WO2019074093A1 - Polycyclic aromatic dimeric compound - Google Patents
Polycyclic aromatic dimeric compound Download PDFInfo
- Publication number
- WO2019074093A1 WO2019074093A1 PCT/JP2018/038086 JP2018038086W WO2019074093A1 WO 2019074093 A1 WO2019074093 A1 WO 2019074093A1 JP 2018038086 W JP2018038086 W JP 2018038086W WO 2019074093 A1 WO2019074093 A1 WO 2019074093A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ring
- carbon atoms
- aryl
- substituted
- carbons
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 149
- 239000000463 material Substances 0.000 claims abstract description 160
- 125000003118 aryl group Chemical group 0.000 claims abstract description 144
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 126
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 100
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 93
- 125000005647 linker group Chemical group 0.000 claims abstract description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 125000000732 arylene group Chemical group 0.000 claims abstract description 15
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 12
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 11
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- -1 quinolinol metal complex Chemical class 0.000 claims description 123
- 238000002347 injection Methods 0.000 claims description 70
- 239000007924 injection Substances 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 239000000539 dimer Substances 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 229910052782 aluminium Inorganic materials 0.000 claims description 30
- 239000010409 thin film Substances 0.000 claims description 30
- 229910052698 phosphorus Inorganic materials 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 150000001340 alkali metals Chemical class 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000004986 diarylamino group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 229910052796 boron Inorganic materials 0.000 claims description 14
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 13
- 150000002910 rare earth metals Chemical class 0.000 claims description 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 230000005669 field effect Effects 0.000 claims description 10
- 229910052733 gallium Inorganic materials 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052785 arsenic Inorganic materials 0.000 claims description 8
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 5
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 3
- 238000005286 illumination Methods 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004431 deuterium atom Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 244
- 239000011799 hole material Substances 0.000 description 60
- 229910052757 nitrogen Inorganic materials 0.000 description 56
- 230000032258 transport Effects 0.000 description 51
- 239000000758 substrate Substances 0.000 description 44
- 125000001424 substituent group Chemical group 0.000 description 38
- 230000005525 hole transport Effects 0.000 description 33
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002019 doping agent Substances 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000010408 film Substances 0.000 description 20
- 230000005284 excitation Effects 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 14
- 239000004065 semiconductor Substances 0.000 description 14
- 238000000151 deposition Methods 0.000 description 13
- 230000008021 deposition Effects 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 11
- 239000012043 crude product Substances 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 10
- 229910052792 caesium Inorganic materials 0.000 description 9
- 150000004775 coumarins Chemical class 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 8
- 239000004926 polymethyl methacrylate Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000002904 solvent 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 238000001296 phosphorescence spectrum Methods 0.000 description 6
- 239000010453 quartz Substances 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000007983 Tris buffer 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
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 5
- 230000004888 barrier function Effects 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
- 230000003111 delayed effect Effects 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000005281 excited state Effects 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 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
- 239000000047 product Substances 0.000 description 5
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 5
- 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 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000001556 benzimidazoles Chemical class 0.000 description 4
- 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 4
- 239000004305 biphenyl Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012212 insulator Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 150000004880 oxines Chemical class 0.000 description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 4
- 238000005424 photoluminescence Methods 0.000 description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 125000005504 styryl group Chemical group 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 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
- 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 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 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 239000000706 filtrate Substances 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
- 238000010438 heat treatment Methods 0.000 description 3
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
-
- 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
-
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
Definitions
- the present invention relates to a polycyclic aromatic dimer compound, an organic electroluminescent device using the same, an organic field effect transistor, an organic thin film solar cell, a display device and a lighting device.
- display devices using light emitting elements that emit light by electroluminescence are variously studied because they can be reduced in power and thickness, and organic electroluminescent elements made of organic materials can be easily reduced in weight and size. It has been actively considered from that.
- the organic EL element has a structure comprising a pair of electrodes comprising an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing an organic compound.
- Layers containing an organic compound include a light emitting layer, and a charge transport / injection layer that transports or injects a charge such as a hole or an electron, and various organic materials suitable for these layers have been developed.
- benzofluorene compounds and the like As materials for light emitting layers, for example, benzofluorene compounds and the like have been developed (WO 2004/061047).
- a hole transport material for example, triphenylamine compounds and the like have been developed (Japanese Patent Laid-Open No. 2001-172232).
- an electron transport material for example, an anthracene compound and the like have been developed (Japanese Patent Laid-Open No. 2005-170911).
- a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence of a shorter wavelength, and thus is useful as a material for a blue light emitting layer.
- a compound having a novel conjugated structure with a large T1 is also required as an electron transporting material and a hole transporting material sandwiching the light emitting layer.
- the host material of the organic EL element is a molecule in which existing aromatic rings such as benzene and carbazole are linked by a plurality of single bonds, phosphorus atoms or silicon atoms. This is because connecting a large number of relatively small conjugated aromatic rings ensures a large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material. Furthermore, although a high triplet excitation energy (E T ) is also required for a host material of an organic EL element using a phosphorescent material or a thermally activated delayed fluorescence material, an aromatic ring or a substituent having donor or acceptor properties for the molecule is required.
- E T triplet excitation energy
- the present inventors have made it possible to obtain better organic substances by dimerizing a polycyclic aromatic compound in which a plurality of aromatic rings are linked by a boron atom and an oxygen atom. They found that they could be materials for devices, and completed the present invention. That is, the present invention provides the following polycyclic aromatic dimer compounds, as well as materials for organic EL devices including the dimer compounds.
- a dimer compound comprising two partial structures represented by the following general formula (1) and a linking group L1 linking the two partial structures, (In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
- the partial structure represented by formula (1) may have the same structure or different structures from each other, provided that in the two partial structures, Y 1 is both B and X 1 and X 2 are both> The case of O is excluded, and the case where Y 1 is both P ⁇ ⁇ O, X 1 and X 2 are both> O is also excluded.
- the linking group L 1 is a single bond, arylene having 6 to 30 carbon atoms, heteroarylene having 2 to 30 carbon atoms, alkylene having 1 to 24 carbon atoms, alkenylene having 1 to 24 carbon atoms, alkynylene having 1 to 24 carbon atoms, -R-, -S-,> N-R, or a combination thereof, wherein R in> N-R is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, or 1 to carbon atoms 12 alkyl or cycloalkyl having 3 to 16 carbon atoms, at least one hydrogen in the linking group L 1 is aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, alkyl or 1 to 12 carbons And may be substituted with 3 to 16 cycloalkyls,
- the dimer compound in which at least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
- Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted
- the ring may be substituted with unsubstituted aryloxy, and these rings may be 5- or 6-membered rings sharing a bond with the fused two-ring structure at the center of the above formula composed of Y 1 , X 1 and X 2 Have a ring, Y 1 is
- the linking group L 1 is a single bond, arylene having 6 to 16 carbon atoms, heteroarylene having 2 to 20 carbon atoms, alkylene having 1 to 12 carbon atoms, alkenylene having 1 to 12 carbon atoms, alkynylene having 1 to 12 carbon atoms, -R-, -S-,> N-R, or a combination thereof, wherein R in> N-R is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, or 1 to carbons 6 alkyl or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the linking group L 1 is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl or 1 to 6 carbons And may be substituted with several 3 to 14 cycloalkyls, At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
- Item 1 is a dimer compound.
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylamino Heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and R 1 to Adjacent groups of R 11 may combine to form an aryl ring or heteroaryl ring with the a ring, b ring or c ring, and at least one hydrogen in the formed ring is aryl, heteroaryl , Diarylamino, diheteroarylamino, arylheteroarylamino
- the linking group L 1 is a single bond, arylene having 6 to 12 carbon atoms, heteroarylene having 2 to 15 carbon atoms, alkylene having 1 to 6 carbon atoms, alkenylene having 1 to 6 carbon atoms, alkynylene having 1 to 6 carbon atoms, -R-, -S-,> N-R, or a combination thereof, wherein R in> N-R is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, or 1 to carbons 6 alkyl or cycloalkyl having 3 to 14 carbon atoms, At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
- Item 1 is a dimer compound described in any one of the following chemical structures.
- Item 6 A material for an organic device, comprising the dimer compound according to any one of Items 1 to 5.
- Item 7. The organic device material according to item 6, wherein the organic device material is an organic electroluminescent device material, an organic field effect transistor material, or an organic thin film solar cell material.
- Item 8. A material for an organic electroluminescent device according to item 7, which is a material for a light emitting layer.
- Item 9 An organic electroluminescent device comprising: a pair of electrodes consisting of an anode and a cathode; and a light emitting layer disposed between the pair of electrodes and containing the material for a light emitting layer described in item 8.
- Item 10 It has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer comprises a quinolinol metal complex, a pyridine derivative, a phenanthroline derivative Item 10.
- the electron transport layer and / or the electron injection layer may further be selected from alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, and alkaline earth metals.
- Item 10 containing at least one selected from the group consisting of halides, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals
- the organic electroluminescent element as described in.
- Item 12. A display device or lighting device comprising the organic electroluminescent device according to any one of items 9 to 11.
- an excellent polycyclic aromatic dimer compound which can be used, for example, as a material for an organic EL element can be provided, and the use of this dimer compound is excellent.
- An organic device such as an organic EL element can be provided.
- a dimer of a polycyclic aromatic compound in which an aromatic ring is linked by a hetero element such as boron, phosphorus, oxygen, nitrogen, or sulfur is a large HOMO-LUMO gap (a band in a thin film It was found to have a gap Eg) and high triplet excitation energy (E T ).
- Eg triplet excitation energy
- T1 triplet excited state
- the polycyclic aromatic dimer compound containing a hetero element according to the present invention has a smaller exchange interaction between both orbitals due to the localization of SOMO1 and SOMO2 in the triplet excited state (T1). Since the energy difference between the triplet excited state (T1) and the singlet excited state (S1) is small and thermally activated delayed fluorescence is exhibited, it is also useful as a fluorescent material of an organic EL element. In addition, a material having 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 dimer compounds can move the energy of HOMO and LUMO arbitrarily by introducing a substituent, the ionization potential and the electron affinity should be optimized according to the surrounding materials. Is possible.
- the dimer compound of this invention can anticipate fall of melting
- sublimation purification which is almost indispensable as a purification method for materials for organic devices such as organic EL elements that require high purity
- purification can be performed at a relatively low temperature, so that thermal decomposition of the material is avoided.
- vacuum deposition process which is an effective means for producing organic devices such as organic EL elements, and the process can be performed at a relatively low temperature, so thermal decomposition of the material can be avoided.
- high performance organic devices can be obtained.
- the solubility in an organic solvent is improved by the introduction of a cycloalkyl group, the present invention can be applied to device fabrication using a coating process.
- the present invention is not particularly limited to these principles.
- the present invention is a dimer compound comprising two partial structures represented by the following general formula (1) and a linking group L1 linking the two partial structures.
- the present invention is preferably a dimer compound comprising two partial structures represented by the following general formula (2) and a linking group L1 linking the two partial structures.
- symbol in all the structural formulas used by subsequent description is the same as the definition mentioned above.
- the ring A, ring B and ring C in the general formula (1) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted by a substituent.
- This substituent is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (aryl and An amino group having a heteroaryl), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy is preferable.
- substituents include aryl, heteroaryl, alkyl and cycloalkyl.
- substituents include aryl, heteroaryl, alkyl and cycloalkyl.
- the aryl ring or heteroaryl ring is bonded to a fused two-ring structure at the center of the general formula (1) composed of Y 1 , X 1 and X 2 (hereinafter, this structure is also referred to as “D structure”) It is preferable to have a shared 5- or 6-membered ring.
- fused 2-ring structure refers to a fused two saturated hydrocarbon ring composed of Y 1 , X 1 and X 2 shown at the center of the general formula (1) Means the structure.
- a six-membered ring sharing a bond with a fused two-ring structure means, for example, the a ring (benzene ring (six-membered ring)) fused to the D structure as shown in the general formula (2) above.
- an aryl ring or heteroaryl ring (which is a ring A) has this six-membered ring” means that only this six-membered ring forms an A ring or that it includes this six-membered ring.
- an aryl ring or heteroaryl ring having a 6-membered ring (A ring) having a 6-membered ring” referred to herein means a 6-membered ring constituting all or part of the A ring fused to the D structure.
- a ring aryl ring or heteroaryl ring having a 6-membered ring having a 6-membered ring
- B ring (b ring) means a 6-membered ring constituting all or part of the A ring fused to the D structure.
- Ring A (or ring B, ring C) in the general formula (1) is the ring a in the general formula (2) and its substituents R 1 to R 3 (or ring b and its substituents R 8 to R 11 , c It corresponds to the ring and its substituents R 4 to R 7 ). That is, General Formula (2) corresponds to a structural formula in which “A to C ring having a 6-membered ring” is selected as the A to C ring of General Formula (1). In that sense, each ring of the general formula (2) is represented by a to c in lower case.
- adjacent groups among the substituents R 1 to R 11 in the a ring, b ring and c ring are combined to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring.
- at least one hydrogen in the ring formed may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy
- at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
- the partial structure represented by the general formula (2) can be represented by the following formulas (2-1) and (2-2) depending on the mutual bonding form of the substituents in the a ring, b ring and c ring:
- the ring structure constituting the partial structure changes.
- the ring A ′, the ring B ′ and the ring C ′ in each formula correspond to the ring A, the ring B and the ring C in the general formula (1), respectively.
- the ring A ′, the ring B ′ and the ring C ′ in the above formula (2-1) and the formula (2-2) may be adjacent to one of the substituents R 1 to R 11 if it is described in the general formula (2) Groups are bonded to each other to represent an aryl ring or a heteroaryl ring formed together with the a ring, b ring and c ring (a fused ring formed by condensation of another ring structure to the a ring, b ring or c ring It can be said that).
- R 8 in the b ring and R 7 in the c ring, R 11 in the b ring and R 1 in the a ring, c ring R 4 and R 3 in the a ring do not correspond to “adjacent groups” and these are not bonded. That is, "adjacent group” means an adjacent group on the same ring.
- the partial structure represented by the above formula (2-1) or formula (2-2) may be represented by, for example, the formula (1-9) or formula (1-99) listed as specific compounds described later.
- the fused ring A ′ (or fused ring B ′ or fused ring C ′) which is a partial structure having a ring or C ′ ring) and is formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene, respectively It is a ring etc.
- P O
- P S, Si—R or Ge—R
- the atom bonded to the A ring, B ring or C ring is P, Si or Ge.
- X 1 and X 2 in the general formula (1) are each independently>O,>N—R,> S or> Se, and in the above> N—R, R is optionally substituted aryl, Optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, wherein R in> N—R represents a ring, ring B and / or ring C depending on the linking group L 2
- the linking group L2 may be bonded to a ring, and a single bond, -O-, -S- or -C (-R) 2 -is preferable.
- R of the above-mentioned "-C (-R) 2- " is hydrogen, alkyl or cycloalkyl. This description is the same for X 1 and X 2 in the general formula (2).
- R in> N—R is bonded to the ring A, ring B and / or ring C via a linking group L2
- R in> NR is connected to the a ring, b ring and / or c ring via a linking group L2 selected from —O—, —S—, —C (—R) 2 — and a single bond
- This definition can be expressed by a partial structure represented by the following formula (2-3-1), which has a ring structure in which X 1 or X 2 is incorporated into fused ring B ′ and fused ring C ′.
- the B ′ ring (or the ring formed by condensation of other rings such that X 1 (or X 2 ) is incorporated into the benzene ring which is ring b (or ring c) in the general formula (2) A compound having a C 'ring).
- the fused ring B '(or fused ring C') formed and formed is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
- the above definition is a moiety represented by the following formula (2-3-2) or (2-3-3) and having a ring structure in which X 1 and / or X 2 is incorporated into the fused ring A ′ It can also be expressed by structure. That is, for example, it is a partial structure having an A ′ ring formed by condensing other rings with X 1 (and / or X 2 ) being incorporated into a benzene ring which is a ring in the general formula (2) is there.
- the fused ring A 'formed and formed is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
- Examples of the “aryl ring” which is ring A, ring B and ring C in the general formula (1) include an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, The aryl ring of 6 to 12 is more preferable, and the aryl ring of 6 to 10 carbon atoms is particularly preferable.
- this "aryl ring” is defined by the general formula (2) as "an aryl ring formed by bonding adjacent groups of R 1 to R 11 together with the a ring, b ring or c ring"
- the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total number of carbons 9 in the fused ring in which the 5-membered ring is fused is a lower limit carbon It becomes a number.
- aryl ring examples include a benzene ring which is a monocyclic ring, a biphenyl ring which is a bicyclic ring, a naphthalene ring which is a fused bicyclic ring, and a terphenyl ring which is a tricyclic ring (m-terphenyl, o -Terphenyl, p-terphenyl), fused tricyclic ring, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, fused tetracyclic ring triphenylene ring, pyrene ring, naphthacene ring, fused pentacyclic ring Perylene ring, pentacene ring and the like can be mentioned.
- heteroaryl ring which is ring A, ring B and ring C in the general formula (1)
- examples of the “heteroaryl ring” include a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms And a heteroaryl ring having 2 to 20 carbon atoms is more preferable, a heteroaryl ring having 2 to 15 carbon atoms is more preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable.
- a heterocyclic ring containing 1 to 5 hetero atoms selected from oxygen, sulfur and nitrogen in addition to carbon as a ring constituting atom can be mentioned.
- this “heteroaryl ring” is a heteroaryl defined by the general formula (2), in which “adjacent groups of R 1 to R 11 are combined with each other to form a ring, b ring or c ring.
- the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total carbon number 6 of the fused ring in which a 5-membered ring is fused is the lower limit The carbon number of
- heteroaryl ring includes, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring , Cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring
- At least one hydrogen in the above “aryl ring” or “heteroaryl ring” is the first substituent, substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted "Diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted Although it may be substituted by unsubstituted "alkoxy” or substituted or unsubstituted "aryloxy”, aryl of "aryl", “heteroaryl” or “diarylamino” as this first substituent , “Diheteroarylamino” heteroaryl, “arylheteroarylamino” aryl and Lumpur, also is a
- alkyl as the first substituent may be either 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 (C3-C6 branched alkyl) is more preferable, and C1-C4 alkyl (C3-C4 branched alkyl) 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,
- the “cycloalkyl” as the first substituent includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and cycloalkyl having 3 to 14 carbon atoms. And cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and the like.
- cycloalkyl cyclopropyl, methylcyclopropyl, cyclobutyl, methylcyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, cycloheptyl, methylcycloheptyl, cyclooctyl, methylcyclooctyl, cyclononyl, methylcyclononyl , Cyclodecyl, methylcyclodecyl, bicyclo [1.0.1] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, bicyclo [1.2.1] hexyl, bicyclo [3 And 0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroa
- alkoxy as the first substituent includes, for example, linear or branched alkoxy having 1 to 24 carbon atoms.
- C1-C18 alkoxy (branched alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbons (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and C1 to 6 carbons are preferable.
- C1 to 6 carbons are preferable.
- alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.
- the first substituent substituted or unsubstituted "aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted Or unsubstituted "arylheteroarylamino", substituted or unsubstituted "alkyl”, substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy”
- a second substituent as is described as being substituted or unsubstituted.
- the second substituent includes, for example, aryl, heteroaryl, alkyl or cycloalkyl, and specific examples thereof include the monovalent groups of the “aryl ring” or “heteroaryl ring” described above, See also the description of "alkyl” or "cycloalkyl” as the first substituent.
- aryl and heteroaryl as the second substituent at least one hydrogen thereof is aryl such as phenyl (specific examples are the above-mentioned groups), alkyl such as methyl (specific examples are the above-mentioned groups) and cyclohexyl And the like.
- a group substituted with a cycloalkyl is also included in aryl and heteroaryl as the second substituent.
- the second substituent is a carbazolyl group
- the carbazolyl group in which at least one hydrogen at position 9 is substituted with an aryl such as phenyl or an alkyl such as methyl or a cycloalkyl such as cyclohexyl is also a second Is included in heteroaryl as a substituent of
- the aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino or aryloxy of aryloxy in R 1 to R 11 of the general formula (2) have a general formula Examples thereof include monovalent groups of the "aryl ring" or the "heteroaryl ring” described in (1).
- alkyl, cycloalkyl or alkoxy in R 1 to R 11 refer to the descriptions of “alkyl”, “cycloalkyl” and “alkoxy” as the first substituent in the description of the general formula (1) described above. can do.
- aryl, heteroaryl, alkyl or cycloalkyl as a substituent to these groups are also the same.
- heteroaryl which is a substituent to these rings when adjacent groups among R 1 to R 11 are combined to form an aryl ring or a heteroaryl ring with the a ring, b ring or c ring.
- R in Si—R and Ge—R in Y 1 in General Formula (1) is an aryl, an alkyl or a cycloalkyl, and examples of the aryl, an alkyl or a cycloalkyl include the groups described above.
- aryl having 6 to 10 carbon atoms eg, phenyl, naphthyl etc.
- alkyl having 1 to 4 carbon atoms eg methyl, ethyl etc.
- R> N—R in X 1 and X 2 of the general formula (1) is aryl, heteroaryl, alkyl or cycloalkyl which may be substituted with the above-mentioned second substituent, aryl, heteroaryl, At least one hydrogen in alkyl or cycloalkyl may be substituted, for example, by alkyl or cycloalkyl.
- the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above.
- aryl having 6 to 10 carbons such as phenyl and naphthyl
- heteroaryl having 2 to 15 carbons such as carbazolyl
- alkyl having 1 to 4 carbons such as methyl and ethyl
- 3 to 16 carbons Preferred are cycloalkyls such as bicyclooctyl and adamantyl. This description is the same for X 1 and X 2 in the general formula (2).
- R of “—C (—R) 2 —” which is a linking group L 2 in the general formula (1) is hydrogen, alkyl or cycloalkyl, and examples of the alkyl or cycloalkyl include the groups described above. In particular, alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl etc.) is preferable. This description is the same as “—C (—R) 2 —” which is the linking group L 2 in the general formula (2).
- the compound of the present invention is a compound in which two partial structures represented by formula (1) are linked via a linking group L1, but the two partial structures may have the same or different structures. , Preferably the same structure. However, if Y 1 is both B and X 1 and X 2 are both> O in two partial structures, it is excluded from the present invention and Y 1 is both PPO, both X 1 and X 2 are> The case of O is also excluded from the present invention.
- the linking group L 1 is a single bond, arylene having 6 to 30 carbon atoms, heteroarylene having 2 to 30 carbon atoms, alkylene having 1 to 24 carbon atoms, alkenylene having 1 to 24 carbon atoms, alkynylene having 1 to 24 carbon atoms, O-, -S-,> N-R, or a combination thereof.
- R in the above> N—R is aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, alkyl having 1 to 12 carbons or cycloalkyl having 3 to 16 carbons.
- At least one hydrogen in the linking group L1 may be substituted with aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, alkyl having 1 to 12 carbons or cycloalkyl having 3 to 16 carbons.
- arylene As for “arylene”, “heteroarylene” and “alkylene” in the linking group L1, the explanation of “aryl”, “heteroaryl” and “alkyl” at the position of the partial structure of the formula (1) is described as a divalent group It can be quoted instead of the explanation.
- the linking group L 1 is an arylene having 6 to 30 carbon atoms, a heteroarylene having 2 to 30 carbon atoms, an alkylene having 1 to 24 carbon atoms, an alkenylene having 1 to 24 carbon atoms, an alkynylene having 1 to 24 carbon atoms, -O-, It may be a group formed by combining at least one group selected from the group consisting of -S- and> N-R. This specific example is illustrated in the specific compound mentioned later.
- the bonding site between the linking group L1 and the partial structure of Formula (1) or Formula (2) is arbitrary. Specific binding sites are exemplified in the specific compounds described later.
- At least one hydrogen in the dimer compound of the present invention may be substituted with cyano, halogen or deuterium.
- R alkyl, aryl, cycloalkyl
- R aryl, heteroaryl, alkyl, cycloalkyl
- X 1 and X 2 are> N—R
- Halogen is fluorine, chlorine, bromine or iodine.
- the dimer compound which concerns on this 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 body compound is used.
- dimer compound of the present invention include, for example, compounds represented by the following chemical structural formulas.
- Me is a methyl group
- tBu is a tert-butyl group
- Ph is a phenyl group.
- the dimer compound of the present invention is a compound having two or more compounds after producing a polycyclic aromatic compound corresponding to the partial structure represented by the general formula (1) or (2).
- the polycyclic aromatic compound is bound by a linking group L1 by a known method, or two intermediates for forming the polycyclic aromatic compound are bound by a linking group L1 and bound by the linking group L1. It can be produced by subjecting two intermediate moieties to polycyclic aromatization.
- a polycyclic aromatic compound first combines A ring (a ring) with B ring (b ring) and C ring (c ring) by a linking group (a group containing X 1 and X 2 ) To prepare an intermediate (the first reaction), and then connect the A ring (a ring), the B ring (b ring) and the C ring (c ring) with a linking group (a group containing Y 1 ) The final product can be prepared (2nd reaction).
- first reaction for example, in the case of an etherification reaction, general reactions such as a nucleophilic substitution reaction and an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used.
- second reaction a tandem hetero Friedle-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used.
- the second reaction is a reaction to introduce Y 1 which bonds the A ring (a ring), the B ring (b ring) and the C ring (c ring) as shown in the following schemes (1) and (2).
- Y 1 is a boron atom and X 1 and X 2 are> NR is shown below.
- a hydrogen atom between X 1 and X 2 is ortho-metalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like.
- boron trichloride, boron tribromide and the like are added to transmetalate the lithium-boron, and then a Bronsted base such as N, N-diisopropylethylamine is added to make a tandem Bora Friedel-Crafts reaction. You can get things.
- a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.
- phosphorus trichloride (PCl 3 ) and sulfur (S 8 ) can be reacted to obtain a compound in which Y 1 is a phosphorus sulfide.
- m-CPBA m-chloroperbenzoic acid
- a compound in which Y 1 is Al, Ga, As, Si-R or Ge-R can be similarly produced by appropriately changing the raw materials.
- a known method can be used as a method of bonding the polycyclic aromatic compound corresponding to the partial structure represented by the general formula (1) or (2) produced as described above by the linking group L1 .
- known methods can be used as a method of bonding with a linking group L1 at the stage of an intermediate for forming a polycyclic aromatic compound.
- the dimer compound of the present invention also includes a compound in which at least a part of hydrogen atoms is substituted by cyano, halogen or deuterium, but such a compound is cyanated or halogenated at a desired site. It can manufacture similarly to the above by using the deuterated raw material.
- the dimer compound according to the present invention can be used as a material for an organic device.
- an organic device an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell etc. are mentioned, for example.
- FIG. 1 is a schematic cross-sectional view showing the organic EL element according to the present embodiment.
- the 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. Provided on the light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, and the electron transport layer 106 provided on the light emitting layer 105. And the cathode 108 provided on the electron injection layer 107.
- the organic electroluminescent device 100 is, 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 in reverse manufacturing order.
- An electron transport layer 106 provided on the light emitting layer 107, a light emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light emitting layer 105, and a hole transport layer 104;
- the hole injection layer 103 provided thereover and the anode 102 provided on the hole injection layer 103 may be provided.
- the minimum structural unit is configured of the anode 102, the light emitting layer 105 and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, the electron injection
- the layer 107 is an optional layer.
- Each of the layers may be a single layer or a plurality of layers.
- the layer which comprises an organic electroluminescent element other than the structure aspect of "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode” mentioned above, "Substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode", “substrate / Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode "," substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode "," substrate / Anode / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / light emitting
- the substrate 101 is a support of the organic electroluminescent device 100, and usually, quartz, glass, metal, plastic or the like is used.
- the substrate 101 is formed in a plate shape, a film shape, or a sheet shape according to the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used.
- a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate or polysulfone are preferable.
- soda lime glass, alkali-free glass, or the like may be used, and the thickness may be sufficient to maintain mechanical strength.
- the upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less.
- alkali-free glass is preferable because less elution ions from glass is preferable, but soda lime glass with a barrier coat such as SiO 2 may also be commercially available. it can.
- the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side in order to enhance the gas barrier properties, and a plate, a film or a sheet made of a synthetic resin having particularly low gas barrier properties is used as the substrate 101 When using it, it is preferable to provide a gas barrier film.
- the anode 102 plays a role of injecting holes into the light emitting layer 105.
- the hole injection layer 103 and / or the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 via these. .
- Materials forming the anode 102 include inorganic compounds and organic compounds.
- the inorganic compound for example, metal (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxide (oxide of indium, oxide of tin, indium-tin oxide (ITO), indium-zinc oxide Substances (IZO etc.), metal halides (copper iodide etc.), copper sulfide, carbon black, ITO glass, Nesa glass etc.
- the organic compound include polythiophenes such as poly (3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can select suitably from the substances 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 a current sufficient for light emission of the light emitting element can be supplied, and the resistance of the transparent electrode is not limited in view of the power consumption of the light emitting element.
- an ITO substrate of 300 ⁇ / sq or less functions as a device electrode, but at present it is also possible to supply a substrate of about 10 ⁇ / sq, for example 100 to 5 ⁇ / sq, 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 usually it is often used in the 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 into 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 via 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 or two or more hole injecting / transporting materials, or a mixture of a hole injecting / transporting material and a polymer binder. Be done.
- an inorganic salt such as iron (III) chloride may be added to the hole injecting / transporting material to form a layer.
- the hole injecting / transporting substance As the hole injecting / transporting substance, it is necessary to efficiently inject / transport holes from the positive electrode between the electrodes given an electric field, the hole injection efficiency is high, and the injected holes are efficiently transported. It is desirable to do.
- the substance has a small ionization potential, a large hole mobility, and a high stability, and is a substance which hardly generates an impurity serving as a trap during production and use.
- the dimer compound according to the present invention 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 charge transport materials for holes, p-type semiconductors, and known compounds used for hole injection layer and hole transport layer of organic electroluminescent device And any compound can be selected and used.
- carbazole derivatives N-phenylcarbazole, polyvinylcarbazole and the like
- biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole)
- triarylamine derivatives aromatic tertiary Polymer having amino in the main chain or side chain, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 , 4'-Diaminobiphenyl, N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl-N, N'-
- polycarbonates or styrene derivatives having the above-mentioned monomer in the side chain polyvinylcarbazole, polysilane etc. It is not particularly limited as long as it is a compound capable of forming a thin film necessary for manufacturing a device, injecting holes from the anode, and transporting holes.
- 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 donors.
- TCNQ tetracyanoquinone dimethane
- F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane
- the light emitting layer 105 is a layer that 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 (light emitting compound) that emits light by being excited by the recombination of holes and electrons, and can form a stable thin film shape, and a solid state Preferably, they are compounds that exhibit strong luminescence (fluorescence) efficiency.
- the dimer compound according to the present invention can be used as a material for the light emitting layer.
- the light emitting layer may be a single layer or a plurality of layers, and is formed of the material for the light emitting layer (host material, dopant material).
- the host material and the dopant material may be of one type or a combination of two or more.
- the dopant material may be contained in the entire host material, partially contained or may be contained. As a doping method, it can be formed by co-evaporation with a host material, but it may be simultaneously vapor-deposited after being previously mixed with the host material.
- the amount of host material used varies depending on the type of host material, and may be determined in accordance with the characteristics of the host material.
- the standard of the amount of 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 dimeric compounds according to the invention can also be used as host material.
- the amount of dopant material used varies depending on the type of dopant material, and may be determined in accordance with the characteristics of the dopant material.
- the standard for the amount of dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and still more preferably 0.1 to 10% by weight of the entire light emitting layer material. is there.
- the above range is preferable in that, for example, the concentration quenching phenomenon can be prevented.
- the dimeric compounds according to the invention can also be used as dopant materials.
- fused ring derivatives such as anthracene and pyrene, which have been known as light emitters
- bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives And tetraphenyl butadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives and the like.
- the dopant material that can be used in combination with the dimer compound according to the present invention is not particularly limited, and known compounds can be used, and it is selected from various materials according to the desired emission color. be able to.
- fused ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and chrysene
- benzoxazole derivatives benzothiazole derivatives, benzoimidazole derivatives, benzotriazole derivatives, oxazoles Derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenyl butadiene derivatives, cyclopentadiene derivatives, bis sty
- blue to blue-green dopant materials include, for example, naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perphenylene, fluorene, indene, chrysene and the like, and aromatic hydrocarbon compounds and derivatives thereof, furan, pyrrole, thiophene, Aromatic complexes such as silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene, etc.
- Aromatic complexes such as silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzo
- Ring compounds and derivatives thereof distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazole, thiazole, thiasia Azole derivatives such as carbazole, carbazole, oxazole, oxadiazole and triazole and metal complexes thereof and N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'-diphenyl-1, Aromatic amine derivatives represented by 1'-diamine may, for example, be mentioned.
- green to yellow dopant materials examples include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, naphthacene derivatives such as rubrene, etc.
- Preferred examples of the blue-green dopant material include compounds introduced with a substituent capable of achieving longer wavelength such as aryl, heteroaryl, arylvinyl, amino and cyano.
- naphthalimide derivatives such as bis (diisopropylphenyl) perylene tetracarboximide, perinone derivatives, rare earth complexes such as Eu complex having acetylacetone or benzoylacetone and phenanthroline as ligands, 4 -(Dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and analogs thereof, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridones Derivative, phenoxazine derivative, oxazine derivative, quinazoline derivative, pyrrolopyridine derivative, squarylium derivative, biolanthrone derivative, phenazine derivative, fenoxazo Derivatives, thiadiazolopyrene derivatives and
- a dopant it can be used suitably selected from the chemical compounds etc. which are described in Chemical Industry 2004 June issue page 13 and the reference etc. which were given to it.
- amines having a stilbene structure perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives or pyrene derivatives are particularly preferable.
- An amine having a stilbene structure is represented by, for example, the following formula.
- 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, but Ar 1 to Ar At least one of 3 has a stilbene structure, Ar 1 to Ar 3 may be substituted, and m is an integer of 1 to 4.
- the amine having a stilbene structure is more preferably diaminostilbene represented by the following formula.
- Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted.
- aryl having 6 to 30 carbon atoms are benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, stilbene, distyrylbenzene, distyrylbiphenyl, distyryl. And fluorene.
- amines having stilbene structure are 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) styryl]
- perylene derivatives include, for example, 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-2000-34234, JP-A-2001-267075, and JP-A-2001-217077 may be used.
- borane derivatives 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.
- borane derivatives described in WO 2000/40586 and the like may be used.
- the aromatic amine derivative is represented, for example, by the following formula.
- 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 It may be substituted
- n is an integer of 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 aryl having 6 to 30 carbon atoms
- n is 2 and aromatic amine derivatives are more preferred.
- aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, pentacene and the like.
- aromatic amine derivative as a chrysene type, for example, N, N, N ', N'-tetraphenyl chrysene-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'-di (p-
- N, N, N ', N'-tetraphenylpyrene-1,6-diamine N, N, N', N'-tetra (p-tolyl) pyrene-1,6 -Diamine
- N, N, N ', N'-tetra (m-tolyl) pyrene-1,6-diamine N, N, N', N'-tetrakis (4-isopropylphenyl) pyrene-1,6- Diamines
- anthracene type for example, N, N, N, N, N-tetraphenylanthracene-9,10-diamine, N, N, N ', N'-tetra (p-tolyl) anthracene-9,10-diamine N, N, N ', N'-tetra (m-tolyl) anthracene-9, 10-diamine, N, N, N ', N'- tetrakis (4-isopropylphenyl) anthracene-9, 10- diamine, N, N'-diphenyl-N, N'-di (p-tolyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-di (m-tolyl) anthracene-9,10- Diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) anthracene-9,10-diamine
- Examples of coumarin derivatives include coumarin-6, coumarin-334 and the like.
- coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, and JP-A-6-298758 may be used.
- Examples of pyran derivatives include the following DCM and DCJTB.
- the electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or into 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 via 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 an electron transport / injection material and a polymer binder.
- the electron injecting / transporting layer is a layer that injects electrons from the cathode and is responsible for transporting the electrons. It is desirable that the electron injection efficiency is high and the injected electrons are efficiently transported. For this purpose, it is preferable that the substance has a large electron affinity, a large electron mobility, and is excellent in stability and in which impurities serving as traps are less likely to be generated during production and use. However, considering the transport balance of holes and electrons, the electron transport capacity is so large when it mainly plays a role of being able to efficiently block the flow of holes from the anode to the cathode side without recombination.
- the electron injecting / transporting layer in the present embodiment may also include the function of a layer capable of efficiently blocking the movement of holes.
- the dimer compound according to the present invention can be used as a material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107.
- the photoconductive material can be optionally selected from compounds conventionally used conventionally as an electron transfer compound, and known compounds used in the electron injection layer and the electron transport layer of the organic electroluminescent device. .
- compounds comprising an aromatic ring or heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, pyrrole derivatives And at least one selected from a fused ring derivative thereof and a metal complex having an electron accepting nitrogen.
- fused 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, anthraquinone And quinone derivatives such as diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives.
- metal complexes having an electron accepting nitrogen include hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes. These materials may be used alone or in combination with different materials.
- pyridine derivatives naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazoles Derivatives (1,3-bis [(4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-) Triazole etc.), thiadiazole derivative, metal complex of oxine derivative, quinolinol metal complex, quinoxaline derivative, polymer of quinoxaline derivative, benzazole compound, gallium complex, pyrazole derivative, perfluorinated fluoride Nylene derivatives
- metal complexes having an electron accepting nitrogen can also be used, for example, hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, benzoquinoline metal complexes, etc. can give.
- hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, benzoquinoline metal complexes, etc. can give.
- quinolinol metal complexes quinolinol metal complexes, bipyridine derivatives, phenanthroline derivatives or borane derivatives are preferable.
- the quinolinol metal complex is a compound represented by the following general formula (E-1).
- R 1 to R 6 are hydrogen or a substituent
- M is Li, Al, Ga, Be or Zn
- n is an integer of 1 to 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-quinolinolate) 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-methylphenolate) aluminum, bis (2-methyl-8-) Quinolinolate) (4- Tylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis
- 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.
- carbon not used for binding of pyridine-pyridine or pyridine-G may be substituted.
- G in 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-dimesitylsilol, 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-dimesitylsilol, 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 hydrogen or a substituent, and adjacent groups may be bonded to each other to form a fused ring
- G represents a simple bond or an n-valent linking group
- n is 2 It is an integer of ⁇ 8.
- G in the general formula (E-3-2) for example, the same structural formula as G described in the section of bipyridine derivative can be mentioned.
- phenanthroline derivative examples 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-phenanthrolin-5-yl) pyridine, 1,3,5-tri (1,10-phenanthrolin-5-yl) benzene, 9,9'-difluoro And -bis (1,10-phenanthrolin-5-yl), vasocuproin and 1,3-bis (2-phenyl-1,10-phenanthrolin-9-yl) benzene.
- a phenanthroline derivative is used for the electron transporting layer and the electron injecting layer.
- the substituent itself has a three-dimensional steric structure, or with a phenanthroline skeleton or A derivative having a three-dimensional steric structure by steric repulsion with an adjacent substituent or a derivative in which a plurality of phenanthroline skeletons are linked is preferable.
- a compound including a conjugated bond, a substituted or unsubstituted aromatic hydrocarbon, or a substituted or unsubstituted aromatic heterocycle in a 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 hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, nitrogen-containing heterocycle which may be substituted, or cyano
- each of R 13 to R 16 independently represents optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl
- X is optionally substituted
- Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl
- n is each independently 0 It is an integer of ⁇ 3.
- each of R 11 and R 12 independently represents hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, nitrogen-containing heterocycle which may be substituted, or cyano
- each of R 13 to R 16 independently represents optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl
- R 21 and R 22 Each independently represents at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, optionally substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano
- X 1 Is an optionally substituted arylene having a carbon number of 20 or less
- n is each independently an integer of 0 to 3
- m is Independently an integer of 0 to 4.
- R 31 to R 34 each independently represent either methyl, isopropyl or phenyl
- R 35 and R 36 each independently represent any of hydrogen, methyl, isopropyl or phenyl It is.
- each of R 11 and R 12 independently represents hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, nitrogen-containing heterocycle which may be substituted, or cyano
- each of R 13 to R 16 independently represents optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl
- X 1 is a substituted And an arylene having 20 or less carbon atoms which may be substituted
- n is each independently an integer of 0 to 3.
- 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 hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, nitrogen-containing heterocycle which may be substituted, or cyano
- each of R 13 to R 16 independently represents optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl
- X 1 is a substituted arylene which may number 10 or less carbon atoms have been
- Y 1 is a substituted carbon atoms which may have 14 or less aryl
- n is an integer from 0 to 3 each independently.
- R 31 to R 34 each independently represent either methyl, isopropyl or phenyl
- R 35 and R 36 each independently represent any of 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. Particularly preferred is a benzimidazole derivative in which Ar 1 is anthryl which may be substituted.
- aryl having 6 to 30 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, acenaphthyl-1-yl, acenaphthyl-3-yl, acenaphthyl-4-yl, acenaphthyl-5-yl, and fluorene-1-l.
- benzimidazole derivatives are 1-phenyl-2- (4- (10-phenylanthracene-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- (naphthalene-2) -Yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -1-l Phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalen-2-yl) anthracene-9-yl) -1,2-diphenyl-1H-benzo [d] imidazole, 1- (4- (10) -(Naphthalen-2-yl) anthracene-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9- (9
- 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 materials can be used as long as the material has a certain reducibility, for example, alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, alkali From the group consisting of oxides of earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals At least one selected can be suitably used.
- alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), Ca (1.2. And alkaline earth metals such as 9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and materials having a work function of 2.9 eV or less are particularly preferable.
- more preferable reducing substances are alkali metals of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs.
- alkali metals are particularly high in reducing ability, and the addition of a relatively small amount to the material forming the electron transport layer or the electron injection layer can improve the emission luminance and prolong the life of the organic EL element.
- a combination of two or more alkali metals is also preferable as a reducing substance having a work function of 2.9 eV or less, and in particular, a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
- Cs By including Cs, the reduction ability can be efficiently exhibited, and by addition to the material for forming the electron transport layer or the electron injection layer, the emission luminance in the organic EL element can be improved and the lifetime can be prolonged.
- the cathode 108 plays a role of injecting electrons into the light emitting layer 105 via 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 can efficiently inject electrons into the organic layer, but the same material as the material 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 alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc. are preferable.
- Lithium, sodium, potassium, cesium, calcium, magnesium or alloys containing these low work function metals are effective for enhancing the electron injection efficiency to improve the device characteristics.
- metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals for electrode protection, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride It is preferable to stack a hydrocarbon-based polymer compound or the like as a preferred example.
- the method for producing these electrodes is also not particularly limited as long as conduction can be taken, such as resistance heating evaporation, electron beam evaporation, sputtering, ion plating and coating.
- ⁇ Binder which may be used in each layer>
- the materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer described above can form each layer independently, but polyvinyl chloride, polycarbonate, or the like as a polymer binder 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 Etc., and can be used by dispersing it in a solvent-soluble resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. is there.
- a solvent-soluble resin such as phenol resin, xylene
- Each layer constituting the organic electroluminescent element is formed of a material to be constituted of each layer by a method such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, spin coating or casting, or the like. It can be formed by using a thin film. There is no particular limitation on the film thickness of each layer formed in this way, and it can be appropriately set according to the property of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured by a crystal oscillation type film thickness measuring device or the like.
- the vapor deposition conditions differ depending on the type of material, the desired crystal structure and association structure of the film, and the like.
- the deposition conditions are generally: boat heating temperature +50 to + 400 ° C., vacuum degree 10 ⁇ 6 to 10 ⁇ 3 Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature ⁇ 150 to + 300 ° C., film thickness 2 nm to 5 ⁇ m It is preferable to set appropriately in the range.
- an organic electric field comprising a light emitting layer / electron transport layer / electron injection layer / cathode comprising anode / hole injection layer / hole transport layer / host material and dopant material
- a method for manufacturing a light emitting element is described. After forming a thin film of an anode material on a suitable substrate by vapor deposition or the like to prepare an anode, thin films of a hole injection layer and a hole transport layer are formed on the anode.
- a host material and a dopant material are co-deposited thereon to form a thin film to form a light emitting layer, an electron transporting layer and an electron injecting layer are formed on the light emitting layer, and a thin film made of a cathode material is deposited by evaporation or the like.
- the intended organic electroluminescent element is obtained by forming it as a cathode.
- the anode When a DC voltage is applied to the organic electroluminescent device thus obtained, the anode may be applied as + and the cathode may be applied as-polarity, and when a voltage of about 2 to 40 V is applied, it is transparent or semitransparent. Luminescence can be observed from the electrode side (anode or cathode, and both).
- the organic electroluminescent device also emits light when a pulse current or an alternating current is applied.
- the waveform of the alternating current to apply may be arbitrary.
- the present invention can also be applied to a display device provided with an organic electroluminescent device or a lighting device provided with an organic electroluminescent device.
- the display device or the illumination device provided with the organic electroluminescent device can be manufactured by a known method such as connecting the organic electroluminescent device according to the present embodiment and a known drive device, and can be DC drive, pulse drive, AC It can drive, using suitably well-known drive methods, such as a drive.
- Examples of the display device include a panel display such as a color flat panel display, a flexible display such as a flexible color organic electroluminescent (EL) display, and the like (for example, Japanese Patent Application Laid-Open Nos. 10-335066 and 2003-321546). See Japanese Patent Laid-Open Publication No. 2004-281086 etc.).
- a display method of a display a matrix and / or a segment system etc. are mentioned, for example.
- the matrix display and the segment display may coexist in the same panel.
- pixels for display are two-dimensionally arranged in a lattice shape, a mosaic shape, or the like, and a character or an image is displayed by a set of pixels.
- the shape and size of the pixels depend on the application. For example, for displaying images and characters on personal computers, monitors, and televisions, square pixels with one side of 300 ⁇ m or less are usually used, and in the case of a large display such as a display panel, pixels with one side of mm order become.
- monochrome display pixels of the same color may be arranged, but in color display, red, green and blue pixels are displayed side by side. In this case, there are typically delta types and stripe types.
- a line sequential driving method or an active matrix may be used.
- the line-sequential drive has an advantage of a simpler structure
- the active matrix may be superior in some cases in consideration of the operation characteristics, and therefore, it is necessary to properly use this depending on the application.
- a pattern is formed so as to display predetermined information, and a predetermined area is made to emit light.
- predetermined information For example, time and temperature displays on digital watches and thermometers, operation status displays on audio devices and induction cookers, and panel displays on automobiles can be mentioned.
- the lighting device examples include a lighting device such as interior lighting, a backlight of a liquid crystal display device, and the like (for example, JP 2003-257621 A, JP 2003-277741 A, and JP 2004-119211 A). Etc.).
- Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light themselves, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, and the like.
- backlights for liquid crystal display devices particularly for personal computer applications where thinning is an issue, considering that thinning is difficult because the conventional method is composed of a fluorescent lamp and a light guide plate
- the backlight using the light emitting element according to is characterized by being thin and lightweight.
- the dimer compound according to the present invention can be used for producing an organic field effect transistor, an organic thin film solar cell, etc. in addition to the organic electroluminescent device described above.
- An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and a gate electrode is provided 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 flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current.
- a field effect transistor is easier to miniaturize than a simple transistor (bipolar transistor), and is often used as an element constituting an integrated circuit or the like.
- a source electrode and a drain electrode are provided in contact with the organic semiconductor active layer formed using the dimer compound according to the present invention, and further, the organic semiconductor active layer is in contact
- the gate electrode may be provided with the insulating layer (dielectric layer) interposed therebetween.
- Examples of the element structure include the following structures.
- the organic field effect transistor configured in this way is The present invention can be applied as a pixel drive switching element of an active matrix drive type liquid crystal display or an organic electroluminescence display.
- the organic thin film solar cell has 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 stacked 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 dimer compound according to the present invention can be used as a material of the hole transport layer, the p-type semiconductor layer, the n-type semiconductor layer, and the electron transport layer according to the physical properties.
- the dimer 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 be appropriately provided with a hole block layer, an electron block layer, an electron injection layer, a hole injection layer, a smoothing layer and the like in addition to the above.
- known materials used for the organic thin film solar cell can be appropriately selected and used in combination.
- the reaction solution was cooled to room temperature, filtered through silica gel (eluent: toluene), and the solvent was evaporated under reduced pressure to give a crude product.
- the crude product obtained by using an ultrasonic crusher is washed with methanol, and the desired product 5,5- (1,3-phenylenebis (sulfandiyl)) bis (N 1 , N 1 , N 3) , N 3 -tetraphenylbenzene-1,3-diamine) (7.46 g, 86% yield) was obtained as a white solid.
- the filtrate was washed three times with water and dried over anhydrous sodium sulfate.
- the solution obtained is concentrated to obtain a composition organism, and the composition organism obtained is purified by silica gel chromatography (toluene) and then concentrated to give 1,3-bis (3,5-dichlorophenoxy). Benzene (15.5 g, 37% yield) was obtained as a colorless liquid.
- the reaction solution was cooled to room temperature, filtered through silica gel (eluent: toluene), and the solvent was evaporated under reduced pressure to give a crude product.
- reaction solution was distilled off under reduced pressure to obtain a crude product.
- the obtained crude product is filtered using Florisil (eluent: toluene), and the solvent of the filtrate is distilled off, and then it is washed with acetonitrile using an ultrasonic grinder, and the compound (1-5400) is a yellow solid Got as.
- the other dimer compound of the present invention can be synthesized by a method according to the above-described synthesis example, by appropriately changing the starting compound. Next, evaluation of basic physical properties of the dimer compound and a preparation example of the organic EL element will be described.
- Evaluation method of basic physical properties As a method of evaluating the absorption characteristics and the light emission characteristics (fluorescence and phosphorescence) of a compound, the compound may be dissolved in a solvent and evaluated in a solvent or in a thin film state. Furthermore, when evaluating in the thin film state, depending on the usage mode of the compound to be evaluated in the organic EL element, the compound to be evaluated is dispersed in an appropriate matrix material in the case of thin filming only the compound to be evaluated. And may be evaluated for thin film formation.
- PMMA polymethyl methacrylate
- a thin film sample dispersed in PMMA is prepared, for example, by dissolving PMMA and a compound to be evaluated in toluene, and then forming a thin film on a transparent support substrate (10 mm ⁇ 10 mm) made of quartz by a spin coating method. Can.
- a transparent support substrate (10 mm x 10 mm x 1.0 mm) made of quartz is fixed to a substrate holder of a commercial deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), a molybdenum deposition boat containing a host material, and a dopant material Mount the molybdenum evaporation boat.
- the vacuum chamber is depressurized to 5 ⁇ 10 -4 Pa, and the deposition boat containing the host material and the deposition boat containing the dopant material are simultaneously heated to obtain an appropriate film thickness.
- Form a mixed film of material and dopant material is controlled in accordance with the set weight ratio of the host material and the dopant material.
- photoluminescence was measured at room temperature by excitation at an appropriate excitation wavelength.
- the sample was measured in a state of being immersed in liquid nitrogen (temperature 77 K) using an attached cooling unit.
- the delay time from the excitation light irradiation to the measurement start was adjusted using an optical chopper. The sample was excited at an appropriate excitation wavelength to measure photoluminescence.
- the fluorescence quantum yield is measured using an absolute PL quantum yield measurement apparatus (C9920-02G, manufactured by Hamamatsu Photonics Co., Ltd.).
- the fluorescence lifetime is measured at 300 K using a fluorescence lifetime measuring apparatus (C11367-01, manufactured by Hamamatsu Photonics Co., Ltd.). Observe the fast and slow components of the fluorescence lifetime at the maximum emission wavelength measured at the appropriate excitation wavelength.
- fluorescence lifetime measurement at room temperature of a general organic EL material that emits fluorescence due to the deactivation of the triplet component by heat, a slow component involving the triplet component derived from phosphorescence is hardly observed .
- a slow component is observed in the compound to be evaluated, it indicates that triplet energy having a long excitation life is transferred to singlet energy by thermal activation and observed as delayed fluorescence.
- ⁇ EST is, for example, “Purely organic electroluminescent material 100% conversion from electricity to light”, H. Kaji, H. Suzuki, T. Fukushima, K. Shizu, K. Katsuaki, S. Kubo, T. Komino, It can also be calculated by the method described in H. Oiwa, F. Suzuki, A. Wakamiya, Y. Murata, C. Adachi, Nat. Commun. 2015, 6, 8476.
- the phosphorescence spectrum was measured by preparing a thin film-formed substrate (made of quartz) in which the compound (1-201) was dispersed in PMMA at a concentration of 1% by weight, and excited at an excitation wavelength of 340 nm to measure photoluminescence. As a result, the maximum emission wavelength was 492 nm, E T was calculated to 2.52 eV.
- a thin film-formed substrate made of quartz
- E T was calculated to 2.52 eV.
- the compound (1-201) since the compound (1-201) has a deep blue fluorescence spectrum, high fluorescence quantum yield and appropriate energy (Es, E T ), it can be particularly expected to be applied to a light emitting layer .
- the evaluation items of the organic EL element include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum emission spectrum There are wavelength (nm) and half width (nm). As these evaluation items, values at appropriate light emission luminance can be used.
- the quantum efficiency of the organic EL element includes internal quantum efficiency and external quantum efficiency.
- the internal quantum efficiency is the ratio of external energy injected as electrons (or holes) into the light emitting layer to be converted into photons purely Is shown.
- the external quantum efficiency is calculated based on the amount of this photon emitted to the outside of the device, and some of the photons generated in the light emitting layer are continuously absorbed or reflected inside the device. Therefore, the external quantum efficiency is lower than the internal quantum efficiency because it is not emitted outside the device.
- the method of measuring the spectral radiance (emission spectrum) and the external quantum efficiency is as follows.
- the device is made to emit light by applying a voltage using a voltage / current generator R6144 manufactured by Advantest.
- the spectral radiance in the visible light region is measured from the direction perpendicular to the light emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON. Assuming that the light emitting surface is a complete diffusion surface, the number of photons at each wavelength is a value obtained by dividing the measured value of the spectral radiance of each wavelength component by the wavelength energy and multiplying by ⁇ .
- the number of photons is integrated over the entire wavelength region observed, and this is taken as the total number of photons emitted from the device.
- the external quantum efficiency is the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device, where the number of carriers injected into the device is the value obtained by dividing the applied current value by the elementary charge.
- the half width of the emission spectrum is determined as the width between the upper and lower wavelengths at which the intensity is 50% around the maximum emission wavelength.
- Examples of the layer configuration of the organic EL element include the layer configurations of Table 1.
- the application of the dimer compound of the present invention is not limited to the following layer constitution, and the film thickness and constituent materials of each layer can be appropriately changed according to the basic physical properties of the dimer compound of the present invention.
- HI-1 hole injection layer material
- HAT-CN hole injection layer material
- HT-1 hole transport layer material
- HT-2 hole transport layer material
- the organic EL element having the layer configuration of Table 1 can be manufactured by the following procedure. First, a 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate (manufactured by Atsugi Micro Co., Ltd.) having an ITO film formed to a thickness of 150 nm by sputtering is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (made by Choshu Sangyo Co., Ltd.), and HI-1 (hole injection layer material), HAT-CN (hole injection layer material), HT-1 (hole material).
- the following layers are sequentially formed on the ITO film of the transparent support substrate.
- the vacuum chamber is depressurized to 1 ⁇ 10 -4 Pa, and HI-1 is heated to deposit 40 nm thick, and HAT-CN is heated to 5 nm thick.
- a hole injection layer consisting of two layers is formed.
- HT-1 is heated to deposit to a film thickness of 15 nm, and HT-2 is further heated to deposit a film to a thickness of 10 nm to form a two-layer hole transport layer.
- EMH 1 and the compound (1-201) are simultaneously heated and vapor deposited to a film thickness of 25 nm to form a light emitting layer.
- the deposition rate is adjusted so that the weight ratio of EMH1 to compound (1-201) is approximately 98: 2.
- ET-1 is heated to deposit to a film thickness of 5 nm
- ET-2 and Liq are simultaneously heated to deposit to a film thickness of 25 nm to form an electron transport layer consisting of two layers.
- Do. The deposition rate is adjusted so that the weight ratio of ET-2 to Liq is approximately 50 to 50.
- the deposition rate of each layer is 0.01 to 1 nm / second.
- Liq is heated to deposit 1 nm thick at a deposition rate of 0.01 to 0.1 nm / sec, and then magnesium and silver are simultaneously heated to deposit 100 nm thick.
- Form a cathode The deposition rate is adjusted between 0.1 nm to 10 nm / sec so that the atomic ratio of magnesium to silver is 10: 1.
- an organic EL element is obtained.
- luminance, chromaticity, external quantum efficiency and the like can be measured by applying a DC voltage with the ITO electrode as an anode and the MgAg electrode as a cathode.
- the dimer compound of the present invention can be evaluated as an organic EL element by evaluating its basic physical properties in the same manner as the compound (1-201) and the compound (1-5400). However, it can also be used as a material for other layers such as a material for charge transport layer other than the host material according to the basic physical properties.
- an excellent polycyclic aromatic dimer compound which can be used for example, as a material for an organic EL element
- this dimer compound it is possible to provide an excellent organic EL element, a display device provided with the same, a lighting device provided with the same, and the like.
- organic electroluminescent device 101 substrate 102 anode 103 hole injection layer 104 hole transport layer 105 light emitting layer 106 electron transport layer 107 electron injection layer 108 cathode
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Abstract
Description
2つの下記一般式(1)で表される部分構造と、当該2つの部分構造を連結する連結基L1とからなる二量体化合物であって、
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリール、アルキルまたはシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-R、>Sまたは>Seであり、前記>N-RのRは置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいアルキルまたは置換されていてもよいシクロアルキルであり、前記>N-RのRは連結基L2により前記A環、B環および/またはC環と結合していてもよい。)
式(1)で表される部分構造は、2つが同じ構造であっても異なった構造であってもよく、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~30のアリーレン、炭素数2~30のヘテロアリーレン、炭素数1~24のアルキレン、炭素数1~24のアルケニレン、炭素数1~24のアルキニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、前記>N-RのRは炭素数6~16のアリール、炭素数2~20のヘテロアリール、炭素数1~12のアルキルまたは炭素数3~16のシクロアルキルであり、連結基L1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2~20のヘテロアリール炭素数1~12のアルキルまたは炭素数3~16のシクロアルキルで置換されていてもよく、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい、二量体化合物。
A dimer compound comprising two partial structures represented by the following general formula (1) and a linking group L1 linking the two partial structures,
Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
Y 1 is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R in Si-R and Ge-R is aryl, alkyl or cycloalkyl; Yes,
X 1 and X 2 are each independently>O,>NR,> S or> Se, and R in> NR is optionally substituted aryl, which may be substituted Heteroaryl, alkyl which may be substituted, or cycloalkyl which may be substituted, wherein R in> N—R is connected to the A ring, B ring and / or C ring via a linking group L 2, It is also good. )
The partial structure represented by formula (1) may have the same structure or different structures from each other, provided that in the two partial structures, Y 1 is both B and X 1 and X 2 are both> The case of O is excluded, and the case where Y 1 is both P 共 に O, X 1 and X 2 are both> O is also excluded.
The linking
The dimer compound in which at least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
上記式(1)中、
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換または無置換のアリール、置換または無置換のヘテロアリール、置換または無置換のジアリールアミノ、置換または無置換のジヘテロアリールアミノ、置換または無置換のアリールヘテロアリールアミノ、置換または無置換のアルキル、置換または無置換のシクロアルキル、置換または無置換のアルコキシまたは置換または無置換のアリールオキシで置換されていてもよく、また、これらの環はY1、X1およびX2から構成される上記式中央の縮合2環構造と結合を共有する5員環または6員環を有し、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリール、アルキルまたはシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-R、>Sまたは>Seであり、前記>N-RのRはアルキルまたはシクロアルキルで置換されていてもよいアリール、アルキルまたはシクロアルキルで置換されていてもよいヘテロアリール、アルキルまたはシクロアルキルであり、前記>N-RのRは-O-、-S-、-C(-R)2-および単結合から選択される連結基L2により前記A環、B環および/またはC環と結合していてもよく、前記-C(-R)2-のRは、水素、アルキルまたはシクロアルキルであり、そして、
式(1)で表される部分構造は、2つが同じ構造であっても異なった構造であってもよく、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~16のアリーレン、炭素数2~20のヘテロアリーレン、炭素数1~12のアルキレン、炭素数1~12のアルケニレン、炭素数1~12のアルキニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、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、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、連結基L1における少なくとも1つの水素は炭素数6~12のアリール、炭素数2~15のヘテロアリール、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルで置換されていてもよく、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい、
項1に記載する二量体化合物。 Item 2.
In the above formula (1),
Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted The ring may be substituted with unsubstituted aryloxy, and these rings may be 5- or 6-membered rings sharing a bond with the fused two-ring structure at the center of the above formula composed of Y 1 , X 1 and X 2 Have a ring,
Y 1 is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R in Si-R and Ge-R is aryl, alkyl or cycloalkyl; Yes,
X 1 and X 2 are each independently>O,>N—R,> S or> Se, wherein R in> N—R is aryl optionally substituted with alkyl or cycloalkyl Or heteroaryl, alkyl or cycloalkyl optionally substituted with cycloalkyl, wherein R in> N—R is selected from —O—, —S—, —C (—R) 2 — and a single bond A linking group L2 may bind to the ring A, ring B and / or ring C, R in -C (-R) 2- is hydrogen, alkyl or cycloalkyl, and
The partial structure represented by formula (1) may have the same structure or different structures from each other, provided that in the two partial structures, Y 1 is both B and X 1 and X 2 are both> The case of O is excluded, and the case where Y 1 is both P 共 に O, X 1 and X 2 are both> O is also excluded.
The linking
At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
上記部分構造が下記一般式(2)で表される、項1に記載する二量体化合物。
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11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、シクロアルキル、アルコキシ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、アルキルまたはシクロアルキルで置換されていてもよく、また、R1~R11のうちの隣接する基同士は結合してa環、b環またはc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、シクロアルキル、アルコキシ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、アルキルまたはシクロアルキルで置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRは炭素数6~12のアリール、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-R、>Sまたは>Se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、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、前記>N-RのRは-O-、-S-、-C(-R)2-および単結合から選択される連結基L2により前記a環、b環および/またはc環と結合していてもよく、前記-C(-R)2-のRは炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、そして、
式(2)で表される部分構造は、2つが同じ構造であっても異なった構造であってもよく、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~12のアリーレン、炭素数2~15のヘテロアリーレン、炭素数1~6のアルキレン、炭素数1~6のアルケニレン、炭素数1~6のアルキニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、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、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。 Item 3.
Item 2. The dimer compound described in
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylamino Heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and R 1 to Adjacent groups of R 11 may combine to form an aryl ring or heteroaryl ring with the a ring, b ring or c ring, and at least one hydrogen in the formed ring is aryl, heteroaryl , Diarylamino, diheteroarylamino, arylheteroarylamino, aru Le, cycloalkyl, may be substituted by alkoxy or aryloxy, at least one hydrogen in these aryl, heteroaryl, it may be substituted by alkyl or cycloalkyl,
Y 1 is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R in the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms , Alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons,
X 1 and X 2 are each independently>O,>NR,> S or> Se, wherein R in> NR is an aryl having 6 to 12 carbon atoms, and 2 to 15 carbon atoms Heteroaryl, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, wherein R in> N—R is selected from —O—, —S—, —C (—R) 2 — and a single bond The linking group L2 may be linked to the a ring, b ring and / or c ring, and R in -C (-R) 2- is alkyl having 1 to 6 carbons or 3 to 6 carbons 14 cycloalkyl and
The partial structure represented by Formula (2) may have the same structure or different structures from each other, provided that in the two partial structures, Y 1 is both B and X 1 and X 2 are both> The case of O is excluded, and the case where Y 1 is both P 共 に O, X 1 and X 2 are both> O is also excluded.
The linking
At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
上記式(2)中、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11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、ジアリールアミノ(ただしアリールは炭素数6~12のアリール)、炭素数1~20のアルキルまたは炭素数3~20のシクロアルキルであり、また、R1~R11のうちの隣接する基同士は結合してa環、b環またはc環と共に炭素数9~16のアリール環または炭素数6~15の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つの水素は炭素数6~10のアリール、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルで置換されていてもよく、
Y1は、B、P、P=O、P=SまたはSi-Rであり、前記Si-RのRは炭素数6~10のアリール、炭素数1~4のアルキルまたは炭素数5~10のシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-Rまたは>Sであり、前記>N-RのRは炭素数6~10のアリール、炭素数1~4のアルキルまたは炭素数5~10のシクロアルキルであり、そして、
式(2)で表される部分構造は、2つが同じ構造であり、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~12のアリーレン、炭素数1~6のアルキレン、炭素数1~6のアルケニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、前記>N-RのRは炭素数6~10のアリールであり、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい、
項3に記載する二量体化合物。 Item 4.
In the above formula (2),
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently hydrogen, aryl having 6 to 30 carbon atoms, carbon A heteroaryl of 2 to 30 and diarylamino (wherein aryl is aryl of 6 to 12 carbons), alkyl of 1 to 20 carbons or cycloalkyl of 3 to 20 carbons, and R 1 to R 11 And the adjacent groups may combine to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring or c ring; At least one hydrogen may be substituted with aryl having 6 to 10 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons,
Y 1 is B, P, P = O, P = S or Si—R, and R in the above Si—R is aryl having 6 to 10 carbons, alkyl having 1 to 4 carbons, or 5 to 10 carbons Cycloalkyl, and
X 1 and X 2 are each independently>O,> N—R or> S, and R in> N—R is aryl having 6 to 10 carbons, alkyl having 1 to 4 carbons or carbon Several 5-10 cycloalkyls, and
In the partial structure represented by the formula (2), two are the same structure, provided that in the two partial structures Y 1 is both B and X 1 and X 2 are both> O, and Y is Also when 1 is both P = O, X 1 and X 2 are both> O,
The linking
At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
Item 3. A dimer compound described in item 3.
下記いずれかの化学構造式で表される、項1に記載する二量体化合物。
項1ないし5のいずれかに記載する二量体化合物を含有する、有機デバイス用材料。 Item 6.
A material for an organic device, comprising the dimer compound according to any one of
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、項6に記載する有機デバイス用材料。 Item 7.
7. The organic device material according to item 6, wherein the organic device material is an organic electroluminescent device material, an organic field effect transistor material, or an organic thin film solar cell material.
発光層用材料である、項7に記載する有機電界発光素子用材料。
8. A material for an organic electroluminescent device according to item 7, which is a material for a light emitting layer.
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、項8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。 Item 9.
Item 9. An organic electroluminescent device comprising: a pair of electrodes consisting of an anode and a cathode; and a light emitting layer disposed between the pair of electrodes and containing the material for a light emitting layer described in
前記陰極と前記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、項9に記載する有機電界発光素子。 Item 10.
It has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer comprises a quinolinol metal complex, a pyridine derivative, a phenanthroline derivative Item 10. The organic electroluminescent device according to item 9, containing at least one selected from the group consisting of borane derivatives and benzimidazole derivatives.
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、項10に記載の有機電界発光素子。 Item 11.
The electron transport layer and / or the electron injection layer may further be selected from alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, and alkaline earth metals. Item 10, containing at least one selected from the group consisting of halides, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals The organic electroluminescent element as described in.
項9~11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または照明装置。 Item 12.
Item 12. A display device or lighting device comprising the organic electroluminescent device according to any one of items 9 to 11.
本発明は、2つの下記一般式(1)で表される部分構造と、当該2つの部分構造を連結する連結基L1とからなる二量体化合物である。本発明は、好ましくは、2つの下記一般式(2)で表される部分構造と、当該2つの部分構造を連結する連結基L1とからなる二量体化合物である。なお、以降の説明で用いる全ての構造式中の各符号の定義は上述した定義と同じである。
この規定は、下記式(2-3-1)で表される、X1やX2が縮合環B’および縮合環C’に取り込まれた環構造を有する部分構造で表現できる。すなわち、例えば一般式(2)におけるb環(またはc環)であるベンゼン環に対してX1(またはX2)を取り込むようにして他の環が縮合して形成されるB’環(またはC’環)を有する化合物である。形成されてできた縮合環B’(または縮合環C’)は例えばフェノキサジン環、フェノチアジン環またはアクリジン環である。
また、上記規定は、下記式(2-3-2)や式(2-3-3)で表される、X1および/またはX2が縮合環A’に取り込まれた環構造を有する部分構造でも表現できる。すなわち、例えば一般式(2)におけるa環であるベンゼン環に対してX1(および/またはX2)を取り込むようにして他の環が縮合して形成されるA’環を有する部分構造である。形成されてできた縮合環A’は例えばフェノキサジン環、フェノチアジン環またはアクリジン環である。 Here, the definition of “in R of> N—R is bonded to the ring A, ring B and / or ring C via a linking group L2” in the general formula (1) is “in the general formula (2) R in> NR is connected to the a ring, b ring and / or c ring via a linking group L2 selected from —O—, —S—, —C (—R) 2 — and a single bond Correspond to the provision of
This definition can be expressed by a partial structure represented by the following formula (2-3-1), which has a ring structure in which X 1 or X 2 is incorporated into fused ring B ′ and fused ring C ′. That is, for example, the B ′ ring (or the ring formed by condensation of other rings such that X 1 (or X 2 ) is incorporated into the benzene ring which is ring b (or ring c) in the general formula (2) A compound having a C 'ring). The fused ring B '(or fused ring C') formed and formed is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
Further, the above definition is a moiety represented by the following formula (2-3-2) or (2-3-3) and having a ring structure in which X 1 and / or X 2 is incorporated into the fused ring A ′ It can also be expressed by structure. That is, for example, it is a partial structure having an A ′ ring formed by condensing other rings with X 1 (and / or X 2 ) being incorporated into a benzene ring which is a ring in the general formula (2) is there. The fused ring A 'formed and formed is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
本発明の二量体化合物は、一般式(1)や(2)で表される部分構造に相当する多環芳香族化合物を製造した後に2つの多環芳香族化合物を公知の方法により連結基L1で結合するか、多環芳香族化合物を形成するための中間体を2つ、連結基L1で結合しておき、この連結基L1で結合した2つの中間体部分を多環芳香族化することで製造することができる。 2. Method for Producing Polycyclic Aromatic-Based Dimer Compound The dimer compound of the present invention is a compound having two or more compounds after producing a polycyclic aromatic compound corresponding to the partial structure represented by the general formula (1) or (2). The polycyclic aromatic compound is bound by a linking group L1 by a known method, or two intermediates for forming the polycyclic aromatic compound are bound by a linking group L1 and bound by the linking group L1. It can be produced by subjecting two intermediate moieties to polycyclic aromatization.
本発明に係る二量体化合物は、有機デバイス用材料として用いることができる。有機デバイスとしては、例えば、有機電界発光素子、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が挙げられる。 3. Organic Device The dimer compound according to the present invention can be used as a material for an organic device. As an organic device, an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell etc. are mentioned, for example.
本発明に係る二量体化合物は、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。 3-1. Organic Electroluminescent Device The dimer compound according to the present invention can be used, for example, as a material of an organic electroluminescent device. Below, the organic EL element which concerns on this embodiment is demonstrated in detail based on drawing. FIG. 1 is a schematic cross-sectional view showing the organic EL element according to the present embodiment.
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。 <Structure of Organic Electroluminescent Device>
The
基板101は、有機電界発光素子100の支持体であり、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。 <Substrate in Organic Electroluminescent Device>
The
陽極102は、発光層105へ正孔を注入する役割を果たす。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。 <Anode in Organic Electroluminescent Device>
The
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。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。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。 <Hole Injection Layer in Organic Electroluminescent Device, Hole Transport Layer>
The
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層である。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、本発明に係る二量体化合物を用いることができる。 <Light emitting layer in organic electroluminescent device>
The
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。 Specific examples of amines having stilbene structure are 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) styryl] -benzene, 2,7-bis [4'-bis (diphenylamino) styryl] -9,9-dimethyl Fluorene, 4,4'-bis (9-ethyl-3-cal) And bazovinylene) -biphenyl, 4,4'-bis (9-phenyl-3-carbazovinylene) -biphenyl and the like.
Further, amines having a stilbene structure described in JP-A-2003-349056, JP-A-2001-307884, etc. may be used.
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。 Examples of perylene derivatives include, for example, 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.
Further, 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-2000-34234, JP-A-2001-267075, and JP-A-2001-217077 may be used.
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。 Examples of borane derivatives 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.
In addition, borane derivatives described in WO 2000/40586 and the like may be used.
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。 In addition to the above, [4- (4-diphenylamino-phenyl) naphthalen-1-yl] -diphenylamine, [6- (4-diphenylamino-phenyl) naphthalen-2-yl] -diphenylamine, 4,4 ′ -Bis [4-diphenylaminonaphthalen-1-yl] biphenyl, 4,4'-bis [6-diphenylaminonaphthalen-2-yl] biphenyl, 4,4 "-bis [4-diphenylaminonaphthalen-1-yl] ] -P-terphenyl, 4,4 "-bis [6-diphenylaminonaphthalen-2-yl] -p-terphenyl and the like.
In addition, aromatic amine derivatives described in JP-A-2006-156888 may be used.
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。 Examples of coumarin derivatives include coumarin-6, coumarin-334 and the like.
In addition, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, and JP-A-6-298758 may be used.
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。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。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。 <Electron Injection Layer in Organic Electroluminescent Device, Electron Transport Layer>
The
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。 <Cathode in Organic Electroluminescent Device>
The cathode 108 plays a role of injecting electrons into the
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。 <Binder which may be used in each layer>
The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer described above can form each layer independently, but polyvinyl chloride, polycarbonate, or the like as a polymer binder 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 Etc., and can be used by dispersing it in a solvent-soluble resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. is there.
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、ボート加熱温度+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。 <Method of Manufacturing Organic Electroluminescent Device>
Each layer constituting the organic electroluminescent element is formed of a material to be constituted of each layer by a method such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, spin coating or casting, or the like. It can be formed by using a thin film. There is no particular limitation on the film thickness of each layer formed in this way, and it can be appropriately set according to the property of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured by a crystal oscillation type film thickness measuring device or the like. In the case of thin film formation using a vapor deposition method, the vapor deposition conditions differ depending on the type of material, the desired crystal structure and association structure of the film, and the like. The deposition conditions are generally: boat heating temperature +50 to + 400 ° C., vacuum degree 10 −6 to 10 −3 Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature −150 to + 300 ° C., film thickness 2 nm to 5 μm It is preferable to set appropriately in the range.
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。 <Application Example of Organic Electroluminescent Device>
The present invention can also be applied to a display device provided with an organic electroluminescent device or a lighting device provided with an organic electroluminescent device. The display device or the illumination device provided with the organic electroluminescent device can be manufactured by a known method such as connecting the organic electroluminescent device according to the present embodiment and a known drive device, and can be DC drive, pulse drive, AC It can drive, using suitably well-known drive methods, such as a drive.
本発明に係る二量体化合物は、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。 3-2. Other Organic Devices The dimer compound according to the present invention can be used for producing an organic field effect transistor, an organic thin film solar cell, etc. in addition to the organic electroluminescent device described above.
(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。 In the structure of the organic field effect transistor, generally, a source electrode and a drain electrode are provided in contact with the organic semiconductor active layer formed using the dimer compound according to the present invention, and further, the organic semiconductor active layer is in contact The gate electrode may be provided with the insulating layer (dielectric layer) interposed therebetween. Examples of the element structure include the following structures.
(1) 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 The organic field effect transistor configured in this way is The present invention can be applied as a pixel drive switching element of an active matrix drive type liquid crystal display or an organic electroluminescence display.
化合物(1-201):1,3-ビス(5,9-ジフェニル-5,9-ジヒドロ-5,9-ジアザ-13bボラナフト[3,2,1-de]アントラセン-7-イル)チオ)ベンゼンの合成
Compound (1-201): 1,3-bis (5,9-diphenyl-5,9-dihydro-5,9-diaza-13b boranaphtho [3,2,1-de] anthracene-7-yl) thio) Synthesis of benzene
窒素雰囲気下、1,3-ジヨードベンゼン(4.48g、14mmol)、3,5-ジブロモベンゼンチオール(5.50g、31mmol)、炭酸カリウム(4.27g、31mmol)をN,N-ジメチルホルムアミド(DMF)150mLへ溶解させ、そこへヨウ化銅(0.286g、1.5mmol)加え、100℃で4時間撹拌した後、反応液を冷却し、減圧下溶媒を留去し粗生成物を得た。シリカゲルを用いて得られた粗生成物を濾過し(溶離液:ヘキサン)、その後、超音波粉砕機を用いて残渣物をヘキサンで洗浄し、目的物である1,3-ビス((3,5-ジクロロフェニル)チオ)ベンゼン(4.73g、収率81%)を白色固体として得た。
In a nitrogen atmosphere, 1,3-diiodobenzene (4.48 g, 14 mmol), 3,5-dibromobenzenethiol (5.50 g, 31 mmol), potassium carbonate (4.27 g, 31 mmol) with N, N-dimethylformamide After dissolving in 150 mL of (DMF) and adding copper iodide (0.286 g, 1.5 mmol) thereto and stirring at 100 ° C. for 4 hours, the reaction solution is cooled and the solvent is distilled off under reduced pressure to give a crude product Obtained. The crude product obtained using silica gel is filtered (eluent: hexane), and then the residue is washed with hexane using an ultrasonic crusher to obtain the
1H-NMR(400MHz,CDCl3):δ=7.11(d,4H)、7.21(t,2H)、7.34-7.37(m,3H)、7.39(s,2H). The structure of the compound obtained was confirmed by NMR spectrum.
1 H-NMR (400 MHz, CDCl 3 ): δ = 7.11 (d, 4 H), 7.21 (t, 2 H), 7.34-7. 37 (m, 3 H), 7.39 (s, 7 (s, 7) 2H).
窒素雰囲気下、1,3-ビス((3,5-ジクロロフェニル)チオ)ベンゼン(3.56g、8.1mmol)、ジフェニルアミン(7.66g、45mmol)、Pd2(dba)3(0.456mg、0.50mmol)、トリtertブチルホスフィン(0.215g、1.1mmol)、NaOtBu(6.77g、70mmol)をトルエン(300ml)に溶解させ、110℃で18時間加熱撹拌した。反応液を室温まで冷却し、シリカゲルを用いて濾過し(溶離液:トルエン)、溶媒を減圧留去して粗生成物を得た。超音波粉砕機を用いて得られた粗生成物をメタノールで洗浄し、目的物である5,5-(1,3-フェニレンビス(サルファンジイル))ビス(N1,N1,N3,N3-テトラフェニルベンゼン-1,3-ジアミン)(7.46g、収率86%)を白色固体として得た。
In a nitrogen atmosphere, 1,3-bis ((3,5-dichlorophenyl) thio) benzene (3.56 g, 8.1 mmol), diphenylamine (7.66 g, 45 mmol), Pd 2 (dba) 3 (0.456 mg, 0.50 mmol), tritertbutyl phosphine (0.215 g, 1.1 mmol), NaOtBu (6.77 g, 70 mmol) were dissolved in toluene (300 ml), and the mixture was heated and stirred at 110 ° C. for 18 hours. The reaction solution was cooled to room temperature, filtered through silica gel (eluent: toluene), and the solvent was evaporated under reduced pressure to give a crude product. The crude product obtained by using an ultrasonic crusher is washed with methanol, and the desired product 5,5- (1,3-phenylenebis (sulfandiyl)) bis (N 1 , N 1 , N 3) , N 3 -tetraphenylbenzene-1,3-diamine) (7.46 g, 86% yield) was obtained as a white solid.
1H-NMR(400MHz,CDCl3):δ=6.56(d,4H)、6.68(t,2H)、6.94(t,8H)、7.01-7.02(m,18H)、7.10(s,1H)、7.15-7.19(m,17H). The structure of the compound obtained was confirmed by NMR spectrum.
1 H-NMR (400 MHz, CDCl 3 ): δ = 6.56 (d, 4 H), 6.68 (t, 2 H), 6.94 (t, 8 H), 7.01-7. 02 (m, 18H), 7.10 (s, 1 H), 7.15 to 7.19 (m, 17 H).
5,5-(1,3-フェニレンビス(サルファンジイル))ビス(N1,N1,N3,N3-テトラフェニルベンゼン-1,3-ジアミン)(0.29g、0.30mmol)およびオルトジクロロベンゼン(10ml)の入ったフラスコに、窒素雰囲気下、室温で、三臭化ホウ素(0.471g、1.2mmol)を加えた。滴下終了後、150℃まで昇温後4時間撹拌した。その後、再び室温まで冷却して、N-ジイソプロピルエチルアミン(0.63ml、3.6mmol)を加え、発熱が収まるまで撹拌した。その後減圧下、反応溶液を留去して粗生成物を得た。フロリジルを用いて得られた粗生成物を濾過し(溶離液:トルエン)、ろ液の溶媒を留去後、超音波粉砕機を用いアセトニトリルにて洗浄し、目的物である1,3-ビス(5,9-ジフェニル-5,9-ジヒドロ-5,9-ジアザ-13bボラナフト[3,2,1-de]アントラセン-7-イル)チオ)ベンゼン(30.3mg、収率10%)を黄色固体として得た。
5,5 (1,3-phenylene bis (monkey fan-diyl)) bis (N 1, N 1, N 3, N 3 - tetraphenyl-1,3-diamine) (0.29 g, 0.30 mmol) To a flask containing and and o-dichlorobenzene (10 ml) was added boron tribromide (0.471 g, 1.2 mmol) at room temperature under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was heated to 150 ° C. and stirred for 4 hours. Then, it was again cooled to room temperature, N-diisopropylethylamine (0.63 ml, 3.6 mmol) was added and stirred until the exotherm ceased. Thereafter, the reaction solution was distilled off under reduced pressure to obtain a crude product. The crude product obtained using Florisil is filtered (eluent: toluene), the solvent of the filtrate is distilled off, and the product is washed with acetonitrile using an ultrasonic crusher, and the desired
1H-NMR(400MHz,CDCl3):δ=5.76(s,4H)、6.70(d,4H)、7.06(t,1H)、7.06-7.08(m,3H)、7.20-7.27(m,14H)、7.38-7.47(m,8H)、7.54(t,8H)、8.91(d,4H). The structure of the compound obtained was confirmed by NMR spectrum.
1 H-NMR (400 MHz, CDCl 3 ): δ = 5.76 (s, 4 H), 6.70 (d, 4 H), 7.06 (t, 1 H), 7.06 to 7.08 (m, m) 3H), 7.20-7.27 (m, 14H), 7.38-7.47 (m, 8H), 7.54 (t, 8H), 8.91 (d, 4H).
化合物(1-5400):1,3-ビス(5,9-ジフェニル-5,9-ジヒドロ-5,9-ジアザ-13bボラナフト[3,2,1-de]アントラセン-7-イル)オキシ)ベンゼンの合成
Compound (1-5400): 1,3-bis (5,9-diphenyl-5,9-dihydro-5,9-diaza-13b boranaphtho [3,2,1-de] anthracene-7-yl) oxy) Synthesis of benzene
窒素雰囲気下、レゾルシノール(11.6g、105mmol)、1-ブロモ-3,5-ジクロロベンゼン(55.0g、221mmol)、炭酸カリウム(4.27g、31mmol)をN-メチル-2-ピロリドン(NMP)180mLへ溶解させ、そこへヨウ化銅(4.01g、21.1mmol)、トリス(2,4-ペンタンジオナト)鉄(III)(7.44g、21.1mmol)、トリフェニルホスフィン(22.1g、84.3mmol)を加え、180℃で4時間撹拌した後、反応液を冷却し、セライトでろ過した。ろ液を水で3回洗浄し、無水硫酸ナトリウムで乾燥した。得られた溶液を濃縮することで組成生物を得、得られた組成生物をシリカゲルクロマトグラフィー(トルエン)で精製し、その後、濃縮することで、1,3-ビス(3,5-ジクロロフェノキシ)ベンゼン(15.5g、収率37%)を無色液体として得た。
Under nitrogen atmosphere, resorcinol (11.6 g, 105 mmol), 1-bromo-3,5-dichlorobenzene (55.0 g, 221 mmol), potassium carbonate (4.27 g, 31 mmol) with N-methyl-2-pyrrolidone (NMP) ) Dissolved in 180 mL, into which copper iodide (4.01 g, 21.1 mmol), tris (2,4-pentanedionato) iron (III) (7.44 g, 21.1 mmol), triphenylphosphine (22) 1 g (84.3 mmol) was added, and after stirring for 4 hours at 180 ° C., the reaction solution was cooled and filtered through celite. The filtrate was washed three times with water and dried over anhydrous sodium sulfate. The solution obtained is concentrated to obtain a composition organism, and the composition organism obtained is purified by silica gel chromatography (toluene) and then concentrated to give 1,3-bis (3,5-dichlorophenoxy). Benzene (15.5 g, 37% yield) was obtained as a colorless liquid.
1H-NMR(400MHz,CDCl3):δ=6.71(t,1H)、6.83(dd,2H)、6.91(d,4H)、7.11(t,2H)、7.37(t,1H). The structure of the compound obtained was confirmed by NMR spectrum.
1 H-NMR (400 MHz, CDCl 3 ): δ = 6.71 (t, 1 H), 6.83 (dd, 2 H), 6.91 (d, 4 H), 7.11 (t, 2 H), 7 .37 (t, 1 H).
窒素雰囲気下、1,3-ビス(3,5-ジクロロフェノキシ)ベンゼン(14.5g、36.2mmol)、ジフェニルアミン(29.4g、174mmol)、Pd2(dba)3(1.66mg、1.81mmol)、トリ-tert-ブチルホスフィンテトラフルオロボラート(1.05g、3.62mmol)、NaOtBu(20.9g、217mmol)をトルエン300mLに溶解させ、110℃で8時間加熱撹拌した。反応液を室温まで冷却し、シリカゲルを用いて濾過し(溶離液:トルエン)、溶媒を減圧留去して粗生成物を得た。得られた粗生成物を混合溶媒(トルエン/ヘプタン=2/1(容量比))で再結晶し、5,5-(1,3-フェニレンビス(オキシ))ビス(N1,N1,N3,N3-テトラフェニルベンゼン-1,3-ジアミン)(18.8g、収率56%)を白色固体として得た。
Under a nitrogen atmosphere, 1,3-bis (3,5-dichlorophenoxy) benzene (14.5 g, 36.2 mmol), diphenylamine (29.4g, 174mmol), Pd 2 (dba) 3 (1.66mg, 1. 81 mmol), tri-tert-butylphosphine tetrafluoroborate (1.05 g, 3.62 mmol), NaOtBu (20.9 g, 217 mmol) were dissolved in 300 mL of toluene, and the mixture was heated and stirred at 110 ° C. for 8 hours. The reaction solution was cooled to room temperature, filtered through silica gel (eluent: toluene), and the solvent was evaporated under reduced pressure to give a crude product. The obtained crude product is recrystallized with a mixed solvent (toluene / heptane = 2/1 (volume ratio)) to give 5,5- (1,3-phenylenebis (oxy)) bis (N 1 , N 1 , 1 N 3 , N 3 -tetraphenylbenzene-1,3-diamine (18.8 g, 56% yield) was obtained as a white solid.
1H-NMR(400MHz,CDCl3):δ=6.30(d,4H)、6.51-55(m,3H)、6.58(t,2H)、6.95(t,8H)、7.07(d,16H)、7.19(t,16H)、7.27(t,1H). The structure of the compound obtained was confirmed by NMR spectrum.
1 H-NMR (400 MHz, CDCl 3 ): δ = 6.30 (d, 4 H), 6.51-55 (m, 3 H), 6.58 (t, 2 H), 6.95 (t, 8 H) , 7.07 (d, 16 H), 7.19 (t, 16 H), 7. 27 (t, 1 H).
5,5-(1,3-フェニレンビス(オキシ))ビス(N1,N1,N3,N3-テトラフェニルベンゼン-1,3-ジアミン)(1g、1.07mmol)およびオルトジクロロベンゼン(30ml)の入ったフラスコに、窒素雰囲気下、室温で、三臭化ホウ素ジクロロベンゼン溶液(2.15mL、2.0mol/L)を加えた。滴下終了後、150℃まで昇温後4時間撹拌した。その後、0度に冷却して、炭酸水素ナトリウム水溶液を加え、発熱が収まるまで撹拌した。その後、減圧下で反応溶液を留去して粗生成物を得た。得られた粗生成物をフロリジルを用いて濾過し(溶離液:トルエン)、ろ液の溶媒を留去後、超音波粉砕機を用いてアセトニトリルで洗浄し、化合物(1-5400)を黄色固体として得た。
5,5 (1,3-phenylene bis (oxy)) bis (N 1, N 1, N 3, N 3 - tetraphenyl-1,3-diamine) (1 g, 1.07 mmol) and ortho-dichlorobenzene To a flask containing (30 ml) was added boron tribromide dichlorobenzene solution (2.15 mL, 2.0 mol / L) at room temperature under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was heated to 150 ° C. and stirred for 4 hours. After cooling to 0 ° C., an aqueous solution of sodium hydrogen carbonate was added, and the mixture was stirred until heat generation ceased. Thereafter, the reaction solution was distilled off under reduced pressure to obtain a crude product. The obtained crude product is filtered using Florisil (eluent: toluene), and the solvent of the filtrate is distilled off, and then it is washed with acetonitrile using an ultrasonic grinder, and the compound (1-5400) is a yellow solid Got as.
<サンプルの準備>
化合物の吸収特性と発光特性(蛍光と燐光)を評価する方法としては、化合物を溶媒に溶解して溶媒中で評価する場合と薄膜状態で評価する場合がある。さらに、薄膜状態で評価する場合は、評価対象の化合物の有機EL素子における使用態様に応じて、評価対象の化合物のみを薄膜化し評価する場合と評価対象の化合物を適切なマトリックス材料中に分散して薄膜化して評価する場合がある。 (1) Evaluation method of basic physical properties
<Preparation of sample>
As a method of evaluating the absorption characteristics and the light emission characteristics (fluorescence and phosphorescence) of a compound, the compound may be dissolved in a solvent and evaluated in a solvent or in a thin film state. Furthermore, when evaluating in the thin film state, depending on the usage mode of the compound to be evaluated in the organic EL element, the compound to be evaluated is dispersed in an appropriate matrix material in the case of thin filming only the compound to be evaluated. And may be evaluated for thin film formation.
吸収スペクトルの測定は、紫外可視近赤外分光光度計((株)島津製作所、UV-2600)を用いて行った。また、蛍光スペクトルまたは燐光スペクトルの測定は、分光蛍光光度計(日立ハイテク(株)製、F-7000)を用いて行った。 <Evaluation of absorption characteristics and light emission characteristics>
The measurement of the absorption spectrum was performed using an ultraviolet visible near infrared spectrophotometer (UV-2600, manufactured by Shimadzu Corporation). Further, the measurement of the fluorescence spectrum or the phosphorescence spectrum was performed using a spectrofluorimeter (F-7000 manufactured by Hitachi High-Tech Co., Ltd.).
蛍光寿命測定装置(浜松ホトニクス(株)製、C11367-01)を用いて300Kで蛍光寿命を測定する。適切な励起波長で測定される極大発光波長において蛍光寿命の早い成分と遅い成分を観測する。蛍光を発光する一般的な有機EL材料の室温における蛍光寿命測定では、熱による3重項成分の失活により、燐光に由来する3重項成分が関与する遅い成分が観測されることはほとんどない。評価対象の化合物において遅い成分が観測された場合は、励起寿命の長い3重項エネルギーが熱活性化により1重項エネルギーに移動して遅延蛍光として観測されたことを示すことになる。 <Evaluation of fluorescence lifetime (delayed fluorescence)>
The fluorescence lifetime is measured at 300 K using a fluorescence lifetime measuring apparatus (C11367-01, manufactured by Hamamatsu Photonics Co., Ltd.). Observe the fast and slow components of the fluorescence lifetime at the maximum emission wavelength measured at the appropriate excitation wavelength. In fluorescence lifetime measurement at room temperature of a general organic EL material that emits fluorescence, due to the deactivation of the triplet component by heat, a slow component involving the triplet component derived from phosphorescence is hardly observed . When a slow component is observed in the compound to be evaluated, it indicates that triplet energy having a long excitation life is transferred to singlet energy by thermal activation and observed as delayed fluorescence.
吸収スペクトルの長波長末端A(nm)からEg=1240/Aで算出される。 <Calculation of energy gap (Eg)>
It is calculated by Eg = 1240 / A from the long wavelength terminal A (nm) of the absorption spectrum.
一重項励起エネルギー(ES)は、蛍光スペクトルの極大発光波長B(nm)からEs=1240/Bで算出される。また、三重項励起エネルギー(ET)は、燐光スペクトルの極大発光波長C(nm)からET=1240/Cで算出される。 < Calculation of E S , E T and Δ EST>
Singlet excitation energy (E S) is calculated by Es = 1240 / B from the maximum emission wavelength B of the fluorescence spectrum (nm). The triplet excitation energy (E T ) is calculated from E T = 1240 / C from the maximum emission wavelength C (nm) of the phosphorescence spectrum.
吸収スペクトルの測定は、化合物(1-201)を1重量%の濃度でPMMAに分散した薄膜形成基板(石英製)を準備して、行った。
蛍光スペクトルの測定は、化合物(1-201)を1重量%の濃度でPMMAに分散した薄膜形成基板(石英製)を準備し、励起波長340nmで励起してフォトルミネッセンスを測定した。その結果、極大発光波長は451nmであり、ESは2.75eVと算出された。また、同じ基板を準備し、励起波長400nmで励起して蛍光量子収率を測定したところ、79%と高い値であった。
燐光スペクトルの測定は、化合物(1-201)を1重量%の濃度でPMMAに分散した薄膜形成基板(石英製)を準備し、励起波長340nmで励起してフォトルミネッセンスを測定した。その結果、極大発光波長は492nmであり、ETは2.52eVと算出された。
以上の各スペクトルを図2に示す。 (2) Evaluation of basic physical properties of compound (1-201) The absorption spectrum is measured by preparing a thin film-formed substrate (made of quartz) in which compound (1-201) is dispersed in PMMA at a concentration of 1% by weight. The
For measurement of the fluorescence spectrum, a thin film-formed substrate (made of quartz) in which the compound (1-201) was dispersed in PMMA at a concentration of 1% by weight was prepared, and excited at an excitation wavelength of 340 nm to measure photoluminescence. As a result, the maximum emission wavelength was 451 nm, E S was calculated to 2.75 eV. In addition, when the same substrate was prepared and excited at an excitation wavelength of 400 nm and the fluorescence quantum yield was measured, it was a high value of 79%.
The phosphorescence spectrum was measured by preparing a thin film-formed substrate (made of quartz) in which the compound (1-201) was dispersed in PMMA at a concentration of 1% by weight, and excited at an excitation wavelength of 340 nm to measure photoluminescence. As a result, the maximum emission wavelength was 492 nm, E T was calculated to 2.52 eV.
Each of the above spectra is shown in FIG.
有機EL素子の評価項目としては、駆動電圧(V)、発光波長(nm)、CIE色度(x,y)、外部量子効率(%)、発光スペクトルの最大波長(nm)および半値幅(nm)等がある。これらの評価項目は、適切な発光輝度時の値を用いることができる。 (3) Evaluation method of organic EL element The evaluation items of the organic EL element include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum emission spectrum There are wavelength (nm) and half width (nm). As these evaluation items, values at appropriate light emission luminance can be used.
表1の層構成を有する有機EL素子を次の手順で作製することができる。まず、スパッタリングにより150nmの厚さに製膜したITO膜を有する26mm×28mm×0.7mmのガラス基板((株)厚木ミクロ製)を透明支持基板とする。この透明支持基板を市販の蒸着装置(長州産業(株)製)の基板ホルダーに固定し、HI-1(正孔注入層材料)、HAT-CN(正孔注入層材料)、HT-1(正孔輸送層材料)、HT-2(正孔輸送層材料)、EMH1(ホスト材料)、化合物(1-201)(ドーパント材料)、ET-1(電子輸送層材料)、ET-2(電子輸送層材料)、Liqをそれぞれ入れたモリブデン製蒸着用ボート、マグネシウムを入れたSiC製るつぼ、および銀を入れたSiC製るつぼを装着する。 (4) Evaluation of Organic EL Element Using Compound (1-201) as a Dopant The organic EL element having the layer configuration of Table 1 can be manufactured by the following procedure. First, a 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Atsugi Micro Co., Ltd.) having an ITO film formed to a thickness of 150 nm by sputtering is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (made by Choshu Sangyo Co., Ltd.), and HI-1 (hole injection layer material), HAT-CN (hole injection layer material), HT-1 (hole material). Hole transport layer material), HT-2 (hole transport layer material), EMH1 (host material), compound (1-201) (dopant material), ET-1 (electron transport layer material), ET-2 (electron Transport layer material), a molybdenum deposition boat containing Liq, a SiC crucible containing magnesium, and a SiC crucible containing silver are mounted.
化合物(1-201)を化合物(1-5400)に替えることで、上記と同様にして有機EL素子が得られ、各評価をすることができる。 (5) Evaluation of organic EL device using compound (1-5400) as dopant By replacing compound (1-201) with compound (1-5400), an organic EL device is obtained in the same manner as described above, and each evaluation You can
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 100
Claims (12)
- 2つの下記一般式(1)で表される部分構造と、当該2つの部分構造を連結する連結基L1とからなる二量体化合物であって、
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリール、アルキルまたはシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-R、>Sまたは>Seであり、前記>N-RのRは置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいアルキルまたは置換されていてもよいシクロアルキルであり、前記>N-RのRは連結基L2により前記A環、B環および/またはC環と結合していてもよい。)
式(1)で表される部分構造は、2つが同じ構造であっても異なった構造であってもよく、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~30のアリーレン、炭素数2~30のヘテロアリーレン、炭素数1~24のアルキレン、炭素数1~24のアルケニレン、炭素数1~24のアルキニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、前記>N-RのRは炭素数6~16のアリール、炭素数2~20のヘテロアリール、炭素数1~12のアルキルまたは炭素数3~16のシクロアルキルであり、連結基L1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2~20のヘテロアリール炭素数1~12のアルキルまたは炭素数3~16のシクロアルキルで置換されていてもよく、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい、二量体化合物。 A dimer compound comprising two partial structures represented by the following general formula (1) and a linking group L1 linking the two partial structures,
Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
Y 1 is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R in Si-R and Ge-R is aryl, alkyl or cycloalkyl; Yes,
X 1 and X 2 are each independently>O,>NR,> S or> Se, and R in> NR is optionally substituted aryl, which may be substituted Heteroaryl, alkyl which may be substituted, or cycloalkyl which may be substituted, wherein R in> N—R is connected to the A ring, B ring and / or C ring via a linking group L 2, It is also good. )
The partial structure represented by formula (1) may have the same structure or different structures from each other, provided that in the two partial structures, Y 1 is both B and X 1 and X 2 are both> The case of O is excluded, and the case where Y 1 is both P 共 に O, X 1 and X 2 are both> O is also excluded.
The linking group L 1 is a single bond, arylene having 6 to 30 carbon atoms, heteroarylene having 2 to 30 carbon atoms, alkylene having 1 to 24 carbon atoms, alkenylene having 1 to 24 carbon atoms, alkynylene having 1 to 24 carbon atoms, -R-, -S-,> N-R, or a combination thereof, wherein R in> N-R is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, or 1 to carbon atoms 12 alkyl or cycloalkyl having 3 to 16 carbon atoms, at least one hydrogen in the linking group L 1 is aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, alkyl or 1 to 12 carbons And may be substituted with 3 to 16 cycloalkyls,
The dimer compound in which at least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium. - 上記式(1)中、
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換または無置換のアリール、置換または無置換のヘテロアリール、置換または無置換のジアリールアミノ、置換または無置換のジヘテロアリールアミノ、置換または無置換のアリールヘテロアリールアミノ、置換または無置換のアルキル、置換または無置換のシクロアルキル、置換または無置換のアルコキシまたは置換または無置換のアリールオキシで置換されていてもよく、また、これらの環はY1、X1およびX2から構成される上記式中央の縮合2環構造と結合を共有する5員環または6員環を有し、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRはアリール、アルキルまたはシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-R、>Sまたは>Seであり、前記>N-RのRはアルキルまたはシクロアルキルで置換されていてもよいアリール、アルキルまたはシクロアルキルで置換されていてもよいヘテロアリール、アルキルまたはシクロアルキルであり、前記>N-RのRは-O-、-S-、-C(-R)2-および単結合から選択される連結基L2により前記A環、B環および/またはC環と結合していてもよく、前記-C(-R)2-のRは、水素、アルキルまたはシクロアルキルであり、そして、
式(1)で表される部分構造は、2つが同じ構造であっても異なった構造であってもよく、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~16のアリーレン、炭素数2~20のヘテロアリーレン、炭素数1~12のアルキレン、炭素数1~12のアルケニレン、炭素数1~12のアルキニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、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、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、連結基L1における少なくとも1つの水素は炭素数6~12のアリール、炭素数2~15のヘテロアリール、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルで置換されていてもよく、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい、
請求項1に記載する二量体化合物。 In the above formula (1),
Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted The ring may be substituted with unsubstituted aryloxy, and these rings may be 5- or 6-membered rings sharing a bond with the fused two-ring structure at the center of the above formula composed of Y 1 , X 1 and X 2 Have a ring,
Y 1 is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R in Si-R and Ge-R is aryl, alkyl or cycloalkyl; Yes,
X 1 and X 2 are each independently>O,>N—R,> S or> Se, wherein R in> N—R is aryl optionally substituted with alkyl or cycloalkyl Or heteroaryl, alkyl or cycloalkyl optionally substituted with cycloalkyl, wherein R in> N—R is selected from —O—, —S—, —C (—R) 2 — and a single bond A linking group L2 may bind to the ring A, ring B and / or ring C, R in -C (-R) 2- is hydrogen, alkyl or cycloalkyl, and
The partial structure represented by formula (1) may have the same structure or different structures from each other, provided that in the two partial structures, Y 1 is both B and X 1 and X 2 are both> The case of O is excluded, and the case where Y 1 is both P 共 に O, X 1 and X 2 are both> O is also excluded.
The linking group L 1 is a single bond, arylene having 6 to 16 carbon atoms, heteroarylene having 2 to 20 carbon atoms, alkylene having 1 to 12 carbon atoms, alkenylene having 1 to 12 carbon atoms, alkynylene having 1 to 12 carbon atoms, -R-, -S-,> N-R, or a combination thereof, wherein R in> N-R is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, or 1 to carbons 6 alkyl or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the linking group L 1 is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl or 1 to 6 carbons And may be substituted with several 3 to 14 cycloalkyls,
At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
A dimeric compound according to claim 1. - 上記部分構造が下記一般式(2)で表される、請求項1に記載する二量体化合物。
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11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、シクロアルキル、アルコキシ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、アルキルまたはシクロアルキルで置換されていてもよく、また、R1~R11のうちの隣接する基同士は結合してa環、b環またはc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、シクロアルキル、アルコキシ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、アルキルまたはシクロアルキルで置換されていてもよく、
Y1は、B、P、P=O、P=S、Al、Ga、As、Si-RまたはGe-Rであり、前記Si-RおよびGe-RのRは炭素数6~12のアリール、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-R、>Sまたは>Se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、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、前記>N-RのRは-O-、-S-、-C(-R)2-および単結合から選択される連結基L2により前記a環、b環および/またはc環と結合していてもよく、前記-C(-R)2-のRは炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、そして、
式(2)で表される部分構造は、2つが同じ構造であっても異なった構造であってもよく、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~12のアリーレン、炭素数2~15のヘテロアリーレン、炭素数1~6のアルキレン、炭素数1~6のアルケニレン、炭素数1~6のアルキニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、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、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルであり、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。 The dimer compound according to claim 1, wherein the partial structure is represented by the following general formula (2).
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylamino Heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and R 1 to Adjacent groups of R 11 may combine to form an aryl ring or heteroaryl ring with the a ring, b ring or c ring, and at least one hydrogen in the formed ring is aryl, heteroaryl , Diarylamino, diheteroarylamino, arylheteroarylamino, aru Le, cycloalkyl, may be substituted by alkoxy or aryloxy, at least one hydrogen in these aryl, heteroaryl, it may be substituted by alkyl or cycloalkyl,
Y 1 is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R in the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms , Alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons,
X 1 and X 2 are each independently>O,>NR,> S or> Se, wherein R in> NR is an aryl having 6 to 12 carbon atoms, and 2 to 15 carbon atoms Heteroaryl, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, wherein R in> N—R is selected from —O—, —S—, —C (—R) 2 — and a single bond The linking group L2 may be linked to the a ring, b ring and / or c ring, and R in -C (-R) 2- is alkyl having 1 to 6 carbons or 3 to 6 carbons 14 cycloalkyl and
The partial structure represented by Formula (2) may have the same structure or different structures from each other, provided that in the two partial structures, Y 1 is both B and X 1 and X 2 are both> The case of O is excluded, and the case where Y 1 is both P 共 に O, X 1 and X 2 are both> O is also excluded.
The linking group L 1 is a single bond, arylene having 6 to 12 carbon atoms, heteroarylene having 2 to 15 carbon atoms, alkylene having 1 to 6 carbon atoms, alkenylene having 1 to 6 carbon atoms, alkynylene having 1 to 6 carbon atoms, -R-, -S-,> N-R, or a combination thereof, wherein R in> N-R is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, or 1 to carbons 6 alkyl or cycloalkyl having 3 to 14 carbon atoms,
At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium. - 上記式(2)中、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11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、ジアリールアミノ(ただしアリールは炭素数6~12のアリール)、炭素数1~20のアルキルまたは炭素数3~20のシクロアルキルであり、また、R1~R11のうちの隣接する基同士は結合してa環、b環またはc環と共に炭素数9~16のアリール環または炭素数6~15の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つの水素は炭素数6~10のアリール、炭素数1~6のアルキルまたは炭素数3~14のシクロアルキルで置換されていてもよく、
Y1は、B、P、P=O、P=SまたはSi-Rであり、前記Si-RのRは炭素数6~10のアリール、炭素数1~4のアルキルまたは炭素数5~10のシクロアルキルであり、
X1およびX2は、それぞれ独立して、>O、>N-Rまたは>Sであり、前記>N-RのRは炭素数6~10のアリール、炭素数1~4のアルキルまたは炭素数5~10のシクロアルキルであり、そして、
式(2)で表される部分構造は、2つが同じ構造であり、ただし、2つの部分構造においてY1が共にB、X1およびX2が共に>Oの場合は除かれ、かつ、Y1が共にP=O、X1およびX2が共に>Oの場合も除かれ、
前記連結基L1は、単結合、炭素数6~12のアリーレン、炭素数1~6のアルキレン、炭素数1~6のアルケニレン、-O-、-S-、>N-R、または、これらの組み合わせであり、前記>N-RのRは炭素数6~10のアリールであり、
前記二量体化合物における少なくとも1つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい、
請求項3に記載する二量体化合物。 In the above formula (2),
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently hydrogen, aryl having 6 to 30 carbon atoms, carbon A heteroaryl of 2 to 30 and diarylamino (wherein aryl is aryl of 6 to 12 carbons), alkyl of 1 to 20 carbons or cycloalkyl of 3 to 20 carbons, and R 1 to R 11 And the adjacent groups may combine to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring or c ring; At least one hydrogen may be substituted with aryl having 6 to 10 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons,
Y 1 is B, P, P = O, P = S or Si—R, and R in the above Si—R is aryl having 6 to 10 carbons, alkyl having 1 to 4 carbons, or 5 to 10 carbons Cycloalkyl, and
X 1 and X 2 are each independently>O,> N—R or> S, and R in> N—R is aryl having 6 to 10 carbons, alkyl having 1 to 4 carbons or carbon Several 5-10 cycloalkyls, and
In the partial structure represented by the formula (2), two are the same structure, provided that in the two partial structures Y 1 is both B and X 1 and X 2 are both> O, and Y is Also when 1 is both P = O, X 1 and X 2 are both> O,
The linking group L 1 is a single bond, an arylene having 6 to 12 carbon atoms, an alkylene having 1 to 6 carbon atoms, an alkenylene having 1 to 6 carbon atoms, -O-, -S-,> NR, or Which is a combination, and in the above> N—R, R is aryl having 6 to 10 carbon atoms,
At least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.
A dimeric compound according to claim 3. - 請求項1ないし5のいずれかに記載する二量体化合物を含有する、有機デバイス用材料。 A material for an organic device comprising the dimer compound according to any one of claims 1 to 5.
- 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6に記載する有機デバイス用材料。 The material for an organic device according to claim 6, wherein the material for an organic device is a material for an organic electroluminescent device, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
- 発光層用材料である、請求項7に記載する有機電界発光素子用材料。 The material for an organic electroluminescent element according to claim 7, which is a material for a light emitting layer.
- 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8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。 An organic electroluminescent device comprising: a pair of electrodes comprising an anode and a cathode; and a light emitting layer disposed between the pair of electrodes and containing the material for a light emitting layer according to claim 8.
- 前記陰極と前記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9に記載する有機電界発光素子。 It has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer comprises quinolinol metal complex, pyridine derivative, phenanthroline derivative The organic electroluminescent device according to claim 9, comprising at least one selected from the group consisting of borane derivatives and benzimidazole derivatives.
- 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10に記載の有機電界発光素子。 The electron transport layer and / or the electron injection layer may further be selected from alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, and alkaline earth metals. The at least one selected from the group consisting of halides, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals. The organic electroluminescent element as described in 10.
- 請求項9~11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または照明装置。 A display or illumination device comprising the organic electroluminescent device according to any one of claims 9 to 11.
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112028918A (en) * | 2019-12-31 | 2020-12-04 | 陕西莱特光电材料股份有限公司 | Organic compound, application thereof and organic electroluminescent device |
CN112028913A (en) * | 2019-06-03 | 2020-12-04 | 北京鼎材科技有限公司 | Novel boron-containing organic electroluminescent material and application thereof |
KR20210009289A (en) * | 2019-07-16 | 2021-01-26 | 주식회사 엘지화학 | Compound, coating composition comprising the same, and organic light emitting device using the same |
US20210036227A1 (en) * | 2019-07-30 | 2021-02-04 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
WO2021122740A1 (en) | 2019-12-19 | 2021-06-24 | Merck Patent Gmbh | Polycyclic compounds for organic electroluminescent devices |
Families Citing this family (1)
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---|---|---|---|---|
KR20220064474A (en) | 2020-11-11 | 2022-05-19 | 삼성디스플레이 주식회사 | Light emitting device |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016219487A (en) * | 2015-05-15 | 2016-12-22 | コニカミノルタ株式会社 | Organic electroluminescent element, display device, illuminating device, organic electroluminescent element material and novel compound |
WO2017018326A1 (en) * | 2015-07-24 | 2017-02-02 | コニカミノルタ株式会社 | Organic electroluminescent element, display device, and illumination device |
JP2017079267A (en) * | 2015-10-20 | 2017-04-27 | コニカミノルタ株式会社 | Organic electroluminescent element, method of manufacturing organic electroluminescent element, display device, lighting device, and organic electroluminescent element material |
WO2017092495A1 (en) * | 2015-12-04 | 2017-06-08 | 广州华睿光电材料有限公司 | Thermal excitation delay fluorescent materials, polymer, mixture, composition, and organic electronic device |
JP2018043984A (en) * | 2016-09-07 | 2018-03-22 | 学校法人関西学院 | Polycyclic aromatic compound |
WO2018074167A1 (en) * | 2016-10-18 | 2018-04-26 | コニカミノルタ株式会社 | Organic borane complex, composition containing organic borane, and organic electroluminescent element |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3735703B2 (en) | 1999-12-21 | 2006-01-18 | 大阪大学長 | Electroluminescence element |
US20040131881A1 (en) | 2002-12-31 | 2004-07-08 | Eastman Kodak Company | Complex fluorene-containing compounds for use in OLED devices |
JP2005170911A (en) | 2003-12-15 | 2005-06-30 | Idemitsu Kosan Co Ltd | Aromatic compound and organic electroluminescent element using the same |
DE102010009903A1 (en) | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Connections for electronic devices |
WO2012118164A1 (en) | 2011-03-03 | 2012-09-07 | 国立大学法人九州大学 | Novel compound, charge transport material, and organic device |
TWI636056B (en) | 2014-02-18 | 2018-09-21 | 學校法人關西學院 | Polycyclic aromatic compound and method for production the same, material for organic device and application thereof |
JP6696971B2 (en) * | 2015-03-25 | 2020-05-20 | 学校法人関西学院 | Polycyclic aromatic compound and composition for forming light emitting layer |
CN110225917B (en) * | 2017-05-02 | 2022-11-25 | 株式会社Lg化学 | Novel compound and organic light emitting device using the same |
-
2018
- 2018-10-12 KR KR1020207013646A patent/KR102633062B1/en active IP Right Grant
- 2018-10-12 CN CN201880066816.0A patent/CN111212844B/en active Active
- 2018-10-12 WO PCT/JP2018/038086 patent/WO2019074093A1/en active Application Filing
- 2018-10-12 JP JP2019548254A patent/JP7276750B2/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016219487A (en) * | 2015-05-15 | 2016-12-22 | コニカミノルタ株式会社 | Organic electroluminescent element, display device, illuminating device, organic electroluminescent element material and novel compound |
WO2017018326A1 (en) * | 2015-07-24 | 2017-02-02 | コニカミノルタ株式会社 | Organic electroluminescent element, display device, and illumination device |
JP2017079267A (en) * | 2015-10-20 | 2017-04-27 | コニカミノルタ株式会社 | Organic electroluminescent element, method of manufacturing organic electroluminescent element, display device, lighting device, and organic electroluminescent element material |
WO2017092495A1 (en) * | 2015-12-04 | 2017-06-08 | 广州华睿光电材料有限公司 | Thermal excitation delay fluorescent materials, polymer, mixture, composition, and organic electronic device |
JP2018043984A (en) * | 2016-09-07 | 2018-03-22 | 学校法人関西学院 | Polycyclic aromatic compound |
WO2018074167A1 (en) * | 2016-10-18 | 2018-04-26 | コニカミノルタ株式会社 | Organic borane complex, composition containing organic borane, and organic electroluminescent element |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112028913A (en) * | 2019-06-03 | 2020-12-04 | 北京鼎材科技有限公司 | Novel boron-containing organic electroluminescent material and application thereof |
CN112028913B (en) * | 2019-06-03 | 2023-12-05 | 北京鼎材科技有限公司 | Novel boron-containing organic electroluminescent material and application thereof |
KR20210009289A (en) * | 2019-07-16 | 2021-01-26 | 주식회사 엘지화학 | Compound, coating composition comprising the same, and organic light emitting device using the same |
KR102412786B1 (en) | 2019-07-16 | 2022-06-24 | 주식회사 엘지화학 | Compound, coating composition comprising the same, and organic light emitting device using the same |
US20210036227A1 (en) * | 2019-07-30 | 2021-02-04 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
WO2021122740A1 (en) | 2019-12-19 | 2021-06-24 | Merck Patent Gmbh | Polycyclic compounds for organic electroluminescent devices |
CN112028918A (en) * | 2019-12-31 | 2020-12-04 | 陕西莱特光电材料股份有限公司 | Organic compound, application thereof and organic electroluminescent device |
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