WO2020020602A1 - Organic molecules for optoelectronic devices - Google Patents
Organic molecules for optoelectronic devices Download PDFInfo
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- WO2020020602A1 WO2020020602A1 PCT/EP2019/068082 EP2019068082W WO2020020602A1 WO 2020020602 A1 WO2020020602 A1 WO 2020020602A1 EP 2019068082 W EP2019068082 W EP 2019068082W WO 2020020602 A1 WO2020020602 A1 WO 2020020602A1
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- WO
- WIPO (PCT)
- Prior art keywords
- optionally substituted
- substituents
- group
- deuterium
- independently
- Prior art date
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- 230000005693 optoelectronics Effects 0.000 title claims abstract description 35
- 125000001424 substituent group Chemical group 0.000 claims abstract description 176
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 76
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 54
- 229910052805 deuterium Inorganic materials 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 22
- 125000003367 polycyclic group Chemical group 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 125000002950 monocyclic group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 125000004306 triazinyl group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 8
- 229910052705 radium Inorganic materials 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000001771 vacuum deposition Methods 0.000 claims description 3
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 110
- -1 n- butyl Chemical group 0.000 description 63
- 238000004770 highest occupied molecular orbital Methods 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 28
- 238000000295 emission spectrum Methods 0.000 description 26
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 24
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 23
- 239000004926 polymethyl methacrylate Substances 0.000 description 23
- 238000006862 quantum yield reaction Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000005259 measurement Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000005424 photoluminescence Methods 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 241000202702 Adeno-associated virus - 3 Species 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 6
- IOPQERQQZZREDR-UHFFFAOYSA-N 1-bromo-3,5-diphenylbenzene Chemical group C=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 IOPQERQQZZREDR-UHFFFAOYSA-N 0.000 description 6
- MMNNWKCYXNXWBG-UHFFFAOYSA-N 2,4,6-tris(3-phenylphenyl)-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=CC=CC(C=2N=C(N=C(N=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 MMNNWKCYXNXWBG-UHFFFAOYSA-N 0.000 description 6
- YEWVLWWLYHXZLZ-UHFFFAOYSA-N 9-(3-dibenzofuran-2-ylphenyl)carbazole Chemical compound C1=CC=C2C3=CC(C=4C=CC=C(C=4)N4C5=CC=CC=C5C5=CC=CC=C54)=CC=C3OC2=C1 YEWVLWWLYHXZLZ-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000002484 cyclic voltammetry Methods 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000005620 boronic acid group Chemical group 0.000 description 5
- 150000001716 carbazoles Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000001161 time-correlated single photon counting Methods 0.000 description 5
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 4
- 0 *c(cc1)cc(c2c3ccc(*)c2)c1[n]3-c(c(-c(c(-c1ccccc1)cc(-c1ccccc1)c1)c1-c1ccccc1)c1)ccc1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound *c(cc1)cc(c2c3ccc(*)c2)c1[n]3-c(c(-c(c(-c1ccccc1)cc(-c1ccccc1)c1)c1-c1ccccc1)c1)ccc1-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 0.000 description 4
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 239000011970 polystyrene sulfonate Substances 0.000 description 4
- 229960002796 polystyrene sulfonate Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 3
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 3
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 3
- PWJYOTPKLOICJK-UHFFFAOYSA-N 2-methyl-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(C)C=C3NC2=C1 PWJYOTPKLOICJK-UHFFFAOYSA-N 0.000 description 3
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical group CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 3
- WPUSEOSICYGUEW-UHFFFAOYSA-N 4-[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WPUSEOSICYGUEW-UHFFFAOYSA-N 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- ZLHINBZEEMIWIR-UHFFFAOYSA-N 9-(3-dibenzothiophen-2-ylphenyl)carbazole Chemical compound C1=CC=C2C3=CC(C=4C=CC=C(C=4)N4C5=CC=CC=C5C5=CC=CC=C54)=CC=C3SC2=C1 ZLHINBZEEMIWIR-UHFFFAOYSA-N 0.000 description 3
- WHMHUGLMCAFKFE-UHFFFAOYSA-N 9-[3,5-di(dibenzofuran-2-yl)phenyl]carbazole Chemical compound C1=CC=C2C3=CC(C=4C=C(C=C(C=4)N4C5=CC=CC=C5C5=CC=CC=C54)C4=CC=C5OC=6C(C5=C4)=CC=CC=6)=CC=C3OC2=C1 WHMHUGLMCAFKFE-UHFFFAOYSA-N 0.000 description 3
- XVBYZOSXOUDFKJ-UHFFFAOYSA-N 9-[3,5-di(dibenzothiophen-2-yl)phenyl]carbazole Chemical compound C1=C(C=CC=2SC3=C(C=21)C=CC=C3)C=1C=C(C=C(C=1)C1=CC2=C(SC3=C2C=CC=C3)C=C1)N1C2=CC=CC=C2C=2C=CC=CC1=2 XVBYZOSXOUDFKJ-UHFFFAOYSA-N 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- WIHKEPSYODOQJR-UHFFFAOYSA-N [9-(4-tert-butylphenyl)-6-triphenylsilylcarbazol-3-yl]-triphenylsilane Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C2=CC=C([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2C2=CC([Si](C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C21 WIHKEPSYODOQJR-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000011152 fibreglass Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000012736 patent blue V Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- WJDZZXIDQYKVDG-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C(Cl)=C1 WJDZZXIDQYKVDG-UHFFFAOYSA-N 0.000 description 2
- TXBFHHYSJNVGBX-UHFFFAOYSA-N (4-diphenylphosphorylphenyl)-triphenylsilane Chemical compound C=1C=CC=CC=1P(C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 TXBFHHYSJNVGBX-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- FQABTURRFUZZBZ-UHFFFAOYSA-N 2,4,6-tris(9,9'-spirobi[fluorene]-2-yl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C1=C2)C3=CC=CC=C3C1=CC=C2C1=NC(C=2C=C3C4(C5=CC=CC=C5C5=CC=CC=C54)C4=CC=CC=C4C3=CC=2)=NC(C2=CC=C3C4=CC=CC=C4C4(C3=C2)C2=CC=CC=C2C=2C4=CC=CC=2)=N1 FQABTURRFUZZBZ-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
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- 229910052723 transition metal Chemical class 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices.
- the object of the present invention is to provide molecules which are suitable for use in optoelectronic devices.
- the invention provides a new class of organic molecules.
- the organic molecules of the invention are purely organic molecules, i.e. they do not contain any metal ions.
- the organic molecules of the invention are free of metal atoms or metal ions.
- the organic molecules may, however, include metalloids, in particular, B, Si, Sn, Se, and/or Ge.
- the organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range.
- the organic molecules exhibit in particular emission maxima between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm.
- the photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 20% or more.
- the molecules according to the invention exhibit in particular thermally activated delayed fluorescence (TADF).
- TADF thermally activated delayed fluorescence
- Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color.
- organic light-emitting molecules of the invention comprise or consist of a structure of Formula I,
- Q is selected from the group consisting of N and C-R Py ;
- T, V, W, X, Y is independently from each other selected from the group consisting of R 1 and phenyl, which is optionally substituted with one or more substituents R 2 .
- R Tz is at each occurrence independently from another selected from the group consisting of hydrogen
- R Py is at each occurrence independently from another selected from the group consisting of hydrogen
- R 1 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium,
- R 2 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium,
- R a , R 3 and R 4 are at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , CN, F, Br, I, Ci-C 4 o-alkyl, which is optionally substituted with one or more substituents R 5 and
- a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring- closure with one or more of the other substituents selected from the group consisting of R a , R 3 , R 4 and R 5 .
- R 5 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , 0S0 2 R 6 , CF 3 , CN, F, Br, I,
- a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring- closure with one or more of the other substituents selected from the group consisting of R a , R 3 , R 4 and R 5 .
- R 6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F,
- Ci-C5-alkoxy wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;
- the substituents from the group consisting of R a , R 3 , R 4 or R 5 independently from each other form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more of the other (remaining) substituents selected from the group consisting of R a , R 3 , R 4 or R 5 .
- R a , R 3 and R 4 are at each occurrence independently from another selected to be a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system together with one or more of the other substituents R a , R 3 , R 4 and/or R 5 within the organic molecule, it is preferred for R a , R 3 and R 4 to form the mono- or polycyclic, aliphatic, aromatic and/or benzo- fused ring system with a substituent R a , R 3 , R 4 or R 5 that is positioned adjacent to it in the ring.
- R a , R 3 and R 4 it is more preferred in certain embodiments for R a , R 3 and R 4 to form the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system including at least one or more rings with a ring size of 5 to 8 atoms.
- the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system described above may itself comprise at least one substituent R 5 .
- substituent R 5 is at each occurrence and independently from another selected to form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more of the other substituents R a , R 3 , R 4 or R 5 within the organic molecule; it is preferred for R 5 to form the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with an immediately ring-adjacent substituent selected from the group consisting of R a , R 3 , R 4 and R 5 .
- substituents R a , R 3 , R 4 or R 5 independently from each other form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents of the other substituents R a , R 3 , R 4 or R 5 , it contains at least one atom selected from the group consisting of N, S and O.
- R 5 forms the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system including at least one or more rings with a ring of a size of 5 to 8 atoms.
- the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system includes at least one (one, two, etc.) aromatic rings.
- the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system itself comprises at least one substituent R 5 .
- At least one ring member Q is N
- At least one substituent selected from the group consisting of T, V, W, X and Y is phenyl which is optionally substituted with one or more substituents R 2 , and
- W is hydrogen (H).
- R 1 is hydrogen at each occurrence.
- R 2 is hydrogen at each occurrence.
- R 1 and R 2 is hydrogen at each occurrence.
- Z is a direct bond.
- exactly one substituent selected from the group consisting of T, V, W, X and Y is phenyl.
- exactly two substituents selected from the group consisting of T, V, W, X and Y are phenyl.
- exactly three substituents selected from the group consisting of T, V, W, X and Y are phenyl.
- exactly four substituents selected from the group consisting of T, V, W, X and Y are phenyl.
- W is hydrogen (H).
- T is phenyl
- V is phenyl
- W is phenyl
- V and X is phenyl
- T, W and Y is phenyl
- R Tz is at each occurrence independently from each other Ce-Cis-aryl
- R Tz is at each occurrence independently from each other phenyl
- R Tz is, at each occurrence independently from each other, phenyl,
- R Tz is at each occurrence independently from each other phenyl
- R Tz is at each occurrence independently from each other phenyl
- R Tz is phenyl at each occurrence.
- R 1 , R 2 and R Py is hydrogen at each occurrence.
- R 1 and R 2 is hydrogen at each occurrence and R Tz is phenyl at each occurrence.
- the organic light-emitting molecules of the invention consist of a structure of Formula lla:
- Y* and W # is H, T # , V # and X # is independently from each other selected from the group consisting of H and phenyl, which is optionally substituted with one or more substituents R 2 ;
- At least one substituent selected from the group consisting of T # , V # , and X # is phenyl which is optionally substituted with one or more substituents R 2 ;
- the organic molecules of the invention comprise or consist of a structure of Formula llaa:
- T # , V # , and X # is independently from each other selected from the group consisting of H and phenyl
- At least one substituent selected from the group consisting of T # , V # , and X # is phenyl and for the other substituents any one of the aforementioned definitions apply.
- R a is at each occurrence independently from another selected from the group consisting of: H,
- Me, Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- R a is at each occurrence independently from another selected from the group consisting of H,
- Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph.
- R a is at each occurrence independently from another selected from the group consisting of: H,
- Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- R a is H at each occurrence.
- At least one R a is not H.
- the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lib, Formula llb-2, Formula llb-3, and Formula llb-4:
- R b is at each occurrence independently from another selected from the group consisting of: deuterium,
- the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lib. In an additional embodiment of the invention, the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lie, Formula llc-2, Formula llc-3, and Formula llc-4:
- the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lie.
- R b is at each occurrence independently from another selected from the group consisting of:
- Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyrimidyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- R b is at each occurrence independently from another selected from the group consisting of:
- Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph
- triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph.
- R b is at each occurrence independently from another selected from the group consisting of:
- Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 , and Ph,
- R a and R 5 is at each occurrence independently from another selected from the group consisting of: hydrogen (H), deuterium (D), methyl (Me), i-propyl (CH(CH 3 ) 2 ) (’Pr), t-butyl fBu), phenyl (Ph), CN, CF 3 , and diphenylamine (NPfi 2 ).
- the organic molecules comprise or consist of a structure of Formula III:
- 0-5 refers to an integer, i.e. to the numbers 0, 1 , 2, 3, 4, and 5.
- the organic molecules comprise or consist of a structure of Formula III and R Tz is Ph.
- the organic molecules comprise or consist of a structure selected from the group of Formula MI-1 , Formula MI-2 and Formula MI-3:
- the organic molecules comprise or consist of a structure selected from the group consisting of Formula llla-1 , Formula llla-2 and Formula llla-3:
- R c is at each occurrence independently from another selected from the group consisting of: deuterium,
- Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF3, and Ph;
- pyridinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF3, and Ph;
- pyrimidinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF3, and Ph;
- carbazolyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF3, and Ph;
- triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF3, and Ph;
- the organic molecules comprise or consist of a structure selected from the group of Formula lllb-1 , Formula lllb-2 and Formula II lb-3:
- the organic molecules comprise or consist of a structure of Formula IV:
- the organic molecules comprise or consist of a structure selected from the group of Formula IV-1 , Formula IV-2 and Formula IV-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula IVa-1 , Formula IVa-2 and Formula IVa-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula IVb-1 , Formula IVb-2 and Formula IVb-3:
- the organic molecules comprise or consist of a structure of Formula V:
- the organic molecules comprise or consist of a structure selected from the group of Formula V-1 , Formula V- 2 and Formula V-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Va-1 , Formula Va-2 and Formula Va-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Vb-1 , Formula Vb-2 and Formula Vb-3:
- the organic molecules comprise or consist of a structure of Formula VI:
- the organic molecules comprise or consist of a structure selected from the group of Formula VI-1 , Formula VI-2 and Formula VI-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Vla-1 , Formula Vla-2 and Formula Vla-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Vlb-1 , Formula Vlb-2 and Formula Vlb-3:
- the organic molecules comprise or consist of a structure of Formula VII:
- the organic molecules comprise or consist of a structure selected from the group of Formula VI 1-1 , Formula VII-2 and Formula VII-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Vllla-1 , Formula VII la-2 and Formula VII la-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Vlllb-1 , Formula VII lb-2 and Formula VII lb-3:
- the organic molecules comprise or consist of a structure of Formula VIII:
- the organic molecules comprise or consist of a structure selected from the group of Formula VIII-1 , Formula VIII-2 and Formula VIII-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Vllla-1 , Formula Vllla-2 and Formula Vllla-3:
- the organic molecules comprise or consist of a structure selected from the group of Formula Vlllb-1 , Formula Vlllb-2 and Formula Vlllb-3:
- Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 and Ph; and
- triazinyl which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, l Bu, CN, CF 3 and Ph.
- aryl and aromatic may be understood in the broadest sense as any mono-, bi- or polycyclic aromatic moieties. Accordingly, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom. Notwithstanding, throughout the application the number of aromatic ring atoms may be given as subscripted number in the definition of certain substituents. In particular, the heteroaromatic ring includes one to three heteroatoms.
- heteroaryl and“heteroaromatic” may be understood in the broadest sense as any mono-, bi- or polycyclic hetero-aromatic moieties that include at least one heteroatom.
- the heteroatoms may at each occurrence be the same or different and be individually selected from the group consisting of N, O and S.
- arylene refers to a divalent substituent that bears two binding sites to other molecular structures and thereby serving as a linker structure.
- a group in the exemplary embodiments is defined differently from the definitions given here, for example, the number of aromatic ring atoms or number of heteroatoms differs from the given definition, the definition in the exemplary embodiments is to be applied.
- a condensed (annulated) aromatic or heteroaromatic polycycle is built of two or more single aromatic or heteroaromatic cycles, which formed the polycycle via a condensation reaction.
- aryl group or heteroaryl group comprises groups which can be bound via any position of the aromatic or heteroaromatic group, derived from benzene, naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, pheno
- cyclic group may be understood in the broadest sense as any mono-, bi- or polycyclic moieties.
- biphenyl as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is defined in regard to the binding site to another chemical moiety.
- alkyl group may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent.
- the term alkyl comprises the substituents methyl (Me), ethyl (Et), n-propyl ( n Pr), i-propyl ('Pr), cyclopropyl, n- butyl ( n Bu), i-butyl ('Bu), s-butyl ( s Bu), t-butyl fBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1 -methyl (Me), ethy
- alkenyl comprises linear, branched, and cyclic alkenyl substituents.
- alkenyl group exemplarily comprises the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
- alkynyl comprises linear, branched, and cyclic alkynyl substituents.
- alkynyl group exemplarily comprises ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
- alkoxy comprises linear, branched, and cyclic alkoxy substituents.
- alkoxy group exemplarily comprises methoxy, ethoxy, n- propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.
- thioalkoxy comprises linear, branched, and cyclic thioalkoxy substituents, in which the O of the exemplarily alkoxy groups is replaced by S.
- halogen and“halo” may be understood in the broadest sense as being preferably fluorine, chlorine, bromine or iodine.
- the organic molecules according to the invention have an excited state lifetime of not more than 150 ps, of not more than 100 ps, in particular of not more than 50 ps, more preferably of not more than 10 ps or not more than 7 ps in a film of poly(methyl methacrylate) (PMMA) with 10 % by weight of organic molecule at room temperature.
- PMMA poly(methyl methacrylate)
- the organic molecules according to the invention represent thermally-activated delayed fluorescence (TADF) emitters, which exhibit a AEST value, which corresponds to the energy difference between the first excited singlet state (S1 ) and the first excited triplet state (T1 ), of less than 5000 cm 1 , preferably less than 3000 cm 1 , more preferably less than 1500 cm 1 , even more preferably less than 1000 cm 1 or even less than 500 cm 1 .
- TADF thermally-activated delayed fluorescence
- the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E is larger than -6.2 eV, preferably larger than -6.0 eV, more preferably larger than -5.9 eV, even more preferably larger than -5.8 eV, wherein E HOMO (E) is determined by cyclic voltammetry.
- the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E is larger than -5.8 eV, wherein E HOMO (E) is determined by cyclic voltammetry.
- the organic molecules according to the invention have an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, with a full width at half maximum of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or even less than 0.40 eV in a film of poly(methyl methacrylate) (PMMA) with 10 % by weight of organic molecule at room temperature.
- PMMA poly(methyl methacrylate)
- the organic molecules according to the invention have a“blue material index” (BMI), calculated by dividing the photoluminescence quantum yield (PLQY) in % by the CIEy color coordinate of the emitted light, of more than 150, in particular more than 200, preferably more than 250, more preferably of more than 300 or even more than 500.
- BMI blue material index
- Orbital and excited state energies can be determined either by means of experimental methods or by calculations employing quantum-chemical methods, in particular density functional theory calculations.
- the energy of the highest occupied molecular orbital E HOMO is determined by methods known to the person skilled in the art from cyclic voltammetry measurements with an accuracy of 0.1 eV. The cyclic voltammetry measurement methods are described in the experimental section.
- the energy of the lowest unoccupied molecular orbital E LUMO is calculated as E HOMO + E gap , wherein E gap is determined as follows: For host compounds, the onset of the emission spectrum of a film with 10 % by weight of host in poly(methyl methacrylate) (PMMA) is used as E gap , unless stated otherwise. For emitter molecules, E gap is determined as the energy at which the excitation and emission spectra of a film with 10% by weight of emitter in PMMA cross.
- the energy of the first excited triplet state T 1 is determined from the onset of the emission spectrum at low temperature, typically at 77 K.
- the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K, if not otherwise stated measured in a film of PMMA with 10% by weight of emitter.
- the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum, if not otherwise stated measured in a film of PMMA with 10% by weight of host or emitter compound.
- a further aspect of the invention relates to a process for preparing organic molecules (with an optional subsequent reaction) according to the invention, wherein a R 1 -, R 2 -substituted Hal 3 - fluoropyridine is used as a reactant:
- a 1-fluorobenzene EO-2 which is substituted with a coupling group CG 2 in 4-position and which is substituted with a coupling group CG 3 in 3-position, is used as a reactant, which is reacted with the heterocycle E0-1 , which is substituted with a coupling group Hal 3 (reactant E0-1 ).
- the coupling groups Hal 3 and CG 2 are chosen as a reaction pair to introduce the heterocycle of EO-2 at the position of CG 2 .
- coupling groups CG 3 and CG 4 are chosen as reaction pair for introducing the heterocycle E0-4 at the position of CG 3 .
- a so-called Suzuki coupling reaction is used.
- CG 2 is a boronic acid group or a boronic acid ester group, in particular a boronic acid pinacol ester group
- Hal 3 is chosen from Cl, Br or I.
- CG 3 is chosen from Cl, Br or I
- CG 4 is a boronic acid group or a boronic acid ester group, in particular a boronic acid pinacol ester group
- CG 3 is a boronic acid group or a boronic acid ester group, in particular a boronic acid pinacol ester group
- CG 4 is chosen from Cl, Br or I.
- An alternative synthesis route comprises the introduction of a nitrogen heterocycle via copper- or palladium-catalyzed coupling to an aryl halide or aryl pseudohalide, preferably an aryl bromide, an aryl iodide, aryl triflate or an aryl tosylate.
- Pd 2 (dba) 3 tris(dibenzylideneacetone)dipalladium(O)
- the ligand may be selected from the group consisting of S-Phos ([2-dicyclohexylphoshino-2’,6’-dimethoxy-1 ,1’-biphenyl]), X-Phos (2- (dicyclohexylphosphino)-2”,4”,6”-triisopropylbiphenyl), and P(Cy)3 (tricyclohexylphosphine).
- the salt is, for example, selected from tribasic potassium phosphate and potassium acetate and the solvent can be a pure solvent, such as toluene or dioxane, or a mixture, such as toluene/dioxane/water or dioxane/toluene.
- a person of skill in the art can determine which Pd catalyst, ligand, salt and solvent combination will result in high reaction yields.
- typical conditions include the use of a base, such as tribasic potassium phosphate or sodium hydride, for example, in an aprotic polar solvent, such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF), for example.
- a base such as tribasic potassium phosphate or sodium hydride
- an aprotic polar solvent such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF), for example.
- a further aspect of the invention relates to the use of an organic molecule according to the invention as a luminescent emitter or as an absorber, and/or as host material and/or as electron transport material, and/or as hole injection material, and/or as hole blocking material in an optoelectronic device, in particular as a luminescent emitter.
- the optoelectronic device may be understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or nearest ultraviolet (UV) range, i.e. , in the range of a wavelength of from 380 to 800 nm. More preferably, the optoelectronic device may be able to emit light in the visible range, i.e., of from 400 to 800 nm.
- UV visible or nearest ultraviolet
- the optoelectronic device is more particularly selected from the group consisting of:
- OLEDs organic light-emitting diodes
- the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
- OLED organic light emitting diode
- LEC light emitting electrochemical cell
- the fraction of the organic molecule according to the invention in the emission layer in an optoelectronic device, more particularly in OLEDs is 1 % to 99 % by weight, more particularly 5 % to 80 % by weight. In an alternative embodiment, the proportion of the organic molecule in the emission layer is 100 % by weight.
- the light-emitting layer comprises not only the organic molecules according to the invention but also a host material whose triplet (T1 ) and singlet (S1 ) energy levels are energetically higher than the triplet (T 1 ) and singlet (S1 ) energy levels of the organic molecule.
- a further aspect of the invention relates to a composition
- a composition comprising or consisting of:
- the light-emitting layer EML comprises or consists of a composition comprising or consisting of:
- the light-emitting layer EML comprises or) consists of a composition comprising or consisting of:
- energy can be transferred from the host compound H to the one or more organic molecules according to the invention E, in particular transferred from the first excited triplet state T1 (H) of the host compound H to the first excited triplet state T1 (E) of the one or more organic molecules according to the invention E and/ orfrom the first excited singlet state S1 (H) of the host compound H to the first excited singlet state S1 (E) of the one or more organic molecules according to the invention E.
- the light-emitting layer EML comprises or (essentially) consists of a composition comprising or consisting of:
- the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) in the range of from -5 to -6.5 eV and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy E HOMO (D), wherein E HOMO (H) > E HOMO (D).
- the host compound H has a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H) and the at least one further host compound D has a lowest unoccupied molecular orbital LUMO(D) having an energy E LUMO (D), wherein E LUMO (H)
- the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) and a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H), and
- the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy E HOMO (D) and a lowest unoccupied molecular orbital LUMO(D) having an energy E LUMO (D),
- the organic molecule according to the invention E has a highest occupied molecular orbital HOMO(E) having an energy E HOMO (E) and a lowest unoccupied molecular orbital LUMO(E) having an energy E LUMO (E),
- > ⁇ HOMO ⁇ and the difference between the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E (E HOMO (E)) and the energy level of the highest occupied molecular orbital HOMO(H) of the host compound H (E HOMO (H)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV or even between -0.1 eV and 0.1 eV; and EL U M O
- the invention relates to an optoelectronic device comprising an organic molecule or a composition of the type described here, more particularly in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor, more particularly gas and vapour sensors not hermetically externally shielded, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.
- OLED organic light-emitting diode
- OLED sensor more particularly gas and vapour sensors not hermetically externally shielded
- organic diode organic solar cell
- organic transistor organic field-effect transistor
- organic laser and down-conversion element organic laser and down-conversion element
- the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
- OLED organic light emitting diode
- LEC light emitting electrochemical cell
- the organic molecule according to the invention E is used as emission material in a light-emitting layer EML.
- the light-emitting layer EML consists of the composition according to the invention described here.
- the optoelectronic device when the optoelectronic device is an OLED, it may exhibit the following layer structure:
- cathode layer wherein the OLED comprises each layer only optionally, except for the EML, which is mandatory.
- different layers may be merged and the OLED may comprise more than one layer of each layer type as defined above.
- the optoelectronic device may optionally comprise one or more protective layers protecting the device from damaging exposure to harmful species in the environment including, exemplarily moisture, vapor and/or gases.
- the optoelectronic device is an OLED, which exhibits the following inverted layer structure:
- anode layer A wherein the OLED with an inverted layer structure comprises each layer other than the emitting layer B only optionally.
- different layers may be merged and the OLED may comprise more than one layer of each layer types defined above.
- the optoelectronic device is an OLED, which may exhibit stacked architecture.
- this architecture contrary to the typical arrangement, where the OLEDs are placed side by side, the individual units are stacked on top of each other.
- Blended light may be generated with OLEDs exhibiting a stacked architecture, in particular white light may be generated by stacking blue, green and red OLEDs.
- the OLED exhibiting a stacked architecture may optionally comprise a charge generation layer (CGL), which is typically located between two OLED subunits and typically consists of a n-doped and p-doped layer with the n-doped layer of one CGL being typically located closer to the anode layer.
- CGL charge generation layer
- the optoelectronic device is an OLED, which comprises two or more emission layers between anode and cathode.
- this so-called tandem OLED comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light and one emission layer emits blue light, and optionally may comprise further layers such as charge generation layers, blocking or transporting layers between the individual emission layers.
- the emission layers are adjacently stacked.
- the tandem OLED comprises a charge generation layer between each two emission layers.
- adjacent emission layers or emission layers separated by a charge generation layer may be merged.
- the substrate may be formed by any material or composition of materials. Most frequently, glass slides are used as substrates. Alternatively, thin metal layers (e.g., copper, gold, silver or aluminum films) or plastic films or slides may be used. This may allow a higher degree of flexibility.
- the anode layer A is mostly composed of materials allowing to obtain an (essentially) transparent film. As at least one of both electrodes should be (essentially) transparent in order to allow light emission from the OLED, either the anode layer A or the cathode layer C is transparent.
- the anode layer A comprises a large content or even consists of transparent conductive oxides (TCOs).
- Such anode layer A may exemplarily comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, wolfram oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or doped polythiophene.
- the anode layer A (essentially) consists of indium tin oxide (ITO) (e.g., (ln0 3 )0.9(Sn0 2 )0.1 ).
- ITO indium tin oxide
- TCOs transparent conductive oxides
- HIL hole injection layer
- the HIL may facilitate the injection of quasi charge carriers (i.e., holes) in that the transport of the quasi charge carriers from the TCO to the hole transport layer (HTL) is facilitated.
- the hole injection layer may comprise poly-3, 4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS), M0O2, V2O5, CuPC or Cul, in particular a mixture of PEDOT and PSS.
- the hole injection layer (HIL) may also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL).
- the HIL may exemplarily comprise PEDOT:PSS (poly-3, 4- ethylendioxy thiophene: polystyrene sulfonate), PEDOT (poly-3, 4-ethylendioxy thiophene), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2, 2', 7,7'- tetrakis(n,n-diphenylamino)-9,9’-spirobifluorene), DNTPD (N 1 ,NT-(biphenyl-4,4'-diyl)bis(N1 - phenyl-N4,N4-di-m-tolylbenzene-1 ,4-diamine), NPB (N,N'-nis-(1 -naphthalenyl)-N,N'-bis- phenyl-(1 ,T-bipheny
- HTL hole transport layer
- any hole transport compound may be used.
- electron-rich heteroaromatic compounds such as triarylamines and/or carbazoles may be used as hole transport compound.
- the HTL may decrease the energy barrier between the anode layer A and the light-emitting layer EML.
- the hole transport layer (HTL) may also be an electron blocking layer (EBL).
- EBL electron blocking layer
- hole transport compounds bear comparably high energy levels of their triplet states T 1.
- the hole transport layer may comprise a star- shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4- butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4 - cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA (4,4',4"-tris[2- naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT- CN and/or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole).
- TCTA tris(4-
- the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix.
- Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may exemplarily be used as inorganic dopant.
- Tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), copper-pentafluorobenzoate (Cu(l)pFBz) or transition metal complexes may exemplarily be used as organic dopant.
- the EBL may exemplarily comprise mCP (1 ,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-Butylphenyl)-3,6- bis(triphenylsilyl)-9H-carbazole), and/or DCB (N,N'-dicarbazolyl-1 ,4-dimethylbenzene).
- the light-emitting layer EML Adjacent to the hole transport layer (HTL), typically, the light-emitting layer EML is located.
- the light-emitting layer EML comprises at least one light emitting molecule.
- the EML comprises at least one light emitting molecule according to the invention E.
- the light-emitting layer comprises only the organic molecules according to the invention E.
- the EML additionally comprises one or more host materials H.
- the host material H is selected from CBP (4,4'-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, SiMCP (3,5-Di(9H-carbazol-9- yl)phenyl]triphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2- (diphenylphosphino)phenyl] ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3
- the EML comprises a so-called mixed-host system with at least one hole-dominant host and one electron-dominant host.
- the EML comprises exactly one light emitting molecule according to the invention E and a mixed-host system comprising T2T as electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]- 9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2- dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H- carbazole as hole-dominant host.
- the EML comprises 50-80 % by weight, preferably 60-75 % by weight of a host selected from CBP, mCP, mCBP, 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45 % by weight, preferably 15-30 % by weight of T2T and 5-40 % by weight, preferably 10-30 % by weight of light emitting molecule according to the invention.
- a host selected from CBP, mCP, mCBP
- an electron transport layer Adjacent to the light-emitting layer EML an electron transport layer (ETL) may be located.
- ETL electron transport layer
- any electron transporter may be used.
- electron-poor compounds such as, e.g., benzimidazoles, pyridines, triazoles, oxadiazoles (e.g., 1 ,3,4-oxadiazole), phosphinoxides and sulfone, may be used.
- An electron transporter may also be a star-shaped heterocycle such as 1 , 3, 5-tri(1 -phenyl-1 H-benzo[d]imidazol-2-yl)phenyl (TPBi).
- the ETL may comprise NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1 ,10-phenanthroline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSP01 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(2,2'-bipyridin-5-yl)triphenyle), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1 ,3-bis[3,5-di(pyridin-3- yl)phenyl]benzene) and/or BTB (4,4 -bis-[2-(4,6-diphenyl-1 ,3,5-triazinyl)]-1 ,1 '-
- a cathode layer C Adjacent to the electron transport layer (ETL), a cathode layer C may be located.
- the cathode layer C may comprise or may consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy.
- the cathode layer may also consist of (essentially) non-transparent metals such as Mg, Ca or Al.
- the cathode layer C may also comprise graphite and or carbon nanotubes (CNTs).
- the cathode layer C may also consist of nanoscalic silver wires.
- An OLED may further, optionally, comprise a protection layer between the electron transport layer (ETL) and the cathode layer C (which may be designated as electron injection layer (EIL)).
- This layer may comprise lithium fluoride, cesium fluoride, silver, Liq (8- hydroxyquinolinolatolithium), LhO, BaF 2 , MgO and/or NaF.
- the electron transport layer (ETL) and/or a hole blocking layer (HBL) may comprise one or more host compounds H.
- the light-emitting layer EML may further comprise one or more further emitter molecules F.
- an emitter molecule F may be any emitter molecule known in the art.
- an emitter molecule F is a molecule with a structure differing from the structure of the molecules according to the invention E.
- the emitter molecule F may optionally be a TADF emitter.
- the emitter molecule F may optionally be a fluorescent and/or phosphorescent emitter molecule which is able to shift the emission spectrum and/or the absorption spectrum of the light-emitting layer EML.
- the triplet and/or singlet excitons may be transferred from the emitter molecule according to the invention E to the emitter molecule F before relaxing to the ground state SO by emitting light typically red-shifted in comparison to the light emitted by emitter molecule E.
- the emitter molecule F may also provoke two-photon effects (i.e., the absorption of two photons of half the energy of the absorption maximum).
- an optoelectronic device e.g., an OLED
- an OLED may exemplarily be an essentially white optoelectronic device.
- Exemplarily such white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and/or red light. Then, there may also optionally be energy transmittance between two or more molecules as described above.
- the designation of the colors of emitted and/or absorbed light is as follows: violet: wavelength range of >380-420 nm;
- deep blue wavelength range of >420-480 nm
- sky blue wavelength range of >480-500 nm
- red wavelength range of >620-800 nm.
- a deep blue emitter has an emission maximum in the range of from >420 to 480 nm
- a sky blue emitter has an emission maximum in the range of from >480 to 500 nm
- a green emitter has an emission maximum in a range of from >500 to 560 nm
- a red emitter has an emission maximum in a range of from >620 to 800 nm.
- a deep blue emitter may preferably have an emission maximum of below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.
- a further aspect of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m 2 of more than 8 %, more preferably of more than 10 %, more preferably of more than 13 %, even more preferably of more than 15 % or even more than 20 % and/or exhibits an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm and/or exhibits a LT80 value at 500 cd/m 2 of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h or even more than 1000 h.
- a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20 or even more preferably less than 0.15 or even less than 0.10.
- a further aspect of the present invention relates to an OLED, which emits light at a distinct color point.
- the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)).
- FWHM full width at half maximum
- the OLED according to the invention emits light with a FWHM of the main emission peak of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or even less than 0.40 eV.
- UHD Ultra High Definition
- a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and/ or a a CIEy color coordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.
- the invention relates to a method for producing an optoelectronic component.
- an organic molecule of the invention is used.
- the optoelectronic device in particular the OLED according to the present invention can be produced by any means of vapor deposition and/or liquid processing. Accordingly, at least one layer is
- Another aspect of the present invention relates to a process for producing an optoelectronic device, wherein an organic molecule or composition according to the invention is used, in particular comprising the processing of the organic molecule or of the composition by a vacuum evaporation method or from a solution.
- Further steps used to produce the optoelectronic device, in particular the OLED according to the present invention comprise depositing different layers individually and successively on a suitable substrate by means of subsequent deposition processes.
- the individual layers may be deposited using the same or differing deposition methods.
- Vapor deposition processes exemplarily comprise thermal (co)evaporation, chemical vapor deposition and physical vapor deposition.
- an AMOLED backplane is used as substrate.
- the individual layer may be processed from solutions or dispersions employing adequate solvents.
- Solution deposition process exemplarily comprise spin coating, dip coating and jet printing.
- Liquid processing may optionally be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere) and the solvent may optionally be completely or partially removed by means known in the state of the art. Examples
- 3-chloro-4-fluorophenylboronic acid pinacol ester (1.00 equivalents), 2-chloro-4,6-diphenyl- 1 ,3,5-triazine (CAS 3842-55-5; 1.00 equivalents), Tetrakis(triphenylphosphine)palladium(0) (0.03 equivalents), and potassium carbonate (3.00 equivalents) are stirred under nitrogen atmosphere in a THF/water mixture (ratio of 2:1 ) at 80 °C for 16 h. After cooling down to room temperature (rt), the mixture is filtered through a fiber glass filter, the filter cake successively washed with water and acetone and the filtrate discarded. The residue is collected, dried in vacuo and used without further purification (yield: 92%).
- the product E0-32I reacts further with 5 ' -Bromo-m-terphenyl (CAS: 103068-20-8) (1.00 equivalents), tetrakis(triphenylphosphine)palladium(0) (0.1 equivalent) and potassium carbonate (3.00 equivalents) are stirred under nitrogen atmosphere in a tetrahydrofuran (THF)/water mixture (ratio of 10:1 ) at 75 °C for 16 h. After cooling down to room temperature (rt), the reaction mixture is poured into water, the product is filtered and washed with ethanol (EtOH).
- THF tetrahydrofuran
- EtOH ethanol
- the donor molecule D-H is a 3,6-substituted carbazole (e.g., 3,6- dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g., 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1 ,8-substituted carbazole (e.g., 1 ,8-dimethylcarbazole, 1 ,8-diphenylcarbazole, 1 ,8-di-tert- butylcarbazole), a 1 -substituted carbazole (e.g., 1 -methylcarbazole, 1 -phenylcarbazole, 1 -tert- butylcarbazole), a 2-substituted carb
- halogen-substituted carbazole particularly 3-bromocarbazole
- D-H halogen-substituted carbazole
- a boronic acid ester functional group or boronic acid functional group may be, for example, introduced at the position of the one or more halogen substituents, which was introduced via D-H, to yield the corresponding carbazol-3-ylboronic acid ester or carbazol- 3-ylboronic acid, e.g., via the reaction with bis(pinacolato)diboron (CAS No. 73183-34-3).
- one or more substituents R a may be introduced in place of the boronic acid ester group or the boronic acid group via a coupling reaction with the corresponding halogenated reactant R a -Hal, preferably R a -CI and R a -Br.
- one or more substituents R a may be introduced at the position of the one or more halogen substituents, which was introduced via D-H, via the reaction with a boronic acid of the substituent R a [R a -B(OH)2] or a corresponding boronic acid ester.
- Cyclic voltammograms are measured from solutions having concentration of 10 3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate).
- the measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp2/FeCp2 + as internal standard.
- the HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).
- Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods.
- Orbital and excited state energies are calculated with the B3LYP functional.
- Def2-SVP basis sets and a m4-grid for numerical integration are used.
- the Turbomole program package is used for all calculations.
- the sample concentration is 1 mg/ml, dissolved in a suitable solvent.
- Photoluminescence spectroscopy and TCSPC Time-correlated single-photon counting Steady-state emission spectroscopy is measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.
- Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Y von TCSPC hub.
- NanoLED 370 (wavelength: 371 nm, puls duration: 1 ,1 ns)
- NanoLED 290 (wavelength: 294 nm, puls duration: ⁇ 1 ns)
- SpectraLED 355 (wavelength: 355 nm).
- Data analysis is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.
- Time-resolved PL measurements were performed on a FS5 fluorescence spectrometer from Edinburgh Instruments. Compared to measurements on the HORIBA setup, better light gathering allows for an optimized signal to noise ratio, which favors the FS5 system especially for transient PL measurements of delayed fluorescence characteristics.
- the FS5 consists of a xenon lamp providing a broad spectrum.
- the continuous light source is a 150W xenon arc lamp, selected wavelengths are chosen by a Czerny-Turner monochromator, which is also used to set specific emission wavelengths.
- the sample emission is directed towards a sensitive R928P photomultiplier tube (PMT), allowing the detection of single photons with a peak quantum efficiency of up to 25 % in the spectral range between 200 nm to 870 nm.
- the detector is a temperature stabilized PMT, providing dark counts below 300 cps (counts per second).
- a tail fit using three exponential functions is applied. By weighting the specific lifetimes t* with their corresponding amplitudes A i
- the delayed fluorescence lifetime T DF is determined.
- Emission maxima are given in nm, quantum yields F in % and CIE coordinates as x,y values.
- PLQY is determined using the following protocol:
- Excitation wavelength the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength
- n Photon denotes the photon count and Int. the intensity.
- OLED devices comprising organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight- percentage of one or more compounds is given in %. The total weight-percentage values amount to 100 %, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100 %.
- the not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current.
- the OLED device lifetime is extracted from the change of the luminance during operation at constant current density.
- the LT50 value corresponds to the time, where the measured luminance decreased to 50 % of the initial luminance
- analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80 % of the initial luminance
- LT 95 to the time point at which the measured luminance decreased to 95 % of the initial luminance etc.
- LT80 values at 500 cd/m 2 are determined using the following equation: wherein Lo denotes the initial luminance at the applied current density.
- the values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.
- HPLC-MS analysis is performed on an HPLC by Agilent (1 100 series) with MS-detector (Thermo LTQ XL).
- Exemplary a typical HPLC method is as follows: a reverse phase column 4,6mm x 150mm, particle size 3,5 pm from Agilent (ZORBAX Eclipse Plus 95A C18, 4.6 x 150 mm, 3.5 pm HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) following gradients
- Ionization of the probe is performed using an APCI (atmospheric pressure chemical ionization) source either in positive (APCI +) or negative (APCI -) ionization mode.
- APCI atmospheric pressure chemical ionization
- Example 1 was synthesized according to
- Figure 1 depicts the emission spectrum of Example 1 (10 % by weight in PMMA).
- the emission maximum (A max ) is at 462 nm.
- the photoluminescence quantum yield (PLQY) is 77 %, the full width at half maximum (FWHM) is 0.41 eV.
- the resulting CIE X coordinate is determined at 0.15 and the CIE y coordinate at 0.17.
- the HOMO(E) is -5.87 eV.
- Example 2 was synthesized according to AAV1-1 (yield 92%),
- Figure 2 depicts the emission spectrum of Example 2 (10 % by weight in PMMA).
- the emission maximum (A max ) is at 453 nm.
- the photoluminescence quantum yield (PLQY) is 76 %, the full width at half maximum (FWHM) is 0.43 eV.
- the resulting CIE X coordinate is determined at 0.15 and the CIE y coordinate at 0.14 and HOMO(E) is -5.89 eV.
- Example 3 was synthesized according to
- HPLC-LCMS Figure 3 depicts the emission spectrum of Example 3 (10 % by weight in PMMA).
- the emission maximum (A max ) is at 454 nm.
- the photoluminescence quantum yield (PLQY) is 68 %, the full width at half maximum (FWHM) is 0.43 eV.
- the resulting CIE X coordinate is determined at 0.15 and the CIE y coordinate at 0.15.
- the energy level of the highest occupied molecular orbital HOMO(E) is -5.93 eV.
- Example 3 was synthesized according to
- Figure 4 depicts the emission spectrum of Example 4 (10 % by weight in PMMA).
- the emission maximum (A max ) is at 444 nm.
- the photoluminescence quantum yield (PLQY) is 55 %, the full width at half maximum (FWHM) is 0.45 eV.
- the resulting CIE X coordinate is determined at 0.15 and the CIE y coordinate at 0.12.
- Example 5
- Example 5 was synthesized according to
- AAV2-3 (yield 84 %), wherein 5’-bromo-m-terphenyl (CAS 103068-20-8) was used as reactant EO-42, and
- Figure 5 depicts the emission spectrum of Example 5 (10 % by weight in PMMA).
- the emission maximum (A max ) is at 427 nm.
- the photoluminescence quantum yield (PLQY) is 32 %, the full width at half maximum (FWHM) is 0.46 eV.
- the resulting CIE X coordinate is determined at 0.16 and the CIE y coordinate at 0.08.
- Example 6 was synthesized according to
- Figure 6 depicts the emission spectrum of Example 6 (10 % by weight in PMMA).
- the emission maximum (A max ) is at 444 nm.
- the photoluminescence quantum yield (PLQY) is 66 %, the full width at half maximum (FWHM) is 0.44 eV.
- the resulting CIE X coordinate is determined at 0.15 and the CIE y coordinate at 0.1 1 .
- the energy level of the highest occupied molecular orbital HOMO(E) is -5.85 eV.
- Example 7 Example 7
- Example 7 was synthesized according to
- Figure 7 depicts the emission spectrum of Example 7 (10 % by weight in PMMA).
- the emission maximum (A max ) is at 453 nm.
- the photoluminescence quantum yield (PLQY) is 76 %, the full width at half maximum (FWHM) is 0.43 eV.
- the resulting CIE X coordinate is determined at 0.15 and the CIE y coordinate at 0.14.
- the energy level of the highest occupied molecular orbital HOMO(E) is -5.89 eV.
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Abstract
The invention relates to an organic compound, in particular for the use in optoelectronic devices. According to the invention, the organic compound has a structure of formula I, wherein Q is selected from the group consisting of N and C-RPy; T, V, W, X, Y is independently from each other selected from the group consisting of R1 and phenyl, which is optionally substituted with one or more substituents R2; at least one substituent selected from the group consisting of T, V, W, X and Y is phenyl which is optionally substituted with one or more substituents R2; and at least one ring member Q is N.
Description
ORGANIC MOLECULES
FOR OPTOELECTRONIC DEVICES
The invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices.
Description
The object of the present invention is to provide molecules which are suitable for use in optoelectronic devices.
This object is achieved by the invention which provides a new class of organic molecules. in contrast to metal complexes known for the use in optoelectronic devices, the organic molecules of the invention are purely organic molecules, i.e. they do not contain any metal ions. The organic molecules of the invention are free of metal atoms or metal ions. The organic molecules may, however, include metalloids, in particular, B, Si, Sn, Se, and/or Ge.
According to the present invention, the organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range. The organic molecules exhibit in particular emission maxima between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm. The photoluminescence quantum yields of the organic molecules according to the invention are, in particular, 20% or more. The molecules according to the invention exhibit in particular thermally activated delayed fluorescence (TADF). The use of the molecules according to the invention in an optoelectronic device, for example, an organic light-emitting diode (OLED), leads to higher efficiencies of the device. Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color.
The organic light-emitting molecules of the invention comprise or consist of a structure of Formula I,
Formula I
Q is selected from the group consisting of N and C-RPy;
T, V, W, X, Y is independently from each other selected from the group consisting of R1 and phenyl, which is optionally substituted with one or more substituents R2.
RTz is at each occurrence independently from another selected from the group consisting of hydrogen,
deuterium,
Ci-C5-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
Ce-Cis-aryl,
which is optionally substituted with one or more substituents R5; and
C3-Ci7-heteroaryl,
which is optionally substituted with one or more substituents R5.
RPy is at each occurrence independently from another selected from the group consisting of hydrogen,
deuterium,
Ci-C5-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
Ce-Cis-aryl,
which is optionally substituted with one or more substituents R6; and
C3-Ci7-heteroaryl,
which is optionally substituted with one or more substituents R6.
R1 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium,
Ci-C5-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and Ce-Cis-aryl,
which is optionally substituted with one or more substituents R6;
R2 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium,
Ci-C5-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and Ce-Cis-aryl,
which is optionally substituted with one or more substituents R6;
Z is selected from the group consisting of a direct bond, CR3R4, C=CR3R4, C=0, C=NR3, NR3, O, SiR3R4, S, S(O) and S(0)2;
Ra, R3 and R4 are at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, OSO2R5, CF3, CN, F, Br, I, Ci-C4o-alkyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-alkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-thioalkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkenyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkynyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ce-Ceo-aryl,
which is optionally substituted with one or more substituents R5;
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring- closure with one or more of the other substituents selected from the group consisting of Ra, R3, R4 and R5.
R5 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R6)2, OR6, Si(R6)3, B(OR6)2, 0S02R6, CF3, CN, F, Br, I,
Ci-C4o-alkyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
Ci-C4o-alkoxy,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
Ci-C4o-thioalkoxy,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
C2-C4o-alkenyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
C2-C4o-alkynyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
Ce-Ceo-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R6; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring- closure with one or more of the other substituents selected from the group consisting of Ra, R3, R4 and R5.
R6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF3, CN, F,
Ci-C5-alkyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Ci-C5-alkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Ci-Cs-thioalkoxy,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl,
wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF3, or F;
Ce-Cis-aryl,
which is optionally substituted with one or more C-i-Cs-alkyl substituents;
C3-Ci7-heteroaryl,
which is optionally substituted with one or more C-i-Cs-alkyl substituents;
N(C6-Ci8-aryl)2,
N(C3-Ci7-heteroaryl)2; and
N(C3-Ci7-heteroaryl)(C6-Ci8-aryl).
Optionally, the substituents from the group consisting of Ra, R3, R4 or R5 independently from each other form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more of the other (remaining) substituents selected from the group consisting of Ra, R3, R4 or R5.
If the substituents Ra, R3 and R4 are at each occurrence independently from another selected to be a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system together with one or more of the other substituents Ra, R3, R4 and/or R5 within the organic molecule, it is preferred for Ra, R3 and R4 to form the mono- or polycyclic, aliphatic, aromatic and/or benzo- fused ring system with a substituent Ra, R3, R4 or R5 that is positioned adjacent to it in the ring.
Furthermore, it is more preferred in certain embodiments for Ra, R3 and R4 to form the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system including at least one or more rings with a ring size of 5 to 8 atoms.
Moreover, it is preferred for the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system described above to include at least one or more aromatic rings.
In certain embodiments, the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system mentioned above and herein may itself comprise at least one substituent R5.
If the substituent R5 is at each occurrence and independently from another selected to form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more of the other substituents Ra, R3, R4 or R5 within the organic molecule; it is preferred for R5 to form the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with an immediately ring-adjacent substituent selected from the group consisting of Ra, R3, R4 and R5.
If the substituents Ra, R3, R4 or R5 independently from each other form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents of the other substituents Ra, R3, R4 or R5, it contains at least one atom selected from the group consisting of N, S and O.
Furthermore, in certain embodiments, R5 forms the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system including at least one or more rings with a ring of a size of 5 to 8 atoms.
Additionally, in certain embodiments of the organic molecule, the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system includes at least one (one, two, etc.) aromatic rings.
In further embodiments, the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system itself comprises at least one substituent R5.
Moreover, at least one ring member Q is N,
at least one substituent selected from the group consisting of T, V, W, X and Y is phenyl which is optionally substituted with one or more substituents R2, and
if exactly one substituent selected from the group consisting of T and Y is phenyl, W is hydrogen (H).
In one embodiment of the invention, R1 is hydrogen at each occurrence.
In one embodiment of the invention, R2 is hydrogen at each occurrence.
In one embodiment of the invention, R1 and R2 is hydrogen at each occurrence.
In one embodiment of the invention, Z is a direct bond.
In one embodiment of the invention, exactly one substituent selected from the group consisting of T, V, W, X and Y is phenyl.
In one embodiment of the invention, exactly two substituents selected from the group consisting of T, V, W, X and Y are phenyl.
In one embodiment of the invention, exactly three substituents selected from the group consisting of T, V, W, X and Y are phenyl.
In one embodiment of the invention, exactly four substituents selected from the group consisting of T, V, W, X and Y are phenyl.
In one embodiment of the invention, if exactly one substituent selected from the group consisting of T and Y is phenyl, which is optionally substituted with one or more substituents R2,
W is hydrogen (H).
In one embodiment of the invention, T is phenyl.
In one embodiment of the invention, V is phenyl.
In one embodiment of the invention, W is phenyl.
In one embodiment of the invention, V and X is phenyl.
In one embodiment of the invention, T, W and Y is phenyl.
In one embodiment of the invention, RTz is at each occurrence independently from each other Ce-Cis-aryl,
which is optionally substituted with one or more substituents R5.
In one embodiment of the invention, RTz is at each occurrence independently from each other phenyl,
which is optionally substituted with one or more substituents R5.
In one embodiment of the invention, RTz is, at each occurrence independently from each other, phenyl,
which is optionally substituted with one or more tert-butyl substituents or one or more Si(R6)3 substituents.
In one embodiment of the invention, RTz is at each occurrence independently from each other phenyl,
which is optionally substituted with one or more tert-butyl substituents.
In one embodiment of the invention, RTz is at each occurrence independently from each other phenyl,
which is optionally substituted with two tert-butyl substituents.
In one embodiment of the invention, RTz is phenyl at each occurrence.
In one embodiment of the invention, R1, R2 and RPy is hydrogen at each occurrence.
In one embodiment of the invention, R1 and R2 is hydrogen at each occurrence and RTz is phenyl at each occurrence.
In a further embodiment of the invention, the organic light-emitting molecules of the invention consist of a structure of Formula lla:
Formula lla
wherein
Y* and W# is H,
T#, V# and X# is independently from each other selected from the group consisting of H and phenyl, which is optionally substituted with one or more substituents R2;
wherein
at least one substituent selected from the group consisting of T#, V#, and X# is phenyl which is optionally substituted with one or more substituents R2; and
for the other substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules of the invention comprise or consist of a structure of Formula llaa:
Formula llaa
wherein
W# and Y# is H,
T#, V#, and X# is independently from each other selected from the group consisting of H and phenyl
wherein
at least one substituent selected from the group consisting of T#, V#, and X# is phenyl and for the other substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, Ra is at each occurrence independently from another selected from the group consisting of: H,
Me,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
and N(Ph)2.
In a further embodiment of the invention, Ra is at each occurrence independently from another selected from the group consisting of H,
Me,
'Pr,
lBu,
CN,
CF3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph.
In a further embodiment of the invention, Ra is at each occurrence independently from another selected from the group consisting of: H,
Me,
lBu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph.
In a further embodiment of the invention, Ra is H at each occurrence.
In a further embodiment of the invention, at least one Ra is not H.
In a further embodiment of the invention, the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lib, Formula llb-2, Formula llb-3, and Formula llb-4:
Formula llb-3 Formula llb-4
wherein
Rb is at each occurrence independently from another selected from the group consisting of: deuterium,
N(R5)2,
OR5,
Si(R5)3,
B(OR5)2,
OSO2R5,
CFs,
CN,
F,
Br,
I,
Ci-C4o-alkyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-alkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-thioalkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkenyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkynyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ce-Ceo-aryl,
which is optionally substituted with one or more substituents R5; and
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5;
for the other variables, the aforementioned definitions apply.
In a preferred embodiment of the invention, the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lib.
In an additional embodiment of the invention, the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lie, Formula llc-2, Formula llc-3, and Formula llc-4:
Formula llc-3 Formula llc-4
wherein the aforementioned definitions apply.
In a preferred embodiment of the invention, the organic light-emitting molecules of the invention consist of a structure selected from the group consisting of Formula lie.
In a further embodiment of the invention, Rb is at each occurrence independently from another selected from the group consisting of:
Me,
CN,
CFs,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyrimidyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
and N(Ph)2.
In a further embodiment of the invention, Rb is at each occurrence independently from another selected from the group consisting of:
Me,
'Pr,
lBu,
CN,
CF3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph.
In a further embodiment of the invention, Rb is at each occurrence independently from another selected from the group consisting of:
Me,
lBu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph,
triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph.
In the following, exemplary embodiments of the organic light-emitting molecules of the invention are shown:
In one embodiment, Ra and R5 is at each occurrence independently from another selected from the group consisting of: hydrogen (H), deuterium (D), methyl (Me), i-propyl (CH(CH3)2) (’Pr), t-butyl fBu), phenyl (Ph), CN, CF3, and diphenylamine (NPfi2).
In one embodiment of the invention, the organic molecules comprise or consist of a structure of Formula III:
Formula III
wherein for the substituents any one of the aforementioned definition applies.“0-5” refers to an integer, i.e. to the numbers 0, 1 , 2, 3, 4, and 5.
In another embodiment of the invention, the organic molecules comprise or consist of a structure of Formula III and RTz is Ph.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula MI-1 , Formula MI-2 and Formula MI-3:
Formula 111-1 Formula III-2 Formula MI-3
wherein is RIN for the substituents any one of the aforementioned definition applies.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group consisting of Formula llla-1 , Formula llla-2 and Formula llla-3:
Formula llla-1 Formula llla-2 Formula llla-3
wherein
Rc is at each occurrence independently from another selected from the group consisting of: deuterium,
Me,
iPr,
lBu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph;
pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph;
pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph;
carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph;
triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph;
and N(Ph)2.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula lllb-1 , Formula lllb-2 and Formula II lb-3:
Formula lllb-1 Formula lllb-2 Formula lllb-3
wherein for Rc any one of the aforementioned definitions apply.
In one embodiment of the invention, the organic molecules comprise or consist of a structure of Formula IV:
Formula IV
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula IV-1 , Formula IV-2 and Formula IV-3:
Formula IV-1 Formula IV-2 Formula IV-3
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula IVa-1 , Formula IVa-2 and Formula IVa-3:
wherein for Rc any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula IVb-1 , Formula IVb-2 and Formula IVb-3:
Formula IVb-1 Formula IVb-2 Formula IVb-3 wherein for Rc any one of the aforementioned definitions applies.
In one embodiment of the invention, the organic molecules comprise or consist of a structure of Formula V:
Formula V
wherein for the substituents any one of the aforementioned definitions applies.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula V-1 , Formula V- 2 and Formula V-3:
Formula V-1 Formula V-2 Formula V-3
wherein for the substituents any one of the aforementioned definitions apply .
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Va-1 , Formula Va-2 and Formula Va-3:
wherein for Rc any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Vb-1 , Formula Vb-2 and Formula Vb-3:
wherein for Rc any one of the aforementioned definitions apply.
In one embodiment of the invention, the organic molecules comprise or consist of a structure of Formula VI:
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula VI-1 , Formula VI-2 and Formula VI-3:
Formula VI-1 Formula VI-2 Formula VI-3
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Vla-1 , Formula Vla-2 and Formula Vla-3:
Formula Vla-1 Formula Vla-2 Formula Vla-3
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Vlb-1 , Formula Vlb-2 and Formula Vlb-3:
Formula Vlb-1 Formula Vlb-2 Formula Vlb-3
wherein for the substituents any one of the aforementioned definitions apply.
In one embodiment of the invention, the organic molecules comprise or consist of a structure of Formula VII:
Formula VII
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula VI 1-1 , Formula VII-2 and Formula VII-3:
Formula VII-1 Formula VII-2 Formula VI 1-3
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Vllla-1 , Formula VII la-2 and Formula VII la-3:
Formula Vlla-1 Formula Vlla-2 Formula Vlla-3
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Vlllb-1 , Formula VII lb-2 and Formula VII lb-3:
Formula Vllb-1 Formula Vllb-2 Formula Vllb-3
wherein for the substituents any one of the aforementioned definitions apply.
In one embodiment of the invention, the organic molecules comprise or consist of a structure of Formula VIII:
Formula VIII
wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula VIII-1 , Formula VIII-2 and Formula VIII-3:
Formula VIII-1 Formula VIII-2 Formula VIII-3 wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Vllla-1 , Formula Vllla-2 and Formula Vllla-3:
Formula Vllla-1 Formula Vllla-2 Formula Vllla-3 wherein for the substituents any one of the aforementioned definitions apply.
In a further embodiment of the invention, the organic molecules comprise or consist of a structure selected from the group of Formula Vlllb-1 , Formula Vlllb-2 and Formula Vlllb-3:
Formula Vlllb-1 Formula Vlllb-2 Formula Vlllb-3
wherein for the substituents any one of the aforementioned definitions apply.
In one embodiment of the invention Rc is at each occurrence independently from another selected from the group consisting of:
Me,
iPr,
lBu,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3 and Ph; and
triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3 and Ph.
As used throughout the present application, the terms "aryl" and "aromatic" may be understood in the broadest sense as any mono-, bi- or polycyclic aromatic moieties. Accordingly, an aryl
group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom. Notwithstanding, throughout the application the number of aromatic ring atoms may be given as subscripted number in the definition of certain substituents. In particular, the heteroaromatic ring includes one to three heteroatoms. Again, the terms“heteroaryl" and“heteroaromatic” may be understood in the broadest sense as any mono-, bi- or polycyclic hetero-aromatic moieties that include at least one heteroatom. The heteroatoms may at each occurrence be the same or different and be individually selected from the group consisting of N, O and S. Accordingly, the term "arylene" refers to a divalent substituent that bears two binding sites to other molecular structures and thereby serving as a linker structure. In case, a group in the exemplary embodiments is defined differently from the definitions given here, for example, the number of aromatic ring atoms or number of heteroatoms differs from the given definition, the definition in the exemplary embodiments is to be applied. According to the invention, a condensed (annulated) aromatic or heteroaromatic polycycle is built of two or more single aromatic or heteroaromatic cycles, which formed the polycycle via a condensation reaction.
In particular, as used throughout the present application the term aryl group or heteroaryl group comprises groups which can be bound via any position of the aromatic or heteroaromatic group, derived from benzene, naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, napthooxazole, anthroxazol, phenanthroxazol, isoxazole, 1 ,2-thiazole, 1 ,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1 ,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1 ,2,3-triazole, 1 ,2,4-triazole, benzotriazole, 1 ,2,3-oxadiazole, 1 ,2,4-oxadiazole, 1 ,2,5-oxadiazole, 1 ,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or combinations of the abovementioned groups.
As used throughout the present application the term cyclic group may be understood in the broadest sense as any mono-, bi- or polycyclic moieties.
As used throughout the present application the term biphenyl as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is defined in regard to the binding site to another chemical moiety.
As used throughout the present application the term alkyl group may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent. In particular, the term alkyl comprises the substituents methyl (Me), ethyl (Et), n-propyl (nPr), i-propyl ('Pr), cyclopropyl, n- butyl (nBu), i-butyl ('Bu), s-butyl (sBu), t-butyl fBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1 -methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1 -methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1 -bicyclo[2,2,2]octyl, 2- bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluorethyl, 1 , 1 -dimethyl-n-hex-1 -yl, 1 ,1 -dimethyl-n-hept-1 -yl, 1 ,1 -dimethyl-n-oct-1 -yl, 1 ,1 -dimethyl-n-dec- 1 -yl, 1 ,1 -dimethyl-n-dodec-1 -yl, 1 ,1 -dimethyl-n-tetradec-1 -yl, 1 ,1 -dimethyl-n-hexadec-1 -yl, 1 , 1 -dimethyl-n-octadec-1 -yl, 1 ,1 -diethyl-n-hex-1 -yl, 1 ,1 -diethyl-n-hept-1 -yl, 1 ,1 -diethyl-n-oct-1 - yl, 1 , 1 -diethyl-n-dec-1 -yl, 1 , 1 -diethyl-n-dodec-1 -yl, 1 , 1 -d iethyl-n-tetradec-1 -yl , 1 , 1 -diethyln-n- hexadec-1 -yl, 1 ,1 -diethyl-n-octadec-1 -yl, 1 -(n-propyl)-cyclohex-l -yl, 1 -(n-butyl)-cyclohex-l -yl, 1 -(n-hexyl)-cyclohex-1 -yl, 1 -(n-octyl)-cyclohex-1 -yl and 1 -(n-decyl)-cyclohex-1 -yl.
As used throughout the present application the term alkenyl comprises linear, branched, and cyclic alkenyl substituents. The term alkenyl group exemplarily comprises the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
As used throughout the present application the term alkynyl comprises linear, branched, and cyclic alkynyl substituents. The term alkynyl group exemplarily comprises ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
As used throughout the present application the term alkoxy comprises linear, branched, and cyclic alkoxy substituents. The term alkoxy group exemplarily comprises methoxy, ethoxy, n- propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.
As used throughout the present application the term thioalkoxy comprises linear, branched, and cyclic thioalkoxy substituents, in which the O of the exemplarily alkoxy groups is replaced by S.
As used throughout the present application, the terms“halogen” and“halo” may be understood in the broadest sense as being preferably fluorine, chlorine, bromine or iodine.
Whenever hydrogen (H) is mentioned herein, it could also be replaced by deuterium at each occurrence.
It is understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. naphtyl, dibenzofuryl) or as if it were the whole molecule (e.g. naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.
In one embodiment, the organic molecules according to the invention have an excited state lifetime of not more than 150 ps, of not more than 100 ps, in particular of not more than 50 ps, more preferably of not more than 10 ps or not more than 7 ps in a film of poly(methyl methacrylate) (PMMA) with 10 % by weight of organic molecule at room temperature.
In one embodiment of the invention, the organic molecules according to the invention represent thermally-activated delayed fluorescence (TADF) emitters, which exhibit a AEST value, which corresponds to the energy difference between the first excited singlet state (S1 ) and the first excited triplet state (T1 ), of less than 5000 cm 1, preferably less than 3000 cm 1, more preferably less than 1500 cm 1, even more preferably less than 1000 cm 1 or even less than 500 cm 1.
In a further embodiment of the invention, the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E (EHOMO(E)) is larger than -6.2 eV, preferably larger than -6.0 eV, more preferably larger than -5.9 eV, even more preferably larger than -5.8 eV, wherein EHOMO(E) is determined by cyclic voltammetry.
In a further embodiment of the invention, the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E (EHOMO(E)) is larger than -5.8 eV, wherein EHOMO(E) is determined by cyclic voltammetry.
In a further embodiment of the invention, the organic molecules according to the invention have an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, with a full width at half maximum of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or
even less than 0.40 eV in a film of poly(methyl methacrylate) (PMMA) with 10 % by weight of organic molecule at room temperature.
In a further embodiment of the invention, the organic molecules according to the invention have a“blue material index” (BMI), calculated by dividing the photoluminescence quantum yield (PLQY) in % by the CIEy color coordinate of the emitted light, of more than 150, in particular more than 200, preferably more than 250, more preferably of more than 300 or even more than 500. The photoluminescence quantum yield determination method applied is described in the experimental section.
Orbital and excited state energies can be determined either by means of experimental methods or by calculations employing quantum-chemical methods, in particular density functional theory calculations. The energy of the highest occupied molecular orbital EHOMO is determined by methods known to the person skilled in the art from cyclic voltammetry measurements with an accuracy of 0.1 eV. The cyclic voltammetry measurement methods are described in the experimental section. The energy of the lowest unoccupied molecular orbital ELUMO is calculated as EHOMO + Egap, wherein Egap is determined as follows: For host compounds, the onset of the emission spectrum of a film with 10 % by weight of host in poly(methyl methacrylate) (PMMA) is used as Egap, unless stated otherwise. For emitter molecules, Egap is determined as the energy at which the excitation and emission spectra of a film with 10% by weight of emitter in PMMA cross.
The energy of the first excited triplet state T 1 is determined from the onset of the emission spectrum at low temperature, typically at 77 K. For host compounds, where the first excited singlet state and the lowest triplet state are energetically separated by > 0.4 eV, the phosphorescence is usually visible in a steady-state spectrum in 2-Me-THF. The triplet energy can thus be determined as the onset of the phosphorescence spectrum. For TADF emitter molecules, the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K, if not otherwise stated measured in a film of PMMA with 10% by weight of emitter. Both for host and emitter compounds, the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum, if not otherwise stated measured in a film of PMMA with 10% by weight of host or emitter compound.
The onset of an emission spectrum is determined by computing the intersection of the tangent to the emission spectrum with the x-axis. The tangent to the emission spectrum is set at the high-energy side of the emission band and at the point at half maximum of the maximum intensity of the emission spectrum.
A further aspect of the invention relates to a process for preparing organic molecules (with an optional subsequent reaction) according to the invention, wherein a R1-, R2-substituted Hal3- fluoropyridine is used as a reactant:
According to the invention, a 1-fluorobenzene EO-2, which is substituted with a coupling group CG2 in 4-position and which is substituted with a coupling group CG3 in 3-position, is used as a reactant, which is reacted with the heterocycle E0-1 , which is substituted with a coupling group Hal3 (reactant E0-1 ). The coupling groups Hal3 and CG2 are chosen as a reaction pair to introduce the heterocycle of EO-2 at the position of CG2. Accordingly, coupling groups CG3 and CG4 are chosen as reaction pair for introducing the heterocycle E0-4 at the position of CG3. Preferably, a so-called Suzuki coupling reaction is used. Here, CG2 is a boronic acid group or a boronic acid ester group, in particular a boronic acid pinacol ester group, and Hal3 is chosen from Cl, Br or I. Analogously, either CG3 is chosen from Cl, Br or I, and CG4 is a
boronic acid group or a boronic acid ester group, in particular a boronic acid pinacol ester group, or CG3 is a boronic acid group or a boronic acid ester group, in particular a boronic acid pinacol ester group, and CG4 is chosen from Cl, Br or I.
An alternative synthesis route comprises the introduction of a nitrogen heterocycle via copper- or palladium-catalyzed coupling to an aryl halide or aryl pseudohalide, preferably an aryl bromide, an aryl iodide, aryl triflate or an aryl tosylate.
Typically, Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(O)) is used as a Pd catalyst, but alternatives are known in the art. For example, the ligand may be selected from the group consisting of S-Phos ([2-dicyclohexylphoshino-2’,6’-dimethoxy-1 ,1’-biphenyl]), X-Phos (2- (dicyclohexylphosphino)-2”,4”,6”-triisopropylbiphenyl), and P(Cy)3 (tricyclohexylphosphine). The salt is, for example, selected from tribasic potassium phosphate and potassium acetate and the solvent can be a pure solvent, such as toluene or dioxane, or a mixture, such as toluene/dioxane/water or dioxane/toluene. A person of skill in the art can determine which Pd catalyst, ligand, salt and solvent combination will result in high reaction yields.
For the reaction of a nitrogen heterocycle in a nucleophilic aromatic substitution with an aryl halide, preferably an aryl fluoride, typical conditions include the use of a base, such as tribasic potassium phosphate or sodium hydride, for example, in an aprotic polar solvent, such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF), for example.
A further aspect of the invention relates to the use of an organic molecule according to the invention as a luminescent emitter or as an absorber, and/or as host material and/or as electron transport material, and/or as hole injection material, and/or as hole blocking material in an optoelectronic device, in particular as a luminescent emitter.
The optoelectronic device may be understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or nearest ultraviolet (UV) range, i.e. , in the range of a wavelength of from 380 to 800 nm. More preferably, the optoelectronic device may be able to emit light in the visible range, i.e., of from 400 to 800 nm.
In the context of such use, the optoelectronic device is more particularly selected from the group consisting of:
• organic light-emitting diodes (OLEDs),
• light-emitting electrochemical cells,
• OLED sensors, especially in gas and vapor sensors not hermetically externally shielded,
• organic diodes,
• organic solar cells,
• organic transistors,
• organic field-effect transistors,
• organic lasers, and
• down-conversion elements.
In a preferred embodiment in the context of such use, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
In the case of the use, the fraction of the organic molecule according to the invention in the emission layer in an optoelectronic device, more particularly in OLEDs, is 1 % to 99 % by weight, more particularly 5 % to 80 % by weight. In an alternative embodiment, the proportion of the organic molecule in the emission layer is 100 % by weight.
In one embodiment, the light-emitting layer comprises not only the organic molecules according to the invention but also a host material whose triplet (T1 ) and singlet (S1 ) energy levels are energetically higher than the triplet (T 1 ) and singlet (S1 ) energy levels of the organic molecule.
A further aspect of the invention relates to a composition comprising or consisting of:
(a) at least one organic molecule according to the invention, in particular in the form of an emitter and/or a host, and
(b) one or more emitter and/or host materials, which differ from the organic molecule according to the invention and
(c) optional one or more dyes and/or one or more solvents.
In one embodiment, the light-emitting layer EML comprises or consists of a composition comprising or consisting of:
(a) at least one organic molecule according to the invention, in particular in the form of an emitter and/or a host, and
(b) one or more emitter and/or host materials, which differ from the organic molecule according to the invention and
(c) optional one or more dyes and/or one or more solvents.
Particularly preferably the light-emitting layer EML comprises or) consists of a composition comprising or consisting of:
(i) 1-50 % by weight, preferably 5-40 % by weight, in particular 10-30 % by weight, of one or more organic molecules according to the invention E;
(ii) 5-99 % by weight, preferably 30-94.9 % by weight, in particular 40-89% by weight, of at least one host compound H; and
(iii) optionally 0-94 % by weight, preferably 0.1-65 % by weight, in particular 1-50 % by weight, of at least one further host compound D with a structure differing from the structure of the molecules according to the invention; and
(iv) optionally 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent; and
(v) optionally 0-30 % by weight, in particular 0-20 % by weight, preferably 0-5 % by weight, of at least one further emitter molecule F with a structure differing from the structure of the molecules according to the invention.
Preferably, energy can be transferred from the host compound H to the one or more organic molecules according to the invention E, in particular transferred from the first excited triplet state T1 (H) of the host compound H to the first excited triplet state T1 (E) of the one or more organic molecules according to the invention E and/ orfrom the first excited singlet state S1 (H) of the host compound H to the first excited singlet state S1 (E) of the one or more organic molecules according to the invention E.
In a further embodiment, the light-emitting layer EML comprises or (essentially) consists of a composition comprising or consisting of:
(i) 1-50 % by weight, preferably 5-40 % by weight, in particular 10-30 % by weight, of one organic molecule according to the invention E;
(ii) 5-99 % by weight, preferably 30-94.9 % by weight, in particular 40-89% by weight, of one host compound H; and
(iii) optionally, 0-94 % by weight, preferably 0.1-65 % by weight, in particular 1-50 % by weight, of at least one further host compound D with a structure differing from the structure of the molecules according to the invention; and
(iv) optionally, 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent; and
(v) optionally, 0-30 % by weight, in particular 0-20 % by weight, preferably 0-5 % by weight, of at least one further emitter molecule F with a structure differing from the structure of the molecules according to the invention.
In one embodiment, the host compound H has a highest occupied molecular orbital HOMO(H) having an energy EHOMO(H) in the range of from -5 to -6.5 eV and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy EHOMO(D), wherein EHOMO(H) > EHOMO(D).
In a further embodiment, the host compound H has a lowest unoccupied molecular orbital LUMO(H) having an energy ELUMO(H) and the at least one further host compound D has a lowest unoccupied molecular orbital LUMO(D) having an energy ELUMO(D), wherein ELUMO(H)
In one embodiment, the host compound H has a highest occupied molecular orbital HOMO(H) having an energy EHOMO(H) and a lowest unoccupied molecular orbital LUMO(H) having an energy ELUMO(H), and
the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy EHOMO(D) and a lowest unoccupied molecular orbital LUMO(D) having an energy ELUMO(D),
the organic molecule according to the invention E has a highest occupied molecular orbital HOMO(E) having an energy EHOMO(E) and a lowest unoccupied molecular orbital LUMO(E) having an energy ELUMO(E),
wherein
EHOMO |_| > ^HOMO ^ and the difference between the energy level of the highest occupied molecular orbital HOMO(E) of the organic molecule according to the invention E (EHOMO(E)) and the energy level of the highest occupied molecular orbital HOMO(H) of the host compound H (EHOMO(H)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV or even between -0.1 eV and 0.1 eV; and ELUMO |_| > ^LUMO ^ and the difference between the energy level of the lowest unoccupied molecular orbital LUMO(E) of the organic molecule according to the invention E (ELUMO(E)) and the lowest unoccupied molecular orbital LUMO(D) of the at least one further host compound D (ELUMO(D)) is between -0.5 eV and 0.5 eV, more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV or even between -0.1 eV and 0.1 eV.
In a further aspect, the invention relates to an optoelectronic device comprising an organic molecule or a composition of the type described here, more particularly in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor, more particularly gas and vapour sensors not hermetically
externally shielded, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.
In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
In one embodiment of the optoelectronic device of the invention, the organic molecule according to the invention E is used as emission material in a light-emitting layer EML.
In one embodiment of the optoelectronic device of the invention the light-emitting layer EML consists of the composition according to the invention described here.
For example, when the optoelectronic device is an OLED, it may exhibit the following layer structure:
1 . substrate
2. anode layer A
3. hole injection layer, HIL
4. hole transport layer, HTL
5. electron blocking layer, EBL
6. emitting layer, EML
7. hole blocking layer, HBL
8. electron transport layer, ETL
9. electron injection layer, EIL
10. cathode layer, wherein the OLED comprises each layer only optionally, except for the EML, which is mandatory. In some embodiments, different layers may be merged and the OLED may comprise more than one layer of each layer type as defined above.
Furthermore, the optoelectronic device may optionally comprise one or more protective layers protecting the device from damaging exposure to harmful species in the environment including, exemplarily moisture, vapor and/or gases.
In one embodiment of the invention, the optoelectronic device is an OLED, which exhibits the following inverted layer structure:
1 . substrate
2. cathode layer
3. electron injection layer, EIL
4. electron transport layer, ETL
5. hole blocking layer, HBL
6. emitting layer, B
7. electron blocking layer, EBL
8. hole transport layer, HTL
9. hole injection layer, HIL
10. anode layer A wherein the OLED with an inverted layer structure comprises each layer other than the emitting layer B only optionally. In some embodiments, different layers may be merged and the OLED may comprise more than one layer of each layer types defined above.
In one embodiment of the invention, the optoelectronic device is an OLED, which may exhibit stacked architecture. In this architecture, contrary to the typical arrangement, where the OLEDs are placed side by side, the individual units are stacked on top of each other. Blended light may be generated with OLEDs exhibiting a stacked architecture, in particular white light may be generated by stacking blue, green and red OLEDs. Furthermore, the OLED exhibiting a stacked architecture may optionally comprise a charge generation layer (CGL), which is typically located between two OLED subunits and typically consists of a n-doped and p-doped layer with the n-doped layer of one CGL being typically located closer to the anode layer.
In one embodiment of the invention, the optoelectronic device is an OLED, which comprises two or more emission layers between anode and cathode. In particular, this so-called tandem OLED comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light and one emission layer emits blue light, and optionally may comprise further layers such as charge generation layers, blocking or transporting layers between the individual emission layers. In a further embodiment, the emission layers are adjacently stacked. In a further embodiment, the tandem OLED comprises a charge generation layer between each two emission layers. In addition, adjacent emission layers or emission layers separated by a charge generation layer may be merged.
The substrate may be formed by any material or composition of materials. Most frequently, glass slides are used as substrates. Alternatively, thin metal layers (e.g., copper, gold, silver or aluminum films) or plastic films or slides may be used. This may allow a higher degree of flexibility. The anode layer A is mostly composed of materials allowing to obtain an (essentially)
transparent film. As at least one of both electrodes should be (essentially) transparent in order to allow light emission from the OLED, either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A comprises a large content or even consists of transparent conductive oxides (TCOs). Such anode layer A may exemplarily comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, wolfram oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or doped polythiophene.
Particularly preferably, the anode layer A (essentially) consists of indium tin oxide (ITO) (e.g., (ln03)0.9(Sn02)0.1 ). The roughness of the anode layer A caused by the transparent conductive oxides (TCOs) may be compensated by using a hole injection layer (HIL). Further, the HIL may facilitate the injection of quasi charge carriers (i.e., holes) in that the transport of the quasi charge carriers from the TCO to the hole transport layer (HTL) is facilitated. The hole injection layer (HIL) may comprise poly-3, 4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS), M0O2, V2O5, CuPC or Cul, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) may also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL). The HIL may exemplarily comprise PEDOT:PSS (poly-3, 4- ethylendioxy thiophene: polystyrene sulfonate), PEDOT (poly-3, 4-ethylendioxy thiophene), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2, 2', 7,7'- tetrakis(n,n-diphenylamino)-9,9’-spirobifluorene), DNTPD (N 1 ,NT-(biphenyl-4,4'-diyl)bis(N1 - phenyl-N4,N4-di-m-tolylbenzene-1 ,4-diamine), NPB (N,N'-nis-(1 -naphthalenyl)-N,N'-bis- phenyl-(1 ,T-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl- amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1 ,4, 5, 8, 9,1 1 -hexaazatriphenylen-hexacarbonitrile) and/or Spiro-NPD (N,N'-diphenyl-N,N'-bis- (1 -naphthyl)-9,9'-spirobifluorene-2, 7-diamine).
Adjacent to the anode layer A or hole injection layer (HIL) typically a hole transport layer (HTL) is located. Herein, any hole transport compound may be used. Exemplarily, electron-rich heteroaromatic compounds such as triarylamines and/or carbazoles may be used as hole transport compound. The HTL may decrease the energy barrier between the anode layer A and the light-emitting layer EML. The hole transport layer (HTL) may also be an electron blocking layer (EBL). Preferably, hole transport compounds bear comparably high energy levels of their triplet states T 1. Exemplarily the hole transport layer (HTL) may comprise a star- shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4- butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4 - cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA (4,4',4"-tris[2- naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-
CN and/or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). In addition, the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may exemplarily be used as inorganic dopant. Tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(l)pFBz) or transition metal complexes may exemplarily be used as organic dopant.
The EBL may exemplarily comprise mCP (1 ,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-Butylphenyl)-3,6- bis(triphenylsilyl)-9H-carbazole), and/or DCB (N,N'-dicarbazolyl-1 ,4-dimethylbenzene).
Adjacent to the hole transport layer (HTL), typically, the light-emitting layer EML is located. The light-emitting layer EML comprises at least one light emitting molecule. Particularly, the EML comprises at least one light emitting molecule according to the invention E. In one embodiment, the light-emitting layer comprises only the organic molecules according to the invention E. Typically, the EML additionally comprises one or more host materials H. Exemplarily, the host material H is selected from CBP (4,4'-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, SiMCP (3,5-Di(9H-carbazol-9- yl)phenyl]triphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2- (diphenylphosphino)phenyl] ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H- carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1 ,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1 ,3,5- triazine) and/or TST (2, 4, 6-tris(9,9'-spirobifluorene-2-yl)-1 ,3,5-triazine). The host material H typically should be selected to exhibit first triplet (T 1 ) and first singlet (S1 ) energy levels, which are energetically higher than the first triplet (T1 ) and first singlet (S1 ) energy levels of the organic molecule.
In one embodiment of the invention, the EML comprises a so-called mixed-host system with at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises exactly one light emitting molecule according to the invention E and a mixed-host system comprising T2T as electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]- 9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2- dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H- carbazole as hole-dominant host. In a further embodiment the EML comprises 50-80 % by weight, preferably 60-75 % by weight of a host selected from CBP, mCP, mCBP, 9-[3-
(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45 % by weight, preferably 15-30 % by weight of T2T and 5-40 % by weight, preferably 10-30 % by weight of light emitting molecule according to the invention.
Adjacent to the light-emitting layer EML an electron transport layer (ETL) may be located. Herein, any electron transporter may be used. Exemplarily, electron-poor compounds such as, e.g., benzimidazoles, pyridines, triazoles, oxadiazoles (e.g., 1 ,3,4-oxadiazole), phosphinoxides and sulfone, may be used. An electron transporter may also be a star-shaped heterocycle such as 1 , 3, 5-tri(1 -phenyl-1 H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may comprise NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1 ,10-phenanthroline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSP01 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(2,2'-bipyridin-5-yl)triphenyle), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1 ,3-bis[3,5-di(pyridin-3- yl)phenyl]benzene) and/or BTB (4,4 -bis-[2-(4,6-diphenyl-1 ,3,5-triazinyl)]-1 ,1 '-biphenyl). Optionally, the ETL may be doped with materials such as Liq. The electron transport layer (ETL) may also block holes or a holeblocking layer (HBL) is introduced.
The HBL may, for example, comprise BCP (2,9-dimethyl-4,7-diphenyl-1 ,10-phenanthroline = Bathocuproine), BAIq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1 ,10-phenanthroline), Alq3 (Aluminum-tris(8- hydroxyquinoline)), TSP01 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T (2,4,6- tris(biphenyl-3-yl)-1 ,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1 ,3,5-triazine), TST (2,4,6- tris(9,9'-spirobifluorene-2-yl)-1 ,3,5-triazine), and/or TCB/TCP (1 ,3,5-tris(N-carbazolyl)benzol/ 1 ,3,5-tris(carbazol)-9-yl) benzene).
Adjacent to the electron transport layer (ETL), a cathode layer C may be located. Exemplarily, the cathode layer C may comprise or may consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also consist of (essentially) non-transparent metals such as Mg, Ca or Al. Alternatively or additionally, the cathode layer C may also comprise graphite and or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also consist of nanoscalic silver wires.
An OLED may further, optionally, comprise a protection layer between the electron transport layer (ETL) and the cathode layer C (which may be designated as electron injection layer (EIL)). This layer may comprise lithium fluoride, cesium fluoride, silver, Liq (8- hydroxyquinolinolatolithium), LhO, BaF2, MgO and/or NaF.
Optionally, also the electron transport layer (ETL) and/or a hole blocking layer (HBL) may comprise one or more host compounds H.
In order to modify the emission spectrum and/or the absorption spectrum of the light-emitting layer EML further, the light-emitting layer EML may further comprise one or more further emitter molecules F. Such an emitter molecule F may be any emitter molecule known in the art. Preferably such an emitter molecule F is a molecule with a structure differing from the structure of the molecules according to the invention E. The emitter molecule F may optionally be a TADF emitter. Alternatively, the emitter molecule F may optionally be a fluorescent and/or phosphorescent emitter molecule which is able to shift the emission spectrum and/or the absorption spectrum of the light-emitting layer EML. Exemplarily, the triplet and/or singlet excitons may be transferred from the emitter molecule according to the invention E to the emitter molecule F before relaxing to the ground state SO by emitting light typically red-shifted in comparison to the light emitted by emitter molecule E. Optionally, the emitter molecule F may also provoke two-photon effects (i.e., the absorption of two photons of half the energy of the absorption maximum).
Optionally, an optoelectronic device (e.g., an OLED) may exemplarily be an essentially white optoelectronic device. Exemplarily such white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and/or red light. Then, there may also optionally be energy transmittance between two or more molecules as described above.
As used herein, if not defined more specifically in the particular context, the designation of the colors of emitted and/or absorbed light is as follows: violet: wavelength range of >380-420 nm;
deep blue: wavelength range of >420-480 nm;
sky blue: wavelength range of >480-500 nm;
green: wavelength range of >500-560 nm;
yellow: wavelength range of >560-580 nm;
orange: wavelength range of >580-620 nm;
red: wavelength range of >620-800 nm.
With respect to emitter molecules, such colors refer to the emission maximum. Therefore, exemplarily, a deep blue emitter has an emission maximum in the range of from >420 to
480 nm, a sky blue emitter has an emission maximum in the range of from >480 to 500 nm, a green emitter has an emission maximum in a range of from >500 to 560 nm, a red emitter has an emission maximum in a range of from >620 to 800 nm.
A deep blue emitter may preferably have an emission maximum of below 480 nm, more preferably below 470 nm, even more preferably below 465 nm or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm or even above 450 nm.
Accordingly, a further aspect of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m2 of more than 8 %, more preferably of more than 10 %, more preferably of more than 13 %, even more preferably of more than 15 % or even more than 20 % and/or exhibits an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm and/or exhibits a LT80 value at 500 cd/m2 of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h or even more than 1000 h. Accordingly, a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20 or even more preferably less than 0.15 or even less than 0.10.
A further aspect of the present invention relates to an OLED, which emits light at a distinct color point. According to the present invention, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the invention emits light with a FWHM of the main emission peak of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or even less than 0.40 eV.
A further aspect of the present invention relates to an OLED, which emits light with Cl Ex and CIEy color coordinates close to the CIEx and CIEy color coordinates of the primary color blue (CIEx = 0.131 and CIEy = 0.046) as defined by ITU-R Recommendation BT.2020 (Rec. 2020) and thus is suited for the use in Ultra High Definition (UHD) displays, e.g. UHD-TVs. Accordingly, a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and/ or a a CIEy color coordinate of between 0.00 and 0.45,
preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.
In a further aspect, the invention relates to a method for producing an optoelectronic component. In this case an organic molecule of the invention is used.
The optoelectronic device, in particular the OLED according to the present invention can be produced by any means of vapor deposition and/or liquid processing. Accordingly, at least one layer is
prepared by means of a sublimation process,
prepared by means of an organic vapor phase deposition process,
prepared by means of a carrier gas sublimation process,
solution processed, or
printed.
Another aspect of the present invention relates to a process for producing an optoelectronic device, wherein an organic molecule or composition according to the invention is used, in particular comprising the processing of the organic molecule or of the composition by a vacuum evaporation method or from a solution.
Further steps used to produce the optoelectronic device, in particular the OLED according to the present invention, comprise depositing different layers individually and successively on a suitable substrate by means of subsequent deposition processes. The individual layers may be deposited using the same or differing deposition methods.
Vapor deposition processes exemplarily comprise thermal (co)evaporation, chemical vapor deposition and physical vapor deposition. For active matrix OLED display, an AMOLED backplane is used as substrate. The individual layer may be processed from solutions or dispersions employing adequate solvents. Solution deposition process exemplarily comprise spin coating, dip coating and jet printing. Liquid processing may optionally be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere) and the solvent may optionally be completely or partially removed by means known in the state of the art.
Examples
General synthesis scheme I
3-chloro-4-fluorophenylboronic acid pinacol ester (1.00 equivalents), 2-chloro-4,6-diphenyl- 1 ,3,5-triazine (CAS 3842-55-5; 1.00 equivalents), Tetrakis(triphenylphosphine)palladium(0)
(0.03 equivalents), and potassium carbonate (3.00 equivalents) are stirred under nitrogen atmosphere in a THF/water mixture (ratio of 2:1 ) at 80 °C for 16 h. After cooling down to room temperature (rt), the mixture is filtered through a fiber glass filter, the filter cake successively washed with water and acetone and the filtrate discarded. The residue is collected, dried in vacuo and used without further purification (yield: 92%).
General procedure for synthesis AAV1-2
3-chloro-4-fluorophenylboronic acid (CAS 144432-85-9; 1 .00 equivalents), 4-chloro-2,6- diphenylpyrimidine (CAS 29509-91 -9; 1.00 equivalents), 1 ,1 '-
Bis(diphenylphosphino)ferrocene-palladium(ll) dichloride (CAS 72287-26-4 0.0.02 equivalent), and potassium carbonate (6.00 equivalents) are stirred under nitrogen atmosphere in a tetrahydrofuran dioxane/H20 mixture (ratio of 10:1 ) at 100 °C for 16 h. After cooling down to room temperature (rt), the reaction mixture is poured into water, the product is filtered and washed with ethanol (EtOH).
General procedure for synthesis AAV1-3
The same procedure is used as for AAV1-2 but instead of 4-chloro-2,6-diphenylpyrimidine 2-chloro-2,6-diphenylpyrimidine (CAS 2915-16-4) is used.
EO-31 (1 .00 equivalent), the optionally phenyl substituted phenylboronic acid or phenylboronic acid pinacol ester E0-41 (1 .50 equivalents), Pd2(dba)3 (0.01 equivalents),
2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 0.04 equivalents), and tribasic potassium phosphate (3.00 equivalents) are stirred under nitrogen atmosphere in a toluene/water mixture (ratio: 10:1 ) at 1 10°C overnight. After cooling down to room temperature (rt), the reaction mixture is added dichloromethane and is subsequently filtered through a fiber glass filter sheet. The aqueous layer is removed from the biphasic filtrate, the organic layer is dried over MgS04, filtered and concentrated. The crude is purified either by recrystallization or by flash chromatography (yields: 77 - 99%).
General procedure for synthesis AAV2-2
EO-32 (1 .00 equivalent), bis-(pinacolato)diboron (1 .5 equivalents, CAS 73183-34-3), tris(dibenzylideneacetone)dipalladium(0) Pd2(dba)3 (0.02 equivalents, CAS 51364-51 -3),
X-Phos (0.08 equivalents, CAS 564483-18-7) and potassium acetate (KOAc, 3.0 equivalents) are stirred under nitrogen atmosphere in dry toluene at 1 10 °C for 16 h. After cooling down to room temperature (RT) the reaction mixture is extracted with ethyl acetate/brine. The organic phases are collected, washed with brine and dried over MgS04. The organic solvent is removed, the crude product was washed with cyclohexane and recrystallized from EtOH.
The product E0-32I reacts further with 5'-Bromo-m-terphenyl (CAS: 103068-20-8) (1.00 equivalents), tetrakis(triphenylphosphine)palladium(0) (0.1 equivalent) and potassium carbonate (3.00 equivalents) are stirred under nitrogen atmosphere in a tetrahydrofuran (THF)/water mixture (ratio of 10:1 ) at 75 °C for 16 h. After cooling down to room temperature (rt), the reaction mixture is poured into water, the product is filtered and washed with ethanol (EtOH).
General procedure for synthesis AAV2-3
This same procedure is used as for AAV2-2 but instead of E0-032 EO-33 was used.
General procedure for synthesis AAV3
Z1 , Z2 or Z3 (1.00 equivalent), the corresponding donor molecule D-H (1.00 equivalent) and tribasic potassium phosphate (2.0 equivalents) are suspended under nitrogen atmosphere in DMSO and stirred at 120 °C for 20 h. After cooling down to rt, the reaction mixture is poured into water and the resulting precipitate is filtered off through a fiber glass filter sheet. Subsequently the residue is dissolved in dichloromethane, washed with saturated sodium chloride solution if required, dried over MgS04 and concentrated under reduced pressure. The crude product is purified by recrystallization or by flash chromatography. The product is obtained as a solid.
In particular, the donor molecule D-H is a 3,6-substituted carbazole (e.g., 3,6- dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g., 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1 ,8-substituted carbazole (e.g., 1 ,8-dimethylcarbazole, 1 ,8-diphenylcarbazole, 1 ,8-di-tert- butylcarbazole), a 1 -substituted carbazole (e.g., 1 -methylcarbazole, 1 -phenylcarbazole, 1 -tert- butylcarbazole), a 2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole, 2-tert- butylcarbazole), or a 3-substituted carbazole (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3- tert-butylcarbazole).
Exemplarily a halogen-substituted carbazole, particularly 3-bromocarbazole, can be used as D-H.
In a subsequent reaction, a boronic acid ester functional group or boronic acid functional group may be, for example, introduced at the position of the one or more halogen substituents, which was introduced via D-H, to yield the corresponding carbazol-3-ylboronic acid ester or carbazol- 3-ylboronic acid, e.g., via the reaction with bis(pinacolato)diboron (CAS No. 73183-34-3). Subsequently, one or more substituents Ra may be introduced in place of the boronic acid ester group or the boronic acid group via a coupling reaction with the corresponding halogenated reactant Ra-Hal, preferably Ra-CI and Ra-Br.
Alternatively, one or more substituents Ra may be introduced at the position of the one or more halogen substituents, which was introduced via D-H, via the reaction with a boronic acid of the substituent Ra [Ra-B(OH)2] or a corresponding boronic acid ester.
Cyclic voltammetry
Cyclic voltammograms are measured from solutions having concentration of 10 3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp2/FeCp2+ as internal standard. The HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).
Density functional theory calculation
Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (Rl). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets (and a m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.
Photophysical measurements
Sample pretreatment: Spin-coating
Apparatus: Spin150, SPS euro.
The sample concentration is 1 mg/ml, dissolved in a suitable solvent.
Program: 1 ) 3 s at 400 rpm; 20 s at 1000 rpm at 1000 rpm/s. 3) 10 s at 4000 rpm at 1000 rpm/s. After coating, the films are tried at 70 °C for 1 min.
Photoluminescence spectroscopy and TCSPC ( Time-correlated single-photon counting) Steady-state emission spectroscopy is measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.
Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Y von TCSPC hub.
Excitation sources:
NanoLED 370 (wavelength: 371 nm, puls duration: 1 ,1 ns)
NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)
SpectraLED 310 (wavelength: 314 nm)
SpectraLED 355 (wavelength: 355 nm).
Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.
Time-resolved PL spectrospcopy in the ps-range
Time-resolved PL measurements were performed on a FS5 fluorescence spectrometer from Edinburgh Instruments. Compared to measurements on the HORIBA setup, better light gathering allows for an optimized signal to noise ratio, which favors the FS5 system especially for transient PL measurements of delayed fluorescence characteristics. The FS5 consists of a xenon lamp providing a broad spectrum. The continuous light source is a 150W xenon arc lamp, selected wavelengths are chosen by a Czerny-Turner monochromator, which is also used to set specific emission wavelengths. The sample emission is directed towards a sensitive R928P photomultiplier tube (PMT), allowing the detection of single photons with a peak quantum efficiency of up to 25 % in the spectral range between 200 nm to 870 nm. The detector is a temperature stabilized PMT, providing dark counts below 300 cps (counts per second). Finally, to determine the transient decay lifetime of the delayed fluorescence, a tail fit using three exponential functions is applied. By weighting the specific lifetimes t* with their corresponding amplitudes Ai
the delayed fluorescence lifetime TDF is determined.
Photoluminescence quantum yield measurements
For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system ( Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0.
Emission maxima are given in nm, quantum yields F in % and CIE coordinates as x,y values. PLQY is determined using the following protocol:
1 ) Quality assurance: Anthracene in ethanol (known concentration) is used as reference
2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength
3) Measurement
Quantum yields are measured for sample of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:
wherein nPhoton denotes the photon count and Int. the intensity.
Production and characterization of optoelectronic devices
OLED devices comprising organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight- percentage of one or more compounds is given in %. The total weight-percentage values amount to 100 %, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100 %.
The not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current. The OLED device lifetime is extracted from the change of the luminance during operation at constant current density. The LT50 value corresponds to the time, where the measured luminance decreased to 50 % of the initial luminance, analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80 % of the initial luminance, LT 95 to the time point, at which the measured luminance decreased to 95 % of the initial luminance etc.
Accelerated lifetime measurements are performed (e.g. applying increased current densities). Exemplarily LT80 values at 500 cd/m2 are determined using the following equation:
wherein Lo denotes the initial luminance at the applied current density.
The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.
HPLC-MS
HPLC-MS analysis is performed on an HPLC by Agilent (1 100 series) with MS-detector (Thermo LTQ XL).
Exemplary a typical HPLC method is as follows: a reverse phase column 4,6mm x 150mm, particle size 3,5 pm from Agilent (ZORBAX Eclipse Plus 95A C18, 4.6 x 150 mm, 3.5 pm HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) following gradients
Flow rate [ml/min] time [min] A[%] B[%] C[%]
2.5 0 40 50 10
2.5 5 40 50 10
2.5 25 10 20 70
2.5 35 10 20 70
2.5 35.01 40 50 10
2.5 40.01 40 50 10
2.5 41.01 40 50 10 using the following solvent mixtures:
An injection volume of 5 pL from a solution with a concentration of 0.5 mg/mL of the analyte is taken for the measurements.
Ionization of the probe is performed using an APCI (atmospheric pressure chemical ionization) source either in positive (APCI +) or negative (APCI -) ionization mode.
Example 1
Example 1 was synthesized according to
AAV1-1 (yield 92%),
AAV2-1 (yield 99%), wherein 2-biphenylboronic acid (CAS 4688-76-0) was used as reactant E0-41 , and
AAV3 (yield 87%).
Figure 1 depicts the emission spectrum of Example 1 (10 % by weight in PMMA). The emission maximum (Amax) is at 462 nm. The photoluminescence quantum yield (PLQY) is 77 %, the full width at half maximum (FWHM) is 0.41 eV. The resulting CIEX coordinate is determined at 0.15 and the CIEy coordinate at 0.17. The HOMO(E) is -5.87 eV.
Example 2
Example 2 was synthesized according to
AAV1-1 (yield 92%),
AAV2-1 (yield 99%), wherein 2-biphenylboronic acid (CAS 4688-76-0) was used as reactant EO-41 , and
AAV3 (yield 68%).
Figure 2 depicts the emission spectrum of Example 2 (10 % by weight in PMMA). The emission maximum (Amax) is at 453 nm. The photoluminescence quantum yield (PLQY) is 76 %, the full width at half maximum (FWHM) is 0.43 eV. The resulting CIEX coordinate is determined at 0.15 and the CIEy coordinate at 0.14 and HOMO(E) is -5.89 eV.
Example 3
Example 3 was synthesized according to
AAV1-1 (yield 92%),
AAV2-1 (yield 77%), wherein biphenyl-3-boronic acid (CAS 5122-95-2) was used as reactant E0-41 , and
AAV3 (yield 64%).
HPLC-LCMS:
Figure 3 depicts the emission spectrum of Example 3 (10 % by weight in PMMA). The emission maximum (Amax) is at 454 nm. The photoluminescence quantum yield (PLQY) is 68 %, the full width at half maximum (FWHM) is 0.43 eV. The resulting CIEX coordinate is determined at 0.15 and the CIEy coordinate at 0.15. The energy level of the highest occupied molecular orbital HOMO(E) is -5.93 eV.
Example 4
Example 3 was synthesized according to
AAV1-2 (yield 98 %),
AAV2-2 (yield 91 %), wherein 5’-bromo-m-terphenyl (CAS 103068-20-8) was used as reactant E0-42d, and
AAV3 (yield 87 %).
HPLC-LCMS:
Figure 4 depicts the emission spectrum of Example 4 (10 % by weight in PMMA). The emission maximum (Amax) is at 444 nm. The photoluminescence quantum yield (PLQY) is 55 %, the full width at half maximum (FWHM) is 0.45 eV. The resulting CIEX coordinate is determined at 0.15 and the CIEy coordinate at 0.12.
Example 5
Example 5 was synthesized according to
AAV1-3 (yield 54 %),
AAV2-3 (yield 84 %), wherein 5’-bromo-m-terphenyl (CAS 103068-20-8) was used as reactant EO-42, and
AAV3 (yield 98 %).
HPLC-LCMS:
Figure 5 depicts the emission spectrum of Example 5 (10 % by weight in PMMA). The emission maximum (Amax) is at 427 nm. The photoluminescence quantum yield (PLQY) is 32 %, the full width at half maximum (FWHM) is 0.46 eV. The resulting CIEX coordinate is determined at 0.16 and the CIEy coordinate at 0.08.
Example 6
Example 6 was synthesized according to
AAV1-1 (yield 92%),
AAV2-1 (yield 77%), wherein biphenyl-3-boronic acid (CAS 5122-95-2) was used as reactant
E0-41 , and
AAV3 (yield 7.8%), wherein 3-[(3-trimethylsilyl)phenyl]-9/-/-carbazole was used as compound
D-H.
Figure 6 depicts the emission spectrum of Example 6 (10 % by weight in PMMA). The emission maximum (Amax) is at 444 nm. The photoluminescence quantum yield (PLQY) is 66 %, the full width at half maximum (FWHM) is 0.44 eV. The resulting CIEX coordinate is determined at 0.15 and the CIEy coordinate at 0.1 1 . The energy level of the highest occupied molecular orbital HOMO(E) is -5.85 eV.
Example 7
Example 7 was synthesized according to
AAV1-1 (yield 92%),
AAV2-1 (yield 99%), wherein biphenyl-3-boronic acid (CAS 5122-95-2) was used as reactant E0-41 , and
AAV3 (yield 68%).
Figure 7 depicts the emission spectrum of Example 7 (10 % by weight in PMMA). The emission maximum (Amax) is at 453 nm. The photoluminescence quantum yield (PLQY) is 76 %, the full width at half maximum (FWHM) is 0.43 eV. The resulting CIEX coordinate is determined at 0.15 and the CIEy coordinate at 0.14. The energy level of the highest occupied molecular orbital HOMO(E) is -5.89 eV.
Additional Examples of Organic Molecules of the Invention
The drawings of the figures show:
Figure 1 Emission spectrum of Example 1 (10% by weight) in PMMA.
Figure 2 Emission spectrum of Example 2 (10% by weight) in PMMA.
Figure 3 Emission spectrum of Example 3 (10% by weight) in PMMA.
Figure 4 Emission spectrum of Example 4 (10% by weight) in PMMA.
Figure 5 Emission spectrum of Example 5 (10% by weight) in PMMA.
Figure 6 Emission spectrum of Example 6 (10% by weight) in PMMA.
Figure 7 Emission spectrum of Example 7 (10% by weight) in PMMA.
Claims
1. Organic molecule, comprising a structure of Formula I,
Formula I
wherein
Q is selected from the group consisting of N and C-RPy;
T, V, W, X, Y is independently from each other selected from the group consisting of R1 and phenyl, which is optionally substituted with one or more substituents R2;
RTz is at each occurrence independently from another selected from the group consisting of hydrogen,
deuterium,
Ci-C5-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
Ce-Cis-aryl,
which is optionally substituted with one or more substituents R5; and
C3-Ci7-heteroaryl,
which is optionally substituted with one or more substituents R5;
RPy is at each occurrence independently from another selected from the group consisting of hydrogen,
deuterium,
Ci-Cs-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
Ce-Cis-aryl,
which is optionally substituted with one or more substituents R6; and
C3-Ci7-heteroaryl,
which is optionally substituted with one or more substituents R6;
R1 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium,
Ci-Cs-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and Ce-Cis-aryl,
which is optionally substituted with one or more substituents R6;
R2 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium,
Ci-Cs-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-Cs-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and Ce-Cis-aryl,
which is optionally substituted with one or more substituents R6;
Z is at each occurrence independently from another selected from the group consisting of: a direct bond, CR3R4, C=CR3R4, C=0, C=NR3, NR3, O, SiR3R4, S, S(O) and S(0)2;
Ra, R3 and R4 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, OSO2R5, CF3, CN, F, Br, I, Ci-C4o-alkyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CFh-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-alkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CFh-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-thioalkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CFh-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkenyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CFh-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkynyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CFh-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ce-Ceo-aryl,
which is optionally substituted with one or more substituents R5;
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring- closure with one or more of the other substituents selected from the group consisting of Ra, R3, R4 and R5;
R5 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R6)2, OR6, Si(R6)3, B(OR6)2, OSO2R6, CF3, CN, F, Br, I,
Ci-C4o-alkyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
Ci-C4o-alkoxy,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
Ci-C4o-thioalkoxy,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
C2-C4o-alkenyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
C2-C4o-alkynyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C=CR6, CºC, Si(R6)2, Ge(R6)2, Sn(R6)2, C=0, C=S, C=Se, C=NR6, P(=0)(R6), SO, S02, NR6, O, S or CONR6;
Ce-Ceo-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R6; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring- closure with one or more of the other substituents selected from the group consisting of Ra, R3, R4 and R5;
R6 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, CF3, CN, F,
Ci-C5-alkyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
Ci-Cs-alkoxy,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
Ci-Cs-thioalkoxy,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
Ce-Cis-aryl,
which is optionally substituted with one or more C-i-Cs-alkyl substituents;
C3-Ci7-heteroaryl,
which is optionally substituted with one or more C-i-Cs-alkyl substituents;
N(C6-Ci8-aryl)2;
N(C3-Ci7-heteroaryl)2,
and N(C3-Ci7-heteroaryl)(C6-Ci8-aryl); wherein optionally, the substituents Ra, R3, R4 or R5 independently from each other form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents of the other substituents Ra, R3, R4 or R5; wherein the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system contains at least one atom selected from the group consisting of N, S and O; wherein the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system is optionally substituted with at least one substituent R5, and
optionally forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system together with one or more of the other Ra, R3, R4 or R5 within the organic molecule; wherein the mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system is optionally substituted with at least one substituent R6; wherein
at least one ring member Q is N;
at least one substituent selected from the group consisting of T, V, W, X and Y is phenyl which is optionally substituted with one or more substituents R2, and
if exactly one substituent selected from the group consisting of T and Y is phenyl, W is hydrogen.
2. Organic molecule according to claim 1 , wherein the first chemical moiety comprises a structure of Formula lla:
Formula lla
wherein
Y* and W# is H,
T#, V#, and X# is independently from each other selected from the group consisting of H and phenyl, which is optionally substituted with one or more substituents R2;
wherein
at least one substituent selected from the group consisting of T#, V#, and X# is phenyl which is optionally substituted with one or more substituents R2.
3. Organic molecule according to claim 1 or 2, wherein RTz is phenyl, which is optionally substituted with one or more substituents R5.
4. Organic molecule according to one or more of claims 1 to 3, wherein R1, R2 and RPy is H at each occurrence.
5. Organic molecule according to one or more of claims 1 to 4, comprising a structure of Formula lla:
Formula llaa
wherein
W# and Y# is H,
T#, V#, and X# is independently from each other selected from the group consisting of H and phenyl, which is optionally substituted with one or more substituents R2;
Wherein at least one substituent selected from the group consisting of T#, V#, and X# is phenyl which is optionally substituted with one or more substituents R2.
6. Organic molecule according to one or more of claims 1 to 5, comprising a structure of Formula lib:
Formula lib wherein
Rb is at each occurrence independently from another selected from the group consisting of: deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, 0S02R5, CF3, CN, F, Br, I,
Ci-C4o-alkyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-alkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-thioalkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkenyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkynyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ce-Ceo-aryl,
which is optionally substituted with one or more substituents R5; and
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5.
7. Organic molecule according to one or more of claims 1 to 5, comprising a structure of Formula lie:
Formula lie wherein
Rb is at each occurrence independently from another selected from the group consisting of deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, 0S02R5, CF3, CN, F, Br, I,
Ci-C4o-alkyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-alkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ci-C4o-thioalkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkenyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
C2-C4o-alkynyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C=CR5, CºC, Si(R5)2, Ge(R5)2, Sn(R5)2, C=0, C=S, C=Se, C=NR5, P(=0)(R5), SO, S02, NR5, O, S or CONR5;
Ce-Ceo-aryl,
which is optionally substituted with one or more substituents R5; and
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5.
8. Organic molecule according to claim 6 or 7, wherein Rb is at each occurrence independently from another selected from the group consisting of:
Me, 'Pr, lBu, CN, CF3,
Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3 and Ph;
pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3 and Ph;
pyrimidyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3 and Ph;
carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3 and Ph;
triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, 'Pr, lBu, CN, CF3, and Ph;
and
N(Ph)2.
9. Use of an organic molecule according to one or more of claims 1 to 8 as a luminescent emitter and/or as a host material and/or as an electron transport material and/or as a hole injection material and/or as a hole blocking material in an optoelectronic device.
10. Use according to claim 9, wherein the optoelectronic device is selected from the group consisting of:
• organic light-emitting diodes (OLEDs),
• light-emitting electrochemical cells,
• OLED-sensors,
• organic diodes,
• organic solar cells,
• organic transistors,
• organic field-effect transistors,
• organic lasers, and
• down-conversion elements.
1 1 . Composition, comprising:
(a) at least one organic molecule according to one or more of claims 1 to 8, in particular in the form of an emitter and/or a host, and
(b) one or more emitter and/or host materials, which differs from the organic molecule, and
(c) optionally, one or more dyes and/or one or more solvents.
12. Optoelectronic device, comprising an organic molecule according to one or more of claims 1 to 8 or a composition according to claim 1 1 , in particular in form of a device selected from the group consisting of: organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser, and down-conversion element.
13. Optoelectronic device according to claim 12, comprising or consisting of:
- a substrate,
- an anode, and
- a cathode, wherein the anode and/or the cathode are disposed on the substrate, and
- at least a light-emitting layer, which is arranged between the anode and the cathode and which comprises the organic molecule or the composition.
14. Method for producing an optoelectronic device, wherein an organic molecule according to any one of claims 1 to 8 or a composition according to claim 1 1 is used.
15. Method according to claim 14, comprising processing the organic molecule or the composition by a vacuum evaporation method or from a solution.
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EP4198026A1 (en) * | 2021-12-14 | 2023-06-21 | Novaled GmbH | Compounds for use in semiconductiong materials suitable for electronic devices |
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CN113493446A (en) * | 2020-04-03 | 2021-10-12 | 南京高光半导体材料有限公司 | Carbazolyl-based organic electroluminescent compound and organic electroluminescent device |
EP4198026A1 (en) * | 2021-12-14 | 2023-06-21 | Novaled GmbH | Compounds for use in semiconductiong materials suitable for electronic devices |
WO2023110330A1 (en) * | 2021-12-14 | 2023-06-22 | Novaled Gmbh | Compounds for use in semiconductiong materials suitable for electronic devices |
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