred, C1-C12 alkoxy (C3-C12 branched alkoxy) is more preferred, and C1-C6 Of alkoxy (C3-C6 branched chain alkoxy) is more preferable, and C1-C4 alkoxy (C3-C4 branched chain alkoxy) is particularly preferable.
- alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.
- Examples of the trialkylsilyl as R 1 to R 4 include those in which three hydrogens in the silyl group are each independently substituted with alkyl, and the alkyl is as described in the column of alkyl as R 1 to R 4 Is given.
- Preferable alkyl for substitution is alkyl having 1 to 4 carbon atoms, and specific examples include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl and the like.
- trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl , Butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropyl Silyl, ethyldipropylsilyl, butyldipropylsilyl, sec-buty
- Aryloxy as R 1 to R 4 is a group in which a hydrogen atom of a hydroxyl group is substituted with aryl, and the aryl here can refer to the explanation of Ar.
- At least one hydrogen in R 1 to R 4 may be substituted with aryl, heteroaryl, diarylamino or alkyl, and the above description can be cited for these substituents.
- R 4 in General Formula (1B) and General Formula (1B ′) is plural, adjacent R 4 may be bonded to each other to form an aryl ring or a heteroaryl ring together with a ring.
- At least one hydrogen in the ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy, trialkylsilyl, aryloxy or cyano, at least one of which Hydrogen may be substituted with aryl, heteroaryl, diarylamino or alkyl.
- the case where the substituent R 4 is adjacent means a case where two substituents R 4 are substituted on adjacent carbons on the a ring (benzene ring).
- the polycyclic aromatic amino compound represented by the general formula (1B) or the general formula (1B ′) is represented by the following general formula (1B-a ′) and the general formula depending on the mutual bonding form of the substituents in the a ring. As shown in (1B′-a ′), the ring structure constituting the compound changes (a ring changes to a ′ ring).
- the compounds represented by the general formula (1B-a ′) and the general formula (1B′-a ′) are listed as specific compounds described later, for example, the formula (1B-21) to the formula (1B-36), It corresponds to a compound represented by formula (1B-41), formula (1B-42) or formula (1B-46). That is, it is a compound having an a ′ ring formed by condensation of a benzene ring or the like with a benzene ring which is a ring, and the condensed ring a ′ formed is a naphthalene ring or the like.
- a carbazole ring formed by condensation of an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring with a benzene ring that is a ring (the hydrogen on N is substituted with the above alkyl or aryl).
- an indole ring including those in which the hydrogen on N is substituted with the above alkyl or aryl
- a dibenzofuran ring or a dibenzothiophene ring is included indole ring.
- R 1 and R 3 in the general formulas (1A) and (1B) are adjacent to each other, they may be bonded by —O—, —S—, —C (—R) 2 —, or a single bond R of —C (—R) 2 — is hydrogen or alkyl having 1 to 6 carbons (particularly alkyl having 1 to 4 carbons (eg, methyl, ethyl, etc.)).
- R 1 and R 3 are adjacent to each other, for example, as described below, the substituent R 3 is substituted next to the bonding position with N (nitrogen) in Ar (phenyl), and N (nitrogen) in the naphthalene structure
- the substituent R 1 is substituted next to the bonding position (position 1) of (position 2 or position 8).
- the two substituents may be combined as described above.
- n is an integer from 0 to the maximum possible number of substitution with Ar
- p is an integer of 0 to 4
- q is independently of 0 to 5 Is an integer.
- M is preferably an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 0.
- Each n is independently preferably an integer of 0 to 5, more preferably an integer of 0 to 3, particularly preferably an integer of 0 to 2, further preferably 0 or 1.
- Most preferably 0. p is preferably an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 0.
- Each q is independently preferably 0 to 2, particularly preferably 0 or 1, and more preferably 0.
- X 1 and X 2 are each independently O or N—R, wherein R in N—R is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, or 1 to 6 carbons Alkyl.
- R in the general formulas (1B) and (1B ′) is N—R
- R is —O—, —S—, —C (—R) 2 —, or a single bond to the ring a.
- R in —C (—R) 2 — may be bonded to hydrogen or alkyl having 1 to 6 carbons (particularly alkyl having 1 to 4 carbons (eg, methyl, ethyl, etc.)).
- R 1 to R 4 can also be cited for the alkyl as —R in —C (—R) 2 —.
- R in N—R is bonded to the a ring by —O—, —S—, —C (—R) 2 — or a single bond” is defined by the following general formula (1B-a Or a compound having a ring structure in which X 2 is incorporated into a condensed ring a ′′, represented by general formula (1B′-a ′′).
- the condensed ring a ′′ thus formed is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
- At least one hydrogen in the compound represented by the general formula (1A) or the general formula (1B) may be substituted with halogen or deuterium.
- Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine, more preferably fluorine.
- polycyclic aromatic amino compound according to the present invention can be used as a material for organic devices.
- an organic device an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, etc. are mention
- a compound in which X 1 is NR and X 2 is O is preferable, and a compound in which X 1 is O and X 2 is NR as a host material of the light emitting layer, X 1 is NR , A compound in which X 2 is O, and a compound in which X 1 and X 2 are O are preferable, and a compound in which X 1 and X 2 are O is preferably used as an electron transport material.
- polycyclic aromatic amino compound of the present invention examples include, for example, compounds represented by the following formulas (1A-1) to (1A-286), and formulas (1B-1) to (1A) -226), and compounds represented by the following formulas (1B-231) to (1A-296).
- “Me” is a methyl group
- “iPr” is an isopropyl group
- “tBu” is a t-butyl group
- “SiMe 3 ” is a trimethylsilyl group
- CN is a cyano group.
- the polycyclic aromatic amino compound represented by the general formula (1B) or the general formula (1B ′) of the present invention is a phenyloxy group, carbazolyl group or diphenylamino in the para position with respect to B (boron) in the a ring.
- a group an improvement in T1 energy (an improvement of about 0.01 to 0.1 eV) can be expected.
- HOMO on the benzene ring, which is a ring is more localized at the meta position relative to boron, and LUMO is localized at the ortho and para positions relative to boron. Therefore, the T1 energy can be particularly improved.
- the polycyclic aromatic amino compound represented by the general formula (1A) or (1B) is basically composed of two naphthalene compounds in the general formula (1A).
- an intermediate is produced by bonding one naphthalene compound and a ring with a bonding group (a group containing X 1 or X 2 ) (first reaction), and then
- a bonding group a group containing X 1 or X 2
- first reaction two naphthalene compounds are bonded to each other
- one naphthalene compound and the a ring are bonded by a bonding group (B: a group containing a boron atom).
- B a group containing a boron atom
- a general reaction such as a nucleophilic substitution reaction and an Ullmann reaction can be used for an etherification reaction, and a general reaction such as a Buchwald-Hartwig reaction can be used for an amination reaction.
- a tandem hetero Friedel-Crafts reaction continuous aromatic electrophilic substitution reaction, the same applies hereinafter
- the definitions of Ar, R 1 to R 4 , X 1 , X 2 , m, n, p, and q are the same as those of formula (1A) or formula (1B).
- the second reaction is a reaction for introducing B (boron atom) for bonding two naphthalene compounds or one naphthalene compound and a ring
- B boron atom
- X 1 and X 2 are oxygen atoms
- a hydrogen atom and n- butyllithium between X 1 and X 2 ortho-metalated with sec- butyllithium or t- butyl lithium, and the like.
- Bronsted base such as N, N-diisopropylethylamine is added to cause tandem Bora Friedel-Crafts reaction. You can get things.
- a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.
- lithium is introduced into a desired position by orthometalation.
- a bromine atom or the like is introduced at a position where lithium is to be introduced, and halogen-metal exchange is also performed.
- Lithium can be introduced at the desired location.
- This method is useful because the target product can be synthesized even in the case where ortho-metalation is not possible due to the influence of substituents.
- a polycyclic aromatic amino compound having a substituent at a desired position and X 1 and X 2 being oxygen atoms can be synthesized. it can.
- X 1 and X 2 are nitrogen atoms
- the hydrogen atom between X 1 and X 2 is first ortho-metalated with n-butyllithium or the like.
- boron tribromide and the like are added, and after lithium-boron metal exchange is performed, Brensted base such as N, N-diisopropylethylamine is added to cause tandem Bora Friedel-Crafts reaction to obtain the target product.
- a Lewis acid such as aluminum trichloride may be added to promote the reaction.
- solvent used in the above reaction are toluene, t-butylbenzene, xylene and the like.
- R 4 is plural in formula (1B) and the general formula (1B '), may form an aryl or heteroaryl ring with a ring by bonding adjacent R 4 together. Therefore, the polycyclic aromatic amino compounds represented by the general formula (1B) and the general formula (1B ′) are represented by the general formulas of the following schemes (7) and (8) depending on the mutual bonding form of the substituents in the a ring. As shown in (1B-a ′) and general formula (1B′-a ′), the ring structure constituting the compound changes. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (6) to the intermediates shown in the following schemes (7) and (8).
- the a ′ ring in the general formula (1B-a ′) and the general formula (1B′-a ′) represents an aryl ring or a heteroaryl ring formed by bonding adjacent R 4 together with the a ring.
- the orthometalation reagents used in the above schemes (1) to (10) include alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, t-butyllithium, lithium diisopropylamide, lithium tetramethyl, etc.
- alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, t-butyllithium, lithium diisopropylamide, lithium tetramethyl, etc.
- Examples include organic alkali compounds such as piperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.
- the metal-B (boron) metal exchange reagent used in the above schemes (1) to (10) includes B halides such as B trifluoride, trichloride, tribromide, and triiodide, Examples thereof include an aminated halide of B such as CIPN (NEt 2 ) 2 , an alkoxylated product of B, and an aryloxylated product of B.
- B halides such as B trifluoride, trichloride, tribromide, and triiodide
- B halides such as B trifluoride, trichloride, tribromide, and triiodide
- Examples thereof include an aminated halide of B such as CIPN (NEt 2 ) 2 , an alkoxylated product of B, and an aryloxylated product of B.
- the Bronsted base used in the above schemes (1) to (10) includes N, N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6. -Pentamethylpiperidine, N, N-dimethylaniline, N, N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar 4 BNa, Ar 4 BK, Ar 3 B, Ar 4 Si (where Ar is an aryl such as phenyl) and the like.
- a Bronsted base or a Lewis acid may be used to promote the tandem heterofriedel crafts reaction.
- B halides such as B trifluoride, trichloride, tribromide, triiodide
- hydrogen fluoride, hydrogen chloride, hydrogen bromide with the progress of the aromatic electrophilic substitution reaction
- an acid such as hydrogen iodide is generated, it is effective to use a Bronsted base that captures the acid.
- an aminated halide of B or an alkoxylated product of B is used, an amine or alcohol is produced with the progress of the aromatic electrophilic substitution reaction.
- the use of a Lewis acid that promotes the elimination is effective.
- the polycyclic aromatic amino compound of the present invention includes those in which at least a part of hydrogen atoms are substituted with deuterium and those substituted with halogen such as fluorine or chlorine.
- a compound or the like can be synthesized in the same manner as described above by using a raw material in which a desired portion is deuterated, fluorinated or chlorinated.
- the polycyclic aromatic amino compound according to the present invention can be used as a material for organic devices.
- an organic device an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, etc. are mention
- FIG. 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.
- An organic electroluminescent device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103.
- the cathode 108 provided on the electron injection layer 107.
- the organic electroluminescent element 100 is manufactured in the reverse order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer.
- a structure including the hole injection layer 103 provided above and the anode 102 provided on the hole injection layer 103 may be employed.
- each said layer may consist of a single layer, respectively, and may consist of multiple layers.
- the substrate 101 serves as a support for the organic electroluminescent device 100, and usually quartz, glass, metal, plastic, or the like is used.
- the substrate 101 is formed into a plate shape, a film shape, or a sheet shape according to the purpose.
- a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used.
- glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, polysulfone and the like are preferable.
- soda lime glass, non-alkali glass, or the like is used, and the thickness only needs to be sufficient to maintain the mechanical strength.
- the upper limit value of the thickness is, for example, 2 mm or less, preferably 1 mm or less.
- the glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass.
- soda lime glass with a barrier coat such as SiO 2 is also commercially available, so it can be used. it can.
- the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one surface in order to improve the gas barrier property, and a synthetic resin plate, film or sheet having a low gas barrier property is used as the substrate 101. When used, it is preferable to provide a gas barrier film.
- the anode 102 serves to inject holes into the light emitting layer 105.
- the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. .
- Examples of the material for forming the anode 102 include inorganic compounds and organic compounds.
- Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide) Products (IZO), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, and the like.
- Examples of the organic compound include polythiophene such as poly (3-methylthiophene), conductive polymer such as polypyrrole and polyaniline, and the like. In addition, it can select suitably from the substances currently used as an anode of an organic electroluminescent element, and can use it.
- the resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but is preferably low resistance from the viewpoint of power consumption of the light emitting element.
- an ITO substrate of 300 ⁇ / ⁇ or less functions as an element electrode, but at present, since it is possible to supply a substrate of about 10 ⁇ / ⁇ , for example, 100 to 5 ⁇ / ⁇ , preferably 50 to 5 ⁇ . It is particularly desirable to use a low resistance product of / ⁇ .
- the thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 50 to 300 nm.
- the hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104.
- the hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105.
- the hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one kind or two or more kinds of hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder. Is done.
- an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.
- a hole injection / transport material As a hole injection / transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied. The hole injection efficiency is high, and the injected holes are transported efficiently. It is desirable to do. For this purpose, it is preferable to use a substance that has a low ionization potential, a high hole mobility, excellent stability, and is less likely to generate trapping impurities during production and use.
- a polycyclic aromatic amino compound represented by the general formula (1A) or the general formula (1B) can be used as a material for forming the hole injection layer 103 and the hole transport layer 104.
- a polycyclic aromatic amino compound represented by the general formula (1A) or the general formula (1B) can be used as a material for forming the hole injection layer 103 and the hole transport layer 104.
- photoconductive materials compounds conventionally used as hole charge transport materials, p-type semiconductors, and known materials used in hole injection layers and hole transport layers of organic electroluminescence devices Any one can be selected and used.
- carbazole derivatives N-phenylcarbazole, polyvinylcarbazole, etc.
- biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole)
- triarylamine derivatives aromatic tertiary class
- polycarbonates, styrene derivatives, polyvinylcarbazole, polysilanes, etc. having the aforementioned monomers in the side chain are preferred, but light emitting devices There is no particular limitation as long as it is a compound capable of forming a thin film necessary for the fabrication of the material, injecting holes from the anode, and further transporting holes.
- organic semiconductors are strongly influenced by the doping.
- Such an organic semiconductor matrix material is composed of a compound having a good electron donating property or a compound having a good electron accepting property.
- Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping of electron donor materials.
- TCNQ tetracyanoquinone dimethane
- F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane
- the light emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied.
- the material for forming the light-emitting layer 105 may be a compound that emits light by being excited by recombination of holes and electrons (a light-emitting compound), can form a stable thin film shape, and is in a solid state It is preferable that the compound exhibits a strong light emission (fluorescence) efficiency.
- the polycyclic aromatic amino compound represented by the general formula (1A) or the general formula (1B) can be used as the material for the light emitting layer.
- the light emitting layer may be either a single layer or a plurality of layers, each formed of a light emitting layer material (host material, dopant material).
- a light emitting layer material host material, dopant material
- Each of the host material and the dopant material may be one kind or a plurality of combinations.
- the dopant material may be included in the host material as a whole, or may be included partially.
- As a doping method it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited.
- the amount of host material used depends on the type of host material and can be determined according to the characteristics of the host material.
- the standard of the amount of the host material used is preferably 50 to 99.999% by weight of the entire light emitting layer material, more preferably 80 to 99.95% by weight, and still more preferably 90 to 99.9% by weight. It is.
- the polycyclic aromatic amino compound represented by the general formula (1A) or the general formula (1B) can also be used as a host material.
- the amount of dopant material used depends on the type of dopant material, and can be determined according to the characteristics of the dopant material.
- the standard of the amount of dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and further preferably 0.1 to 10% by weight of the entire material for the light emitting layer. is there. The above range is preferable in that, for example, the concentration quenching phenomenon can be prevented.
- the polycyclic aromatic amino compound represented by the general formula (1A) or the general formula (1B) can also be used as a dopant material.
- a condensed ring derivative such as anthracene or pyrene that has been known as a light emitter for some time.
- Bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, and the like.
- dopant material which can be used together with the polycyclic aromatic amino compound represented by the said General formula (1A) or General formula (1B), It is using a known compound. It can be selected from various materials depending on the desired emission color.
- condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazoles Derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, distyrylbenzene derivatives, etc.
- condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pent
- blue to blue-green dopant materials include naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, chrysene and other aromatic hydrocarbon compounds and derivatives thereof, furan, pyrrole, thiophene, Aromatic complex such as silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene Ring compounds and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazo
- green to yellow dopant material examples include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene.
- a compound in which a substituent capable of increasing the wavelength such as aryl, heteroaryl, arylvinyl, amino, cyano is introduced into the compound exemplified as a blue-green dopant material is also a suitable example.
- orange to red dopant materials include naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone and phenanthroline as ligands, 4 -(Dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone Derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazo Derivatives, thi
- the dopant can be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13, and references cited therein.
- amines having a stilbene structure perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives or pyrene derivatives are particularly preferable.
- the amine having a stilbene structure is represented by the following formula, for example.
- Ar 1 is an m-valent group derived from aryl having 6 to 30 carbon atoms
- Ar 2 and Ar 3 are each independently aryl having 6 to 30 carbon atoms
- Ar 1 to Ar At least one of 3 has a stilbene structure
- Ar 1 to Ar 3 may be substituted with aryl, heteroaryl, alkyl, trisubstituted silyl (silyl substituted with aryl and / or alkyl) or cyano.
- m is an integer from 1 to 4.
- the amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula.
- Ar 2 and Ar 3 are each independently aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 are aryl, heteroaryl, alkyl, tri-substituted silyl (aryl and / or alkyl trivalent). Optionally substituted with silyl) or cyano.
- aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrycenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenylyl , Distyrylfluorenyl and the like.
- amines having a stilbene structure include N, N, N ′, N′-tetra (4-biphenylyl) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (1-naphthyl) ) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (2-naphthyl) -4,4′-diaminostilbene, N, N′-di (2-naphthyl) -N, N '-Diphenyl-4,4'-diaminostilbene, N, N'-di (9-phenanthryl) -N, N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis [4 "-bis (Diphenylamino) styryl] -biphenyl, 1,4-bis [4′-bis (diphenylamino)
- perylene derivatives examples include 3,10-bis (2,6-dimethylphenyl) perylene, 3,10-bis (2,4,6-trimethylphenyl) perylene, 3,10-diphenylperylene, 3,4- Diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3- (1'-pyrenyl) -8,11-di (t-butyl) perylene 3- (9′-anthryl) -8,11-di (t-butyl) perylene, 3,3′-bis (8,11-di (t-butyl) perylenyl), and the like.
- JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, Perylene derivatives described in JP-A No. 2000-34234, JP-A No. 2001-267075, JP-A No. 2001-217077 and the like may be used.
- borane derivatives examples include 1,8-diphenyl-10- (dimesitylboryl) anthracene, 9-phenyl-10- (dimesitylboryl) anthracene, 4- (9′-anthryl) dimesitylborylnaphthalene, 4- (10 ′ -Phenyl-9'-anthryl) dimesitylborylnaphthalene, 9- (dimesitylboryl) anthracene, 9- (4'-biphenylyl) -10- (dimesitylboryl) anthracene, 9- (4 '-(N-carbazolyl) phenyl) And -10- (dimesitylboryl) anthracene.
- the aromatic amine derivative is represented by the following formula, for example.
- Ar 4 is an n-valent group derived from aryl having 6 to 30 carbon atoms
- Ar 5 and Ar 6 are each independently aryl having 6 to 30 carbon atoms
- Ar 4 to Ar 6 are , Aryl, heteroaryl, alkyl, trisubstituted silyl (silyl substituted with aryl and / or alkyl) or cyano
- n is an integer from 1 to 4.
- Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene or pyrene
- Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms
- Ar 4 to Ar 6 Is more preferably an aromatic amine derivative, optionally substituted with aryl, heteroaryl, alkyl, trisubstituted silyl (silyl substituted with aryl and / or alkyl) or cyano
- n is 2.
- aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, pentacenyl and the like.
- the chrysene type includes, for example, N, N, N ′, N′-tetraphenylchrysene-6,12-diamine, N, N, N ′, N′-tetra (p-tolyl) Chrysene-6,12-diamine, N, N, N ′, N′-tetra (m-tolyl) chrysene-6,12-diamine, N, N, N ′, N′-tetrakis (4-isopropylphenyl) chrysene -6,12-diamine, N, N, N ', N'-tetra (naphthalen-2-yl) chrysene-6,12-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) ) Chrysene-6,12-diamine, N, N′-diphenyl-N, N′-bis (4
- Examples of the pyrene series include N, N, N ′, N′-tetraphenylpyrene-1,6-diamine, N, N, N ′, N′-tetra (p-tolyl) pyrene-1,6.
- anthracene system examples include N, N, N, N-tetraphenylanthracene-9,10-diamine, N, N, N ′, N′-tetra (p-tolyl) anthracene-9,10-diamine.
- Examples of coumarin derivatives include coumarin-6 and coumarin-334. Moreover, you may use the coumarin derivative described in Unexamined-Japanese-Patent No. 2004-43646, Unexamined-Japanese-Patent No. 2001-76876, and Unexamined-Japanese-Patent No. 6-298758.
- Examples of the pyran derivative include the following DCM and DCJTB. Also, JP 2005-126399, JP 2005-097283, JP 2002-234892, JP 2001-220577, JP 2001-081090, and JP 2001-052869. Alternatively, pyran derivatives described in the above may be used.
- the electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106.
- the electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105.
- the electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more electron transport / injection materials or a mixture of the electron transport / injection material and the polymer binder.
- the electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and further transporting the electrons. It is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is preferable to use a substance that has a high electron affinity, a high electron mobility, excellent stability, and is unlikely to generate trapping impurities during production and use. However, considering the transport balance between holes and electrons, if the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination is mainly played, the electron transport capability is much higher. Even if it is not high, the effect of improving the luminous efficiency is equivalent to that of a material having a high electron transport capability. Therefore, the electron injection / transport layer in this embodiment may include a function of a layer that can efficiently block the movement of holes.
- a material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 a polycyclic aromatic amino compound represented by the above general formula (1A) or general formula (1B) can be used.
- it can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in electron injection layers and electron transport layers of organic electroluminescent devices. .
- a compound composed of an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus It is preferable to contain at least one selected from pyrrole derivatives, condensed ring derivatives thereof, and metal complexes having electron-accepting nitrogen.
- condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives Quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives.
- metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.
- electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazoles.
- metal complexes having electron-accepting nitrogen can also be used, such as hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. can give.
- the above-mentioned materials can be used alone, but they may be mixed with different materials.
- quinolinol metal complexes Among the materials described above, quinolinol metal complexes, bipyridine derivatives, phenanthroline derivatives or borane derivatives are preferred.
- the quinolinol-based metal complex is a compound represented by the following general formula (E-1).
- R 1 to R 6 are each independently hydrogen, fluorine, alkyl, aralkyl, alkenyl, cyano, alkoxy or aryl
- M is Li, Al, Ga, Be or Zn
- n is 1 It is an integer of ⁇ 3.
- quinolinol metal complexes include 8-quinolinol lithium, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8-quinolinolato) aluminum, tris (3 , 4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) ( Phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolato) aluminum, bis (2-methyl-8- Quinolinolato) (4- Tylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolate)
- the bipyridine derivative is a compound represented by the following general formula (E-2).
- G represents a simple bond or an n-valent linking group, and n is an integer of 2 to 8.
- Carbons not used for the pyridine-pyridine or pyridine-G bond may be substituted with aryl, heteroaryl, alkyl or cyano.
- G in the general formula (E-2) examples include the following structural formulas.
- each R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl.
- pyridine derivative examples include 2,5-bis (2,2′-pyridin-6-yl) -1,1-dimethyl-3,4-diphenylsilole, 2,5-bis (2,2′- Pyridin-6-yl) -1,1-dimethyl-3,4-dimesitylsilole, 2,5-bis (2,2′-pyridin-5-yl) -1,1-dimethyl-3,4 Diphenylsilole, 2,5-bis (2,2′-pyridin-5-yl) -1,1-dimethyl-3,4-dimesitylsilole, 9,10-di (2,2′-pyridine-6) -Yl) anthracene, 9,10-di (2,2′-pyridin-5-yl) anthracene, 9,10-di (2,3′-pyridin-6-yl) anthracene, 9,10-di (2 , 3′-Pyridin-5-yl)
- the phenanthroline derivative is a compound represented by the following general formula (E-3-1) or (E-3-2).
- R 1 to R 8 are each independently hydrogen, alkyl (methyl, ethyl, isopropyl, hydroxyethyl, methoxymethyl, trifluoromethyl, t-butyl, cyclopentyl, cyclohexyl, benzyl, etc.), alkyloxy ( Methoxy, ethoxy, isopropoxy, butoxy, etc.), aryloxy (phenoxy, 1-naphthyloxy, 4-tolyloxy, etc.), halogen (fluorine, chlorine, bromine, iodine, etc.), aryl (phenyl, naphthyl, p-tolyl, p) -Chlorophenyl, etc.), alkylthio (methylthio, ethylthio, isopropylthio, etc.), arylthio (phenyl
- phenanthroline derivatives include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10-phenanthroline- 2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1,10-phenanthroline-5-yl) benzene, 9,9′-difluoro -Bi (1,10-phenanthroline-5-yl), bathocuproin, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene and the like.
- a phenanthroline derivative is used for the electron transport layer and the electron injection layer.
- the substituent itself has a three-dimensional structure, or a phenanthroline skeleton or Those having a three-dimensional structure by steric repulsion with adjacent substituents, or those obtained by linking a plurality of phenanthroline skeletons are preferred.
- a compound containing a conjugated bond, a substituted or unsubstituted aromatic hydrocarbon, or a substituted or unsubstituted aromatic heterocycle in the linking unit is more preferable.
- the borane derivative is a compound represented by the following general formula (E-4), and is disclosed in detail in JP-A-2007-27587.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- R 13 to R 16 are each independently an optionally substituted alkyl or an optionally substituted aryl
- X is an optionally substituted arylene
- Y is Optionally substituted aryl having 16 or less carbon atoms, substituted boryl, or optionally substituted carbazolyl
- n is each independently an integer of 0 to 3.
- substituent in the case of “which may be substituted” or “substituted” include aryl, heteroaryl and alkyl.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- R 13 to R 16 are each independently an optionally substituted alkyl or an optionally substituted aryl
- R 21 and R 22 are each independently hydrogen, alkyl, At least one of optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocyclic ring, or cyano
- X 1 is optionally substituted arylene having 20 or less carbon atoms.
- N is each independently an integer from 0 to 3
- m is each independently an integer from 0 to 4.
- substituent in the case of “which may be substituted” or “substituted” include aryl, heteroaryl and alkyl.
- R 31 to R 34 are each independently methyl, isopropyl or phenyl
- R 35 and R 36 are each independently hydrogen, methyl, isopropyl or phenyl. It is.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- Each of R 13 to R 16 independently represents an optionally substituted alkyl or an optionally substituted aryl, and X 1 represents an optionally substituted arylene having 20 or less carbon atoms.
- n is each independently an integer of 0 to 3.
- substituent in the case of “which may be substituted” or “substituted” include aryl, heteroaryl and alkyl.
- R 31 to R 34 are each independently any of methyl, isopropyl or phenyl
- R 35 and R 36 are each independently any of hydrogen, methyl, isopropyl or phenyl It is.
- each of R 11 and R 12 independently represents at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
- Each of R 13 to R 16 independently represents an optionally substituted alkyl or an optionally substituted aryl, and X 1 represents an optionally substituted arylene having 10 or less carbon atoms.
- Y 1 is optionally substituted aryl having 14 or less carbon atoms, and n is each independently an integer of 0 to 3.
- substituent in the case of “which may be substituted” or “substituted” include aryl, heteroaryl and alkyl.
- R 31 to R 34 are each independently methyl, isopropyl or phenyl
- R 35 and R 36 are each independently hydrogen, methyl, isopropyl or phenyl. It is.
- the benzimidazole derivative is a compound represented by the following general formula (E-5).
- Ar 1 to Ar 3 are each independently hydrogen or aryl having 6 to 30 carbon atoms which may be substituted. Examples of the substituent in the case of “optionally substituted” include aryl, heteroaryl, alkyl, cyano and the like. Particularly preferred is a benzimidazole derivative wherein Ar 1 is anthryl optionally substituted with aryl, heteroaryl, alkyl or cyano.
- aryl having 6 to 30 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, acenaphthylene-1-yl, acenaphthylene-3-yl, acenaphthylene-4-yl, acenaphthylene-5-yl, and fluorene-1- Yl, fluoren-2-yl, fluoren-3-yl, fluoren-4-yl, fluoren-9-yl, phenalen-1-yl, phenalen-2-yl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-anthryl, 2-anthryl, 9-anthryl, fluoranthen-1-yl, fluoranthen-2-yl, fluoranthen-3-yl, fluoranthen-7-yl, fluoranthen-8-yl, Triphenylene-1-yl, 2-
- benzimidazole derivative examples include 1-phenyl-2- (4- (10-phenylanthracen-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- (naphthalene-2) -Yl) anthracen-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -1- Phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalen-2-yl) anthracen-9-yl) -1,2-diphenyl-1H-benzo [d] imidazole, 1- (4- (10 -(Naphthalen-2-yl) anthracen-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (n)-
- the electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer.
- a substance capable of reducing the material forming the electron transport layer or the electron injection layer various substances can be used as long as they have a certain reducing ability.
- Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2. 9eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and alkaline earth metals such as those having a work function of 2.9 eV or less are particularly preferable.
- a more preferable reducing substance is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs.
- alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL element can be improved and the lifetime can be extended.
- a reducing substance having a work function of 2.9 eV or less a combination of these two or more alkali metals is also preferable.
- a combination containing Cs for example, Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
- the cathode 108 serves to inject electrons into the light emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.
- the material for forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, but the same material as that for forming the anode 102 can be used.
- metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or alloys thereof (magnesium-silver alloy, magnesium -Indium alloys, aluminum-lithium alloys such as lithium fluoride / aluminum, etc.) are preferred.
- Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics.
- metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example.
- the method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.
- the materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but as a polymer binder, polyvinyl chloride, polycarbonate, Polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin It can also be used by dispersing it in solvent-soluble resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, etc. is there.
- solvent-soluble resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins,
- Each layer constituting the organic electroluminescent element is formed by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method or cast method, coating method, etc. It can be formed by using a thin film.
- the film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like.
- the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, and the like.
- the deposition conditions are generally as follows: heating temperature of the deposition crucible +50 to + 400 ° C., vacuum 10 ⁇ 6 to 10 ⁇ 3 Pa, deposition rate 0.01 to 50 nm / second, substrate temperature ⁇ 150 to + 300 ° C., film thickness 2 nm It is preferable to set appropriately in the range of ⁇ 5 ⁇ m.
- an organic electric field composed of an anode / hole injection layer / hole transport layer / a light emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode.
- a method for manufacturing a light-emitting element will be described.
- a thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode.
- a host material and a dopant material are co-evaporated to form a thin film to form a light emitting layer.
- An electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by vapor deposition. By forming it as a cathode, a desired organic electroluminescent element can be obtained.
- the order of preparation may be reversed, and the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode may be fabricated in this order. Is possible.
- the anode When a DC voltage is applied to the organic electroluminescent device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, the organic electroluminescent device is transparent or translucent. Luminescence can be observed from the electrode side (anode or cathode, and both). The organic electroluminescence device emits light when a pulse current or an alternating current is applied. The alternating current waveform to be applied may be arbitrary.
- the present invention can also be applied to a display device provided with an organic electroluminescent element or a lighting device provided with an organic electroluminescent element.
- a display device or an illuminating device including an organic electroluminescent element can be manufactured by a known method such as connecting the organic electroluminescent element according to the present embodiment and a known driving device, such as direct current driving, pulse driving, or alternating current. It can be driven by appropriately using a known driving method such as driving.
- Examples of the display device include a panel display such as a color flat panel display, and a flexible display such as a flexible color organic electroluminescence (EL) display (for example, JP-A-10-335066 and JP-A-2003-321546). Gazette, JP-A-2004-281086, etc.).
- Examples of the display method of the display include a matrix and / or segment method. Note that the matrix display and the segment display may coexist in the same panel.
- a matrix is a pixel in which pixels for display are arranged two-dimensionally, such as a grid or mosaic, and displays characters and images as a set of pixels.
- the shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 ⁇ m or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become.
- monochrome display pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type.
- the matrix driving method may be either a line sequential driving method or an active matrix.
- the line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.
- a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light.
- a predetermined region is caused to emit light.
- the time and temperature display in a digital clock or a thermometer the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned.
- the illuminating device examples include an illuminating device such as indoor lighting, a backlight of a liquid crystal display device, and the like (for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A).
- the backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like.
- a backlight for liquid crystal display devices especially personal computers for which thinning is an issue, considering that conventional methods are made of fluorescent lamps and light guide plates, it is difficult to reduce the thickness.
- the backlight using the light emitting element according to the embodiment is thin and lightweight.
- polycyclic aromatic amino compound according to the present invention can be used for production of an organic field effect transistor or an organic thin film solar cell in addition to the organic electroluminescent element described above.
- An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and includes a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the current can be controlled by arbitrarily blocking the flow of electrons (or holes) flowing between the source electrode and the drain electrode.
- Field effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.
- the structure of the organic field effect transistor is usually provided with a source electrode and a drain electrode in contact with the organic semiconductor active layer formed using the polycyclic aromatic amino compound according to the present invention,
- the gate electrode only needs to be provided with the insulating layer (dielectric layer) in contact therewith.
- Examples of the element structure include the following structures.
- Substrate / gate electrode / insulator layer / source electrode / drain electrode / organic semiconductor active layer (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode / drain electrode (3) substrate / organic Semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode It can be applied as a pixel drive switching element of an active matrix drive type liquid crystal display or an organic electroluminescence display.
- Organic thin-film solar cells have a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass.
- the photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side.
- the polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer, depending on its physical properties.
- the polycyclic aromatic amino compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell.
- the organic thin film solar cell may appropriately include a hole block layer, an electron block layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like.
- known materials used for the organic thin film solar cell can be appropriately selected and used in combination.
- reaction solution was depressurized to distill off low-boiling components and then cooled to ⁇ 40 ° C.
- Boron bromide (4.6 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hr, cooled to 0 ° C., N-ethyldiisopropylamine (4.0 g) was added, and 5 ° C. at 125 ° C. was added.
- the reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution was added.
- reaction solution was decompressed to distill off low-boiling components, then cooled to ⁇ 30 ° C., and boron tribromide (10.0 g) was added.
- the mixture was warmed to room temperature and stirred for 0.5 hour, then cooled to 0 ° C., N-ethyldiisopropylamine (4.0 g) was added, and the mixture was stirred at room temperature for 10 minutes.
- aluminum chloride (7.1 g) was added and heated at 100 ° C. for 6 hours.
- the reaction solution was cooled to room temperature, and the reaction was stopped by adding an aqueous potassium acetate solution, and then ethyl acetate was added for liquid separation.
- silica gel short pass column eluent: toluene
- column purification was performed with NH 2 silica
- polycyclic aromatic amino compounds of the present invention can be synthesized by a method according to the synthesis example described above by appropriately changing the raw material compound.
- the measuring device used was an absolute PL quantum yield measuring device C9920-02G manufactured by Hamamatsu Photonics Co., Ltd.
- the excitation light source was a Xe lamp spectral light source 150W, and the excitation light was 320 nm monochromatic light.
- fluorescence quantum yield eta PL is given by the following equation.
- N emission is the number of photons emitted from the material
- N Absorption is the number of photons absorbed by the material
- the fluorescence quantum yield is obtained as the ratio.
- ⁇ is the correction coefficient of the measurement system
- ⁇ is the wavelength
- h is Planck's constant
- c is the speed of light
- I em ( ⁇ ) is the emission intensity of the sample
- I ex ( ⁇ ) is the intensity of the excitation light before the sample is installed
- I ′ ex ( ⁇ ) is the excitation light intensity observed when the sample is irradiated with the excitation light.
- the fluorescence quantum yield can be measured by performing two spectrum observations of I em and I ′ ex + I em .
- the same synthetic quartz substrate as the PMMA dispersion film sample was used as a blank substrate.
- the blank substrate was set in a sample holder for absolute PL quantum yield, and I ex ( ⁇ ) was measured.
- the blank substrate was removed from the sample holder, a PMMA dispersed film sample was set, and I ′ ex ( ⁇ ) + I em ( ⁇ ) was observed.
- Table 1 The measurement results of the fluorescence quantum yield are shown in Table 1.
- Table 2A and Table 2B show the results of measuring the fluorescence quantum yield of the comparative compound by the same method as the compound of the present invention, together with the compound structure and the compound number described in International Publication No. 2015/102118. It is on.
- Organic EL elements according to Examples 1 to 3 and Comparative Examples 1 to 11 were prepared, and voltage (V), EL emission wavelength (nm), and external quantum efficiency (%), which are characteristics at 1000 cd / m 2 emission, respectively. Then, the time for maintaining a luminance of 90% or more of the initial luminance when driven at a constant current at a current density of 10 mA / cm 2 was measured.
- the material composition of each layer in the produced organic EL element is shown in Table 3 below.
- the dopant materials in Comparative Examples 1 to 10 are all known compounds disclosed in International Publication No. 2015/102118.
- HI means N 4 , N 4 ′ -diphenyl-N 4 , N 4 ′ -bis (9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl] -4,4 '-Diamine
- HAT-CN is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile
- HT is N-([1,1′-biphenyl] -4-yl)- N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl)-[1,1′-biphenyl] -4-amine
- BH1 is 9-phenyl-10- (4-phenylnaphthalene- 1-yl) anthracene
- ET5 is 9- (7- (dimesitylboryl) -9,9-dimethyl-9H-fluoren-2-yl) -3,6-dimethyl-9H-carbazole
- Example 1 ⁇ Device using compound (1A-173) as dopant in light-emitting layer>
- This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (Changzhou Industrial Co., Ltd.), and each of HI, HAT-CN, HT, BH1, the compound of the present invention (1A-173), ET5 and ET6 A tantalum vapor deposition crucible containing this, and an aluminum nitride vapor deposition crucible containing each of Liq, magnesium and silver were attached.
- the following layers were sequentially formed on the ITO film of the transparent support substrate.
- the vacuum chamber was depressurized to 2.0 ⁇ 10 ⁇ 4 Pa, and first, HI was heated and evaporated to a film thickness of 40 nm, and then HAT-CN was heated and evaporated to a film thickness of 5 nm. Further, HT was heated and evaporated to a film thickness of 25 nm to form a three-layered hole injection layer and a hole transport layer.
- BH1 and the compound of the present invention (1A-173) were heated at the same time and evaporated to a thickness of 25 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of BH1 to the compound of the present invention (1A-173) was approximately 98 to 2.
- ET5 was heated and evaporated to a thickness of 5 nm to form a first electron transport layer.
- ET6 and Liq were heated at the same time and evaporated to a film thickness of 25 nm to form a second electron transport layer.
- the deposition rate was adjusted so that the weight ratio of ET6 to Liq was approximately 1: 1.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- Liq was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
- magnesium and silver were heated at the same time and evaporated to a thickness of 100 nm to form a cathode to obtain an organic electroluminescent device.
- the deposition rate was adjusted between 0.1 nm and 10 nm / second so that the atomic ratio of magnesium and silver was 10: 1.
- the characteristics at 1000 cd / m 2 emission were measured.
- the drive voltage was 4.25 V and the external quantum efficiency was 6.1% (blue emission with a wavelength of about 468 nm).
- the time for maintaining a luminance of 90% or more of the initial luminance was 223 hours.
- Example 2 ⁇ Device using compound (1A-173) as dopant in light-emitting layer>
- An organic EL device was obtained by the same method as in Example 1 except that the evaporation rate was adjusted so that the weight ratio of BH1 to the compound of the present invention (1A-173) was about 95: 5 in the light emitting layer.
- the driving voltage is 3.95 V
- the external quantum efficiency is 6.7% (blue emission with a wavelength of about 470 nm)
- the time for maintaining the luminance of 90% or more of the initial luminance was 270 hours.
- Example 3> ⁇ Device using Compound (1A-1) as a dopant in the light emitting layer>
- An organic EL device was obtained in the same manner as in Example 1 except that the compound (1A-173), which was the dopant for the light emitting layer, was changed to the compound (1A-1).
- the driving voltage is 4.25 V
- the external quantum efficiency is 6.0% (blue emission with a wavelength of about 465 nm)
- the time for maintaining 90% or more of the initial luminance was 180 hours.
- ⁇ Comparative example 2> ⁇ Device using known compound (1-100) as dopant in light-emitting layer>
- An organic EL device was obtained in the same manner as in Example 1 except that the compound (1A-173) as the dopant for the light emitting layer was replaced with the known compound (1-100).
- the driving voltage is 4.72 V
- the external quantum efficiency is 2.8% (blue emission with a wavelength of about 456 nm)
- the time for maintaining the luminance of 90% or more of the initial luminance was 57 hours.
- each layer in the produced organic EL element is shown in Table 5 below.
- the dopant material in the comparative example 12 is a well-known compound disclosed by the international publication 2015/102118.
- Example 4 ⁇ Device using Compound (1A-153) as a dopant in the light emitting layer>
- This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (Changzhou Industrial Co., Ltd.), and each of HI, HAT-CN, HT, BH1, the compound of the present invention (1A-153), ET5 and ET6 A tantalum vapor deposition crucible containing this, and an aluminum nitride vapor deposition crucible containing each of Liq, magnesium and silver were attached.
- the following layers were sequentially formed on the ITO film of the transparent support substrate.
- the vacuum chamber was depressurized to 2.0 ⁇ 10 ⁇ 4 Pa, and first, HI was heated and evaporated to a film thickness of 40 nm, and then HAT-CN was heated and evaporated to a film thickness of 5 nm. Further, HT was heated and evaporated to a film thickness of 25 nm to form a three-layered hole injection layer and a hole transport layer.
- BH1 and the compound of the present invention (1A-153) were heated at the same time and evaporated to a thickness of 25 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of BH1 to the compound of the present invention (1A-153) was approximately 98 to 2.
- ET5 was heated and evaporated to a thickness of 5 nm to form a first electron transport layer.
- ET6 and Liq were heated at the same time and evaporated to a film thickness of 25 nm to form a second electron transport layer.
- the deposition rate was adjusted so that the weight ratio of ET6 to Liq was approximately 1: 1.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- Liq was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
- magnesium and silver were heated at the same time and evaporated to a thickness of 100 nm to form a cathode to obtain an organic electroluminescent device.
- the deposition rate was adjusted between 0.1 nm and 10 nm / second so that the atomic ratio of magnesium and silver was 10: 1.
- the characteristics at 1000 cd / m 2 emission were measured.
- the drive voltage was 3.94 V and the external quantum efficiency was 6.8% (blue emission with a wavelength of about 460 nm).
- the time for maintaining a luminance of 90% or more of the initial luminance was 161 hours.
- Table 7 shows the material configuration of each layer in the produced organic EL element.
- the dopant material in the comparative example 13 is a well-known compound disclosed by the international publication 2015/102118.
- HT2 is N, N-bis (4-dibenzo [b, d] furan-4-yl) phenyl)-[1,1 ′: 4 ′, 1 ′′ -terphenyl] -4-amine
- BH2 is 2- (10-phenylanthracen-9-yl) naphtho [2,3-b] benzofuran
- ET7 is 4,6,8,10-tetraphenyl-5,9-dioxa-13b-boranenaphtho [3,2,1-de] anthracene
- ET8 is 3,3 ′-((2-phenylanthracene-9,10-diyl) bis (4,1-phenylene)) bis (4-methylpyridine) is there.
- the chemical structure is shown below.
- Example 5 ⁇ Device using Compound (1A-1) as a dopant in the light emitting layer>
- This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (Changzhou Industrial Co., Ltd.), and each of HI, HAT-CN, HT, HT2, BH2, compound (1A-1) of the present invention, ET7 and ET8 A tantalum vapor deposition crucible containing Li, and an aluminum nitride vapor deposition crucible containing Liq, magnesium and silver were mounted.
- the following layers were sequentially formed on the ITO film of the transparent support substrate.
- the vacuum chamber is depressurized to 2.0 ⁇ 10 ⁇ 4 Pa, first, HI is heated and evaporated to a film thickness of 40 nm, and then HAT-CN is heated and evaporated to a film thickness of 5 nm. Thus, a hole injection layer composed of two layers was formed.
- HT was heated and vapor-deposited to a film thickness of 15 nm, and then HT2 was heated and vapor-deposited to a film thickness of 10 nm to form a two-hole hole transport layer.
- BH2 and the compound (1A-1) of the present invention were simultaneously heated and evaporated to a thickness of 25 nm to form a light emitting layer.
- the deposition rate was adjusted so that the weight ratio of BH2 to the compound (1A-1) of the present invention was approximately 98 to 2.
- ET7 was heated and evaporated to a thickness of 5 nm to form a first electron transport layer.
- ET8 and Liq were heated at the same time and evaporated to a film thickness of 25 nm to form a second electron transport layer.
- the deposition rate was adjusted so that the weight ratio of ET8 to Liq was approximately 1: 1.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- Liq was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
- magnesium and silver were heated at the same time and evaporated to a thickness of 100 nm to form a cathode to obtain an organic electroluminescent device.
- the deposition rate was adjusted between 0.1 nm and 10 nm / second so that the atomic ratio of magnesium and silver was 10: 1.
- the characteristics at 1000 cd / m 2 emission were measured.
- the drive voltage was 3.33 V and the external quantum efficiency was 6.4% (blue emission with a wavelength of about 463 nm).
- the time for maintaining a luminance of 90% or more of the initial luminance was 655 hours.
- a part of the polycyclic aromatic amino compound represented by the general formula (1A) or the general formula (1B) according to the present invention is evaluated as an organic EL element material, and is an excellent organic device material.
- Other compounds that have not been evaluated are compounds having the same basic skeleton and having a similar structure as a whole, and those skilled in the art will similarly recognize that they are excellent organic device materials. Understandable.
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Abstract
Description
Arは、それぞれ独立して、アリールまたはヘテロアリールであり、
R1~R4は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシ、トリアルキルシリル、アリールオキシまたはシアノであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノまたはアルキルで置換されていてもよく、
R4が複数の場合、隣接するR4同士は結合してa環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシ、トリアルキルシリル、アリールオキシまたはシアノで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノまたはアルキルで置換されていてもよく、
R1とR3が隣接する場合には、これらは-O-、-S-、-C(-R)2-または単結合により結合していてもよく、前記-C(-R)2-のRは水素または炭素数1~6のアルキルであり、
mは0~3の整数であり、nはそれぞれ独立して0からArに最大置換可能な数までの整数であり、pは0~4の整数であり、qはそれぞれ独立して0~5の整数であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルであり、また、X2が前記N-Rである場合のRは-O-、-S-、-C(-R)2-または単結合により前記a環と結合していてもよく、前記-C(-R)2-のRは水素または炭素数1~6のアルキルであり、そして、
式(1A)または式(1B)で表される化合物における少なくとも1つの水素はハロゲンまたは重水素で置換されていてもよい。)
R2~R4は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
R4が複数の場合、隣接するR4同士は結合してa環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
mは0~3の整数であり、nはそれぞれ独立して0からArに最大置換可能な数までの整数であり、pは0~4の整数であり、qは0であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルである、
項1に記載する多環芳香族アミノ化合物。
R2~R4は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
R4が複数の場合、隣接するR4同士は結合してa環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
mは0~3の整数であり、nはそれぞれ独立して0~5の整数であり、pは0~4の整数であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルである。)
R2およびR3は、それぞれ独立して、水素、炭素数6~30のアリール、炭素数2~30のヘテロアリール、炭素数6~30のジアリールアミノ、炭素数1~24のアルキル、炭素数1~24のアルコキシ、炭素数1~4のアルキルを有するトリアルキルシリルまたは炭素数6~30のアリールオキシであり、これらにおける少なくとも1つの水素は炭素数6~16のアリール、炭素数2~25のヘテロアリールまたは炭素数1~18のアルキルで置換されていてもよく、
mは0~3の整数であり、nはそれぞれ独立して0~5の整数であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~10のアリール、炭素数2~10のヘテロアリールまたは炭素数1~4のアルキルである。)
mは0または1であり、nはそれぞれ独立して0または1であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~10のアリール、炭素数2~10のヘテロアリールまたは炭素数1~4のアルキルである、
項4に記載する多環芳香族アミノ化合物。
本願発明は、下記一般式(1A)または一般式(1B)で表される多環芳香族アミノ化合物である。また、本願発明は、好ましくは、下記一般式(1A’)または一般式(1B’)で表される多環芳香族アミノ化合物である。
一般式(1A)または一般式(1B)における、Arをフェニル基に限定し、R1~R4の置換基やその数のm、n、pおよびqを適宜限定したものが一般式(1A’)または一般式(1B’)である。
一般式(1A)や(1B)で表される多環芳香族アミノ化合物は、基本的には、まず一般式(1A)の場合は2つのナフタレン系化合物同士、一般式(1B)の場合は1つのナフタレン系化合物とa環とを結合基(X1やX2を含む基)で結合させることで中間体を製造し(第1反応)、その後に、一般式(1A)の場合は2つのナフタレン系化合物同士、一般式(1B)の場合は1つのナフタレン系化合物とa環とを結合基(B:ホウ素原子を含む基)で結合させることで最終生成物を製造することができる(第2反応)。第1反応では、例えばエーテル化反応であれば、求核置換反応、ウルマン反応といった一般的反応が利用でき、アミノ化反応で有ればブッフバルト-ハートウィッグ反応といった一般的反応が利用できる。また、第2反応では、タンデムヘテロフリーデルクラフツ反応(連続的な芳香族求電子置換反応、以下同様)が利用できる。なお、以下の各スキームにおいてAr、R1~R4、X1、X2、m、n、pおよびqの定義は式(1A)または式(1B)のそれらの定義と同一である。
本発明に係る多環芳香族アミノ化合物は、例えば、有機電界発光素子の材料として用いることができる。以下に、本実施形態に係る有機EL素子について図面に基づいて詳細に説明する。図1は、本実施形態に係る有機EL素子を示す概略断面図である。
図1に示された有機電界発光素子100は、基板101と、基板101上に設けられた陽極102と、陽極102の上に設けられた正孔注入層103と、正孔注入層103の上に設けられた正孔輸送層104と、正孔輸送層104の上に設けられた発光層105と、発光層105の上に設けられた電子輸送層106と、電子輸送層106の上に設けられた電子注入層107と、電子注入層107の上に設けられた陰極108とを有する。
基板101は、有機電界発光素子100の支持体となるものであり、通常、石英、ガラス、金属、プラスチックなどが用いられる。基板101は、目的に応じて板状、フィルム状、またはシート状に形成され、例えば、ガラス板、金属板、金属箔、プラスチックフィルム、プラスチックシートなどが用いられる。なかでも、ガラス板、および、ポリエステル、ポリメタクリレート、ポリカーボネート、ポリスルホンなどの透明な合成樹脂製の板が好ましい。ガラス基板であれば、ソーダライムガラスや無アルカリガラスなどが用いられ、また、厚みも機械的強度を保つのに十分な厚みがあればよいので、例えば、0.2mm以上あればよい。厚さの上限値としては、例えば、2mm以下、好ましくは1mm以下である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、SiO2などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することができる。また、基板101には、ガスバリア性を高めるために、少なくとも片面に緻密なシリコン酸化膜などのガスバリア膜を設けてもよく、特にガスバリア性が低い合成樹脂製の板、フィルムまたはシートを基板101として用いる場合にはガスバリア膜を設けるのが好ましい。
陽極102は、発光層105へ正孔を注入する役割を果たすものである。なお、陽極102と発光層105との間に正孔注入層103および/または正孔輸送層104が設けられている場合には、これらを介して発光層105へ正孔を注入することになる。
正孔注入層103は、陽極102から移動してくる正孔を、効率よく発光層105内または正孔輸送層104内に注入する役割を果たすものである。正孔輸送層104は、陽極102から注入された正孔または陽極102から正孔注入層103を介して注入された正孔を、効率よく発光層105に輸送する役割を果たすものである。正孔注入層103および正孔輸送層104は、それぞれ、正孔注入・輸送材料の一種または二種以上を積層、混合するか、正孔注入・輸送材料と高分子結着剤の混合物により形成される。また、正孔注入・輸送材料に塩化鉄(III)のような無機塩を添加して層を形成してもよい。
発光層105は、電界を与えられた電極間において、陽極102から注入された正孔と、陰極108から注入された電子とを再結合させることにより発光するものである。発光層105を形成する材料としては、正孔と電子との再結合によって励起されて発光する化合物(発光性化合物)であればよく、安定な薄膜形状を形成することができ、かつ、固体状態で強い発光(蛍光)効率を示す化合物であるのが好ましい。本発明では、発光層用の材料として、上記一般式(1A)または一般式(1B)で表される多環芳香族アミノ化合物を用いることができる。
また、特開2003-347056号公報、および特開2001-307884号公報などに記載されたスチルベン構造を有するアミンを用いてもよい。
また、特開平11-97178号公報、特開2000-133457号公報、特開2000-26324号公報、特開2001-267079号公報、特開2001-267078号公報、特開2001-267076号公報、特開2000-34234号公報、特開2001-267075号公報、および特開2001-217077号公報などに記載されたペリレン誘導体を用いてもよい。
また、国際公開第2000/40586号パンフレットなどに記載されたボラン誘導体を用いてもよい。
また、特開2006-156888号公報などに記載された芳香族アミン誘導体を用いてもよい。
また、特開2004-43646号公報、特開2001-76876号公報、および特開平6-298758号公報などに記載されたクマリン誘導体を用いてもよい。
電子注入層107は、陰極108から移動してくる電子を、効率よく発光層105内または電子輸送層106内に注入する役割を果たすものである。電子輸送層106は、陰極108から注入された電子または陰極108から電子注入層107を介して注入された電子を、効率よく発光層105に輸送する役割を果たすものである。電子輸送層106および電子注入層107は、それぞれ、電子輸送・注入材料の一種または二種以上を積層、混合するか、電子輸送・注入材料と高分子結着剤の混合物により形成される。
陰極108は、電子注入層107および電子輸送層106を介して、発光層105に電子を注入する役割を果たすものである。
以上の正孔注入層、正孔輸送層、発光層、電子輸送層および電子注入層に用いられる材料は単独で各層を形成することができるが、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ(N-ビニルカルバゾール)、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルホン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリアミド、エチルセルロース、酢酸ビニル樹脂、ABS樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
有機電界発光素子を構成する各層は、各層を構成すべき材料を蒸着法、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、印刷法、スピンコート法またはキャスト法、コーティング法などの方法で薄膜とすることにより、形成することができる。このようにして形成された各層の膜厚については特に限定はなく、材料の性質に応じて適宜設定することができるが、通常2nm~5000nmの範囲である。膜厚は通常、水晶発振式膜厚測定装置などで測定できる。蒸着法を用いて薄膜化する場合、その蒸着条件は、材料の種類、膜の目的とする結晶構造および会合構造などにより異なる。蒸着条件は一般的に、蒸着用ルツボの加熱温度+50~+400℃、真空度10-6~10-3Pa、蒸着速度0.01~50nm/秒、基板温度-150~+300℃、膜厚2nm~5μmの範囲で適宜設定することが好ましい。
また、本発明は、有機電界発光素子を備えた表示装置または有機電界発光素子を備えた照明装置などにも応用することができる。
有機電界発光素子を備えた表示装置または照明装置は、本実施形態にかかる有機電界発光素子と公知の駆動装置とを接続するなど公知の方法によって製造することができ、直流駆動、パルス駆動、交流駆動など公知の駆動方法を適宜用いて駆動することができる。
本発明に係る多環芳香族アミノ化合物は、上述した有機電界発光素子の他に、有機電界効果トランジスタまたは有機薄膜太陽電池などの作製に用いることができる。
(1)基板/ゲート電極/絶縁体層/ソース電極・ドレイン電極/有機半導体活性層
(2)基板/ゲート電極/絶縁体層/有機半導体活性層/ソース電極・ドレイン電極
(3)基板/有機半導体活性層/ソース電極・ドレイン電極/絶縁体層/ゲート電極
(4)基板/ソース電極・ドレイン電極/有機半導体活性層/絶縁体層/ゲート電極
このように構成された有機電界効果トランジスタは、アクティブマトリックス駆動方式の液晶ディスプレイや有機エレクトロルミネッセンスディスプレイの画素駆動スイッチング素子等として適用できる。
窒素雰囲気下、ジフェニルアミン(22.3g)、4-ブロモナフタレン-2-オール(28.0g)、Pd-132(ジョンソン・マッセイ)(0.9g)、NaOtBu(30.0g)およびトルエン(252ml)の入ったフラスコを加熱し、4時間還流した。反応液を室温まで冷却した後、水および酢酸エチルを加えて分液した。更にシリカゲルカラム(溶離液:トルエン)で精製し、中間体化合物の4-(ジフェニルアミノ)ナフタレン-2-オールを35g(収率:89.5%)得た。
窒素雰囲気下、4-(ジフェニルアミノ)ナフタレン-2-オール(16.0g)、2-ブロモ-1,3-ジフルオロベンゼン(5.0g)、炭酸カリウム(17.8g)および1-メチル-2-ピロリドン(30ml)の入ったフラスコを、還流温度で8時間加熱撹拌した。反応停止後、反応液を室温まで冷却し、水を加えて析出した沈殿物を吸引ろ過にて採取した。得られた沈殿物を水、次いでメタノールで洗浄した後、シリカゲルカラム(溶離液:へプタン/トルエン=2/1(容量比))で精製して、中間体化合物の3,3’-((2-ブロモ-1,3-フェニレン)ビス(オキシ))ビス(N,N-ジフェニルナフタレン-1-アミン)を15.2g(収率:76.2%)得た。
窒素雰囲気下、3,3’-((2-ブロモ-1,3-フェニレン)ビス(オキシ))ビス(N,N-ジフェニルナフタレン-1-アミン)(8.6g)およびテトラヒドロフラン(52ml)をフラスコに入れ、-40℃まで冷却し、1.6Mのn-ブチルリチウムヘキサン溶液(8ml)を滴下した。滴下終了後、この温度で1時間撹拌した後、トリメチルボレート(1.7g)を加えた。室温まで昇温して2時間撹拌した。その後、水(100ml)をゆっくり滴下した。次に、反応混合液を酢酸エチルで抽出し、無水硫酸ナトリウムで乾燥した後、乾燥剤を除去して、中間体化合物のジメチル(2,6-ビス((4-ジフェニルアミノ)ナフタレン-2-イル)オキシ)フェニル)ボロネートを8.5g(収率:99.4%)得た。
窒素雰囲気下、ジメチル(2,6-ビス((4-ジフェニルアミノ)ナフタレン-2-イル)オキシ)フェニル)ボロネート(7.9g)、塩化アルミニウム(AlCl3)(13.7g)およびクロロベンゼン(50ml)をフラスコに入れて5分間攪拌した。その後、N-エチルジイソプロピルアミン(16.7g)を加え、125℃で1時間加熱撹拌した。加熱終了後に反応液を冷却し、氷水(50ml)を添加した。その後、反応混合液をトルエンで抽出し、無水硫酸ナトリウムで乾燥した後、乾燥剤を除去し、溶媒を減圧留去して得られた粗製品をシリカゲルでカラム精製(溶離液:ヘプタン/トルエン=3/1(容量比))を行った後、ヘプタンで再沈殿を行った。次にNH2シリカゲルでカラム精製(溶離液:ヘプタン/トルエン=1/1(容量比))を行い、更に昇華精製をして、目的化合物(1A-1)を0.8g(収率:11%)得た。
1H-NMR(CDCl3):δ=8.00(d,2H)、7.88(d,2H)、7.70(t,1H)、7.47(s,2H)、7.31~7.22(m,12H)、7.18~7.16(m,8H)、7.09~7.04(m,6H).
窒素雰囲気下、4-(ジフェニルアミノ)ナフタレン-2-オール(16.1g)、5’-ブロモ-4’,6’-ジフルオロ-1,1’:3’,1”-テルフェニル(8.5g)、炭酸カリウム(13.6g)および1-メチル-2-ピロリドン(43ml)の入ったフラスコを、還流温度で3時間加熱撹拌した。反応停止後、反応液を室温まで冷却し、水を加えて析出した沈殿物を吸引ろ過にて採取した。得られた沈殿物を水、次いでメタノールで洗浄した後、シリカゲルショートカラム(溶離液:トルエン)で精製した。次に、酢酸エチルで再沈殿を行い、中間体化合物の3,3’-((5’-ブロモ-[1,1’:3’,1”-テルフェニル]-4’,6’-ジイル)ビス(オキシ))ビス(N,N-ジフェニルナフタレン-1-アミン)を22.6g(収率:98.9%)得た。
窒素雰囲気下、3,3’-((5’-ブロモ-[1,1’:3’,1”-テルフェニル]-4’,6’-ジイル)ビス(オキシ))ビス(N,N-ジフェニルナフタレン-1-アミン)(13.0g)およびキシレン(65ml)の入ったフラスコを-40℃まで冷却し、2.6Mのn-ブチルリチウムヘキサン溶液(6ml)を滴下した。滴下終了後、この温度で0.5時間撹拌した後、60℃まで昇温して2時間撹拌した。その後、反応液を減圧して低沸点の成分を留去した後、-40℃まで冷却して三臭化ホウ素(4.6g)を加えた。室温まで昇温して0.5時間撹拌した後、0℃まで冷却してN-エチルジイソプロピルアミン(4.0g)を添加し、125℃で5時間加熱撹拌した。反応液を室温まで冷却し、酢酸ナトリウム水溶液を加えて反応を停止させた後、トルエンを加えて分液した。有機層をシリカゲルショートパスカラム(溶離液:トルエン)、次いでシリカゲルカラム(溶離液:へプタン/トルエン=2/1(容量比))で精製した後、ヘプタンで再沈殿を行い、更に昇華精製をして、目的化合物(1A-173)を2.5g(収率:21%)得た。
1H-NMR(CDCl3):δ=8.00(d,2H)、7.91(s,1H)、7.89(d,2H)、7.78(dd,4H)、7.49(t,4H)、7.43(s,2H)、7.39(t,2H)、7.29~7.23(m,10H)、7.17~7.14(m,8H)、7.09~7.01(m,6H).
式(1A-153)の化合物:9-メチル-N5,N5,N13,N13-テトラフェニル-7,11-ジオキサ-17c-ボラフェナントロ[2,3,4-no]テトラフェン-5,13-ジアミンの合成
窒素雰囲気下、4-(ジフェニルアミノ)ナフタレン-2-オール(29.2g)、1,3-ジフルオロ-5-メチルベンゼン(6.0g)、リン酸三カリウム(49.7g)および1-メチル-2-ピロリドン(60ml)の入ったフラスコを還流温度で18時間加熱撹拌した。反応停止後、反応液を室温まで冷却し、水を加えて析出した沈殿物を吸引ろ過にて採取した。得られた沈殿物を水、次いでメタノールで洗浄した後、シリカゲルカラム(溶離液:トルエン/ヘプタン=1/2(容量比))で精製し、中間体化合物の3,3’-((5-メチル-1,3-フェニレン)ビス(オキシ))ビス(N,N-ジフェニルナフタレン-1-アミン)を20g(収率:60%)得た。
窒素雰囲気下、3,3’-((5-メチル-1,3-フェニレン)ビス(オキシ))ビス(N,N-ジフェニルナフタレン-1-アミン)(19.0g)およびキシレン(133ml)の入ったフラスコを0℃まで冷却し、1.6Mのn-ブチルリチウムヘキサン溶液(18.4ml)を滴下した。滴下終了後、この温度で0.5時間撹拌した後、80℃まで昇温して1時間撹拌した。その後、反応液を減圧して低沸点の成分を留去した後、-30℃まで冷却して三臭化ホウ素(10.0g)を加えた。室温まで昇温して0.5時間撹拌した後、0℃まで冷却してN-エチルジイソプロピルアミン(4.0g)を添加し、室温で10分間撹拌した。次に、塩化アルミニウム(7.1g)を加え、100℃で6時間加熱した。反応液を室温まで冷却し、酢酸カリウム水溶液を加えて反応を停止させた後、酢酸エチルを加えて分液した。有機層を無水硫酸ナトリウムで乾燥した後、乾燥剤を除去し、溶媒を減圧留去して得られた粗製品をNH2シリカゲルでカラム精製(溶離液:酢酸エチル→トルエン)を行った。次に、シリカゲルカラム(溶離液:トルエン/ヘプタン=1/3(容量比))で精製し、更に昇華精製をして、目的化合物(1A-153)を1.2g(収率:6%)得た。
1H-NMR(CDCl3):δ=8.00(d,2H)、7.89(d,2H)、7.45(s,2H)、7.30~7.16(m,18H)、7.08~7.03(m,8H)、2.55(s,3H).
式(1B-92)の化合物:7-([1,1’-ビフェニル]-4-イル)―(N,N,10-トリフェニル-7H-3-オキサ-7-アザ-11b-ボラフェナントロ[3,2,1-no]テトラフェン-1-アミンの合成
窒素雰囲気下、4-(ジフェニルアミノ)ナフタレン-2-オール(32.0g)、1-ブロモ-2-クロロ-3-フルオロベンゼン(23.7g)、炭酸カリウム(35.5g)および1-メチル-2-ピロリドン(160ml)の入ったフラスコを、還流温度で3時間加熱撹拌した。反応停止後、反応液を室温まで冷却し、水を加えて析出した沈殿物を吸引ろ過にて採取した。得られた沈殿物を水、次いでメタノールで洗浄した後、シリカゲルカラム(溶離液:トルエン/へプタン=1/5(容量比))で精製して、中間体化合物の3-(3-ブロモ-2-クロロフェノキシ)-N,N-ジフェニルナフタレン-1-アミンを46.5g(収率:90.3%)得た。
窒素雰囲気下、3-(3-ブロモ-2-クロロフェノキシ)-N,N-ジフェニルナフタレン-1-アミン(15.0g)、ジ([1,1’-ビフェニル]-4-イル)アミン(9.6g)、Pd-132(ジョンソン・マッセイ)(0.64g)、NaOtBu(7.2g)およびキシレン(75ml)の入ったフラスコを100℃で2時間加熱した。反応液を室温まで冷却した後、水およびトルエンを加えて分液した。更にシリカゲルカラム(溶離液:トルエン/へプタン=1/2(容量比))で精製して、中間体化合物の3-(2-クロロ-3-(ジ([1,1’-ビフェニル]-4-イル)アミノ)フェノキシ)-N,N-ジフェニルナフタレン-1-アミンを19.6g(収率:88.3%)を得た。
窒素雰囲気下で、3-(2-クロロ-3-(ジ([1,1’-ビフェニル]-4-イル)アミノ)フェノキシ)-N,N-ジフェニルナフタレン-1-アミン(4.0g)およびキシレン(30ml)の入ったフラスコを0℃まで冷却した後、2.6Mのn-ブチルリチウムのn-ヘキサン溶液(4.2ml)を加えた。70℃まで昇温し、1時間撹拌した。その後、フラスコを-20℃まで冷却し、2-イソプロポキシ-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン(iPrO-BPin)(3.0g)を加え、室温で2時間攪拌した後、水およびトルエンを加えて分液した。更にシリカゲルカラム(溶離液:トルエン/へプタン=1/1(容量比))で精製して、中間体化合物の4-(3-(ジ([1,1’-ビフェニル]-4-イル)アミノ)-2-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)フェノキシ)-N,N-ジフェニルナフタレン-1-アミンを3.1g(収率:69.0%)得た。
4-(3-(ジ([1,1’-ビフェニル]-4-イル)アミノ)-2-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)フェノキシ)-N,N-ジフェニルナフタレン-1-アミン(0.8g)、塩化アルミニウム(1.3g)およびトルエン(8ml)をフラスコに入れて3分間攪拌した。その後、N-エチルジイソプロピルアミン(0.25g)を加え、120℃で2時間撹拌した。加熱終了後に反応液を冷却した後、氷浴で冷却しながら、反応液を氷水(20ml)と酢酸エチル(20ml)との混合溶液に加え、30分間攪拌した。その後、反応混合液の有機層をシリカゲルショートパスカラム(溶離液:トルエン)、次いでシリカゲルカラム(溶離液:トルエン/へプタン=1/2(容量比))で精製した。さらに、NH2シリカゲルでカラム精製(溶離液:トルエン/ヘプタン=2/1(容量比))を行い、目的化合物(1B-92)を0.1g(収率:14.5%)得た。
1H-NMR(CDCl3):δ=9.10(d,1H)、8.92(s,1H)、8.04(d,1H)、7.96(d,2H)、7.78~7.73(m,3H)、7.66(d,2H)、7.56~7.37(m,10H)、7.29~7.24(m,5H)、7.17~7.15(m,5H)、7.05~7.01(m,4H)、6.52(d,1H).
式(1A-1)、式(1A-173)、式(1A-153)で表される化合物および比較例の化合物の蛍光量子収率を測定した。蛍光量子収率測定は、評価対象の化合物を市販のPMMA(ポリメチルメタクリレート)樹脂に分散後、薄膜化して評価する手法にて行った。
実施例1~3および比較例1~11に係る有機EL素子を作製し、それぞれ1000cd/m2発光時の特性である電圧(V)、EL発光波長(nm)および外部量子効率(%)の測定し、次に10mA/cm2の電流密度で定電流駆動した際の初期輝度の90%以上の輝度を保持する時間を測定した。
<化合物(1A-173)を発光層のドーパントに用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HI、HAT-CN、HT、BH1、本発明の化合物(1A-173)、ET5およびET6のぞれぞれを入れたタンタル製蒸着用ルツボ、Liq、マグネシウムおよび銀のそれぞれを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<化合物(1A-173)を発光層のドーパントに用いた素子>
発光層において、BH1と本発明の化合物(1A-173)の重量比をおよそ95対5になるように蒸着速度を調節した以外は実施例1に準じた方法で有機EL素子を得た。同様に特性を測定すると、駆動電圧は3.95V、外部量子効率は6.7%(波長約470nmの青色発光)であり、その時のCIE色度は(x,y)=(0.122,0.181)であった。また、初期輝度の90%以上の輝度を保持する時間は270時間であった。
<化合物(1A-1)を発光層のドーパントに用いた素子>
発光層のドーパントである化合物(1A-173)を化合物(1A-1)に替えた以外は実施例1に準じた方法で有機EL素子を得た。同様に特性を測定すると、駆動電圧は4.25V、外部量子効率は6.0%(波長約465nmの青色発光)であり、その時のCIE色度は(x,y)=(0.128,0.143)であった。また、初期輝度の90%以上の輝度を保持する時間は180時間であった。
<公知化合物(1-10)を発光層のドーパントに用いた素子>
<公知化合物(1-100)を発光層のドーパントに用いた素子>
<公知化合物(1-141)を発光層のドーパントに用いた素子>
<公知化合物(1-176)を発光層のドーパントに用いた素子>
<公知化合物(1-447)を発光層のドーパントに用いた素子>
<公知化合物(1-401)を発光層のドーパントに用いた素子>
<公知化合物(1-1201)を発光層のドーパントに用いた素子>
<公知化合物(1-1210)を発光層のドーパントに用いた素子>
<公知化合物(1-79)を発光層のドーパントに用いた素子>
<公知化合物(1-1006)を発光層のドーパントに用いた素子>
<公知化合物(1-2305)を発光層のドーパントに用いた素子>
実施例4および比較例12に係る有機EL素子を作製し、それぞれ1000cd/m2発光時の特性である電圧(V)、EL発光波長(nm)および外部量子効率(%)の測定し、次に10mA/cm2の電流密度で定電流駆動した際の初期輝度の90%以上の輝度を保持する時間を測定した。
<化合物(1A-153)を発光層のドーパントに用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HI、HAT-CN、HT、BH1、本発明の化合物(1A-153)、ET5およびET6のぞれぞれを入れたタンタル製蒸着用ルツボ、Liq、マグネシウムおよび銀のそれぞれを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<公知化合物(1-2680)を発光層のドーパントに用いた素子>
実施例5および比較例13に係る有機EL素子を作製し、それぞれ1000cd/m2発光時の特性である電圧(V)、EL発光波長(nm)および外部量子効率(%)の測定し、次に10mA/cm2の電流密度で定電流駆動した際の初期輝度の90%以上の輝度を保持する時間を測定した。
<化合物(1A-1)を発光層のドーパントに用いた素子>
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)長州産業)の基板ホルダーに固定し、HI、HAT-CN、HT、HT2、BH2、本発明の化合物(1A-1)、ET7およびET8のそれぞれを入れたタンタル製蒸着用ルツボ、Liq、マグネシウムおよび銀のそれぞれを入れた窒化アルミニウム製蒸着用ルツボを装着した。
<公知化合物(1-1152)を発光層のドーパントに用いた素子>
101 基板
102 陽極
103 正孔注入層
104 正孔輸送層
105 発光層
106 電子輸送層
107 電子注入層
108 陰極
Claims (18)
- 下記一般式(1A)または一般式(1B)で表される多環芳香族アミノ化合物。
Arは、それぞれ独立して、アリールまたはヘテロアリールであり、
R1~R4は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシ、トリアルキルシリル、アリールオキシまたはシアノであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノまたはアルキルで置換されていてもよく、
R4が複数の場合、隣接するR4同士は結合してa環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシ、トリアルキルシリル、アリールオキシまたはシアノで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノまたはアルキルで置換されていてもよく、
R1とR3が隣接する場合には、これらは-O-、-S-、-C(-R)2-または単結合により結合していてもよく、前記-C(-R)2-のRは水素または炭素数1~6のアルキルであり、
mは0~3の整数であり、nはそれぞれ独立して0からArに最大置換可能な数までの整数であり、pは0~4の整数であり、qはそれぞれ独立して0~5の整数であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルであり、また、X2が前記N-Rである場合のRは-O-、-S-、-C(-R)2-または単結合により前記a環と結合していてもよく、前記-C(-R)2-のRは水素または炭素数1~6のアルキルであり、そして、
式(1A)または式(1B)で表される化合物における少なくとも1つの水素はハロゲンまたは重水素で置換されていてもよい。) - Arは、それぞれ独立して、アリールであり、
R2~R4は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
R4が複数の場合、隣接するR4同士は結合してa環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
mは0~3の整数であり、nはそれぞれ独立して0からArに最大置換可能な数までの整数であり、pは0~4の整数であり、qは0であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルである、
請求項1に記載する多環芳香族アミノ化合物。 - 下記一般式(1A’)または一般式(1B’)で表される、請求項1に記載する多環芳香族アミノ化合物。
R2~R4は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
R4が複数の場合、隣接するR4同士は結合してa環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、アルキル、アルコキシ、トリアルキルシリルまたはアリールオキシで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
mは0~3の整数であり、nはそれぞれ独立して0~5の整数であり、pは0~4の整数であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルである。) - 下記一般式(1A’)で表される、請求項1に記載する多環芳香族アミノ化合物。
R2およびR3は、それぞれ独立して、水素、炭素数6~30のアリール、炭素数2~30のヘテロアリール、炭素数6~30のジアリールアミノ、炭素数1~24のアルキル、炭素数1~24のアルコキシ、炭素数1~4のアルキルを有するトリアルキルシリルまたは炭素数6~30のアリールオキシであり、これらにおける少なくとも1つの水素は炭素数6~16のアリール、炭素数2~25のヘテロアリールまたは炭素数1~18のアルキルで置換されていてもよく、
mは0~3の整数であり、nはそれぞれ独立して0~5の整数であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~10のアリール、炭素数2~10のヘテロアリールまたは炭素数1~4のアルキルである。) - R2およびR3は、それぞれ独立して、水素、炭素数6~30のアリール、炭素数2~30のヘテロアリール、炭素数1~24のアルキルまたは炭素数1~4のアルキルを有するトリアルキルシリルであり、
mは0または1であり、nはそれぞれ独立して0または1であり、
X1およびX2は、それぞれ独立して、OまたはN-Rであり、前記N-RのRは炭素数6~10のアリール、炭素数2~10のヘテロアリールまたは炭素数1~4のアルキルである、
請求項4に記載する多環芳香族アミノ化合物。 - 請求項1~6のいずれかに記載する多環芳香族アミノ化合物を含有する、有機デバイス用材料。
- 前記有機デバイス用材料が、有機電界発光素子用材料、有機電界効果トランジスタ用材料または有機薄膜太陽電池用材料である、請求項7に記載する有機デバイス用材料。
- 発光層用材料である、請求項8に記載する有機電界発光素子用材料。
- 電子注入層用材料または電子輸送層用材料である、請求項8に記載する有機電界発光素子用材料。
- 正孔注入層用材料または正孔輸送層用材料である、請求項8に記載する有機電界発光素子用材料。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置され、請求項9に記載する発光層用材料を含有する発光層とを有する、有機電界発光素子。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置された発光層と、前記陰極および前記発光層の間に配置され、請求項10に記載する電子注入層用材料および/または電子輸送層用材料を含有する電子注入層および/または電子輸送層とを有する、有機電界発光素子。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置された発光層と、前記陽極および前記発光層の間に配置され、請求項11に記載する正孔注入層用材料および/または正孔輸送層用材料を含有する正孔注入層および/または正孔輸送層とを有する、有機電界発光素子。
- 前記陰極と該発光層との間に配置される電子輸送層および/または電子注入層を有し、該電子輸送層および電子注入層の少なくとも1つは、キノリノール系金属錯体、ピリジン誘導体、フェナントロリン誘導体、ボラン誘導体およびベンゾイミダゾール誘導体からなる群から選択される少なくとも1つを含有する、請求項12~14のいずれかに記載する有機電界発光素子。
- 前記電子輸送層および/または電子注入層が、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、請求項15に記載の有機電界発光素子。
- 請求項12~16のいずれかに記載する有機電界発光素子を備えた表示装置。
- 請求項12~16のいずれかに記載する有機電界発光素子を備えた照明装置。
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KR1020197011911A KR102438956B1 (ko) | 2016-12-16 | 2017-12-11 | 다환방향족 아미노 화합물 |
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WO2020109039A1 (en) | 2018-11-28 | 2020-06-04 | Basf Se | Pesticidal compounds |
WO2020149663A1 (ko) * | 2019-01-18 | 2020-07-23 | 주식회사 엘지화학 | 유기 발광 소자 |
WO2021219513A1 (en) | 2020-04-28 | 2021-11-04 | Basf Se | Pesticidal compounds |
WO2023282676A1 (ko) | 2021-07-07 | 2023-01-12 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
US11903310B2 (en) | 2019-11-05 | 2024-02-13 | Samsung Display Co., Ltd. | Organic light-emitting device and method of manufacturing the same |
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WO2018203666A1 (ko) * | 2017-05-02 | 2018-11-08 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
US11532794B2 (en) * | 2019-10-28 | 2022-12-20 | Samsung Display Co., Ltd. | Compound and light-emitting device including the same |
KR20210068229A (ko) * | 2019-11-29 | 2021-06-09 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 아민 화합물 |
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WO2023282676A1 (ko) | 2021-07-07 | 2023-01-12 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
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CN110049990A (zh) | 2019-07-23 |
JPWO2018110497A1 (ja) | 2019-10-24 |
JP7083132B2 (ja) | 2022-06-10 |
KR20190096944A (ko) | 2019-08-20 |
US20200020859A1 (en) | 2020-01-16 |
KR102438956B1 (ko) | 2022-08-31 |
CN110049990B (zh) | 2022-09-13 |
US11539003B2 (en) | 2022-12-27 |
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