WO2015158411A1 - Materialien für elektronische vorrichtungen - Google Patents
Materialien für elektronische vorrichtungen Download PDFInfo
- Publication number
- WO2015158411A1 WO2015158411A1 PCT/EP2015/000603 EP2015000603W WO2015158411A1 WO 2015158411 A1 WO2015158411 A1 WO 2015158411A1 EP 2015000603 W EP2015000603 W EP 2015000603W WO 2015158411 A1 WO2015158411 A1 WO 2015158411A1
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- WO
- WIPO (PCT)
- Prior art keywords
- aromatic ring
- formula
- substituted
- atoms
- groups
- Prior art date
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- 239000000463 material Substances 0.000 title description 39
- 238000000034 method Methods 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims description 145
- 150000001875 compounds Chemical class 0.000 claims description 133
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 230000005525 hole transport Effects 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 239000000412 dendrimer Substances 0.000 claims description 15
- 229920000736 dendritic polymer Polymers 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 11
- IPFDTWHBEBJTLE-UHFFFAOYSA-N 2h-acridin-1-one Chemical class C1=CC=C2C=C3C(=O)CC=CC3=NC2=C1 IPFDTWHBEBJTLE-UHFFFAOYSA-N 0.000 claims description 10
- 239000002019 doping agent Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
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- -1 Dihydropyrenes Chemical compound 0.000 description 30
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- 125000005259 triarylamine group Chemical group 0.000 description 6
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- 230000000875 corresponding effect Effects 0.000 description 5
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- 239000000543 intermediate Substances 0.000 description 5
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- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 101150107979 MS4A3 gene Proteins 0.000 description 4
- 102100032517 Membrane-spanning 4-domains subfamily A member 3 Human genes 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 125000004986 diarylamino group Chemical group 0.000 description 4
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- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
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- 230000007704 transition Effects 0.000 description 3
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- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
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- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
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- 150000001340 alkali metals Chemical class 0.000 description 2
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
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- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
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- 150000001987 diarylethers Chemical class 0.000 description 1
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- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
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- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
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- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- YSZJKUDBYALHQE-UHFFFAOYSA-N rhenium trioxide Chemical compound O=[Re](=O)=O YSZJKUDBYALHQE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 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
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Definitions
- the present application relates to a hetero-spirobifluorene compound of a formula (I) defined in more detail below.
- the compound is preferably used in an electronic device, more preferably in an organic electroluminescent device (OLED).
- OLED organic electroluminescent device
- organic electronic devices are understood as meaning so-called organic electronic devices (organic electronic devices) which use organic semiconductor materials
- OLEDs are called electronic
- Devices understood that have one or more layers containing organic compounds and emit light when applying electrical voltage.
- Electron blocking layers and emitting layers are Electron blocking layers and emitting layers.
- triarylamines As hole transporting materials in the above-mentioned layers. These can represent mono triarylamines, such as
- spiro-bisacridine compounds in OLEDs, for example from JP 2002-265938, is known in the prior art.
- the compounds described in this disclosure either have no substituents on the benzene rings of the spiro-bisacridine backbone, or they have phenyl groups on the nitrogen atoms of the spiro-bisacridine backbone.
- Hole-carrying layers of the electronic devices are continuously being searched for new materials with corresponding properties.
- the compounds found have one or more properties selected from very good hole-conducting properties, very good
- the subject of the present invention is a compound of the formula (I)
- Y is the same or different N or P at each occurrence;
- X is the same or different CR 1 or N at each occurrence;
- Ar 1 , Ar 2 is identical or different at each occurrence, an aromatic ring system having 6 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or a
- Ring atoms which may be substituted by one or more R 2 radicals;
- Ar 3 , Ar 4 , Ar 5 , Ar 6 is the same or different at each occurrence
- aromatic ring system having 6 to 40 aromatic ring atoms, which may be substituted by one or more R 2 radicals, or a heteroaromatic ring system having 5 to 40 aromatic
- Ring atoms which may be substituted by one or more R 2 radicals;
- aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more radicals R 1 and R 2 may be linked together and form a ring; wherein said alkyl, alkoxy, alkenyl and
- Alkynyl groups and said aromatic ring systems and heteroaromatic ring systems may each be substituted with one or more R 3 radicals; and wherein one or more Ch groups in said alkyl, alkoxy, alkenyl and
- R 4 is the same or different on each occurrence selected from H, D, F, CN, alkyl groups having 1 to 20 carbon atoms, aromatic
- Ring atoms wherein two or more R 4 may be linked together and form a ring; and wherein said alkyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted with F or CN; a, b, c, d are the same or different at each occurrence 0 or 1; where at least one of the two groups Ar 1 and Ar 2 is an aromatic ring system having 12 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or a
- heteroaromatic ring system having 12 to 40 aromatic ring atoms which may be substituted with one or more R 2 radicals; and wherein at least one of the indices a, b, c and d is equal to 1.
- aromatic cycle ie benzene, or a fused aromatic polycycle, for example naphthalene, phenanthrene or anthracene, understood.
- a condensed aromatic polycycle consists in the context of the present application of two or more with each other
- a heteroaryl group in the context of this invention contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
- the heteroatoms of the heteroaryl group are preferred
- a heteroaryl group in the sense of this invention is understood as meaning either a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a fused heteroaromatic polycycle, for example quinoline or carbazole.
- a condensed heteroaromatic polycycle consists of two or more simple heteroaromatic rings condensed together. By condensation between cycles it is to be understood that the cycles share at least one edge with each other.
- An aryl or heteroaryl group which may be substituted in each case by the abovementioned radicals and which may be linked via any position on the aromatic or heteroaromatic compounds is understood in particular to mean groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, Dihydropyrenes, chrysene, perylene, triphenylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, Dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline
- An aromatic ring system in the sense of this invention contains 6 to 60 C atoms in the ring system and does not comprise any heteroatoms as aromatic ring atoms. An aromatic ring system in the sense of this invention therefore contains no heteroaryl groups. Under an aromatic ring system
- Ring system in the context of this invention is to be understood as a system which does not necessarily contain only aryl groups, but in which several aryl groups by a single bond or by a non-aromatic moiety, such as one or more optionally substituted C, Si, N, O - or S-atoms, can be connected.
- the non-aromatic unit preferably comprises less than 10% of the atoms other than H, based on the total number of H atoms
- Systems such as 9,9'-spirobifluorene, 9,9'-diaryl fluorene, triarylamine, diaryl ethers and stilbene as aromatic ring systems in the context of this invention are understood, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl , Alkenyl or alkynyl group or by a silyl group. Furthermore, systems in which two or more aryl groups over
- Ringsystems understood in the context of this invention, such as systems such as biphenyl and terphenyl.
- a heteroaromatic ring system in the context of this invention contains 5 to 60 aromatic ring atoms, of which at least one
- Ring systems are preferably selected from N, O and / or S.
- a heteroaromatic ring system corresponds to the abovementioned definition of an aromatic ring system, but has at least one heteroatom as one of the aromatic ring atoms. It differs from an aromatic ring system as defined by the
- Heteroatom may contain as aromatic ring atom.
- Ring atoms or a heteroaromatic ring system having 5 to 60 aromatic ring atoms are understood in particular groups which are derived from the groups mentioned above under aryl groups and heteroaryl groups and of biphenyl, terphenyl, quaterphenyl,
- Fluorene Fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene,
- alkoxy or thioalkyl group having 1 to 40 carbon atoms in which also single H atoms or CH 2 groups by the above in the Definition of the groups mentioned may be substituted, are preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2 Methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n -propylthio, i -propylthio, n Butylthio, i-but
- the two radicals are linked together by a chemical bond, under the formulation that two or more radicals can form a ring with one another.
- the second radical forms a ring to the position to which the hydrogen atom
- the compound of the formula (I) does not comprise an arylamino group as a substituent.
- Arylamino group is understood in the context of the present application a group in which one or more aryl or heteroaryl groups, preferably three aryl or heteroaryl groups, bind to a nitrogen atom.
- the compound of formula (I) does not comprise a fused aryl group having more than 10 aromatic ring atoms and no fused one
- indices selected from the indices a, b, c and d are preferably 1, more preferably exactly 1 or 2 indices selected from the indices a, b, c and d are equal to 1.
- the subscript a is equal to 1 and the subscripts b, c and d are equal to zero.
- the subscripts a and b are 1, and the subscripts c and d are 0.
- the indices a and c are equal to 1, and the indices b and d are equal to 0.
- A is a carbon atom.
- Y is a nitrogen atom.
- Compound of formula (I) is N, more preferably at most two groups X, and most preferably at most one group X.
- no more than 2 directly adjacent groups X in a ring are equal to N.
- X is CR 1 .
- Ar 1 and Ar 2 in each occurrence are identically or differently selected from aromatic ring systems having 6 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or heteroaromatic ring systems having 5 to 24 aromatic ring atoms, which may be substituted with one or a plurality of R 2 may be substituted. It is preferred in combination that at least one of the two groups Ar 1 and Ar 2 is an aromatic
- Ring system having 12 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or a
- heteroaromatic ring system with 12 to 24 aromatic ring atoms is, which may be substituted with one or more radicals R 2 .
- Occurrence equal or different selected from aromatic
- Ring systems having 12 to 24 aromatic ring atoms which may be substituted by one or more radicals R 2 and heteroaromatic ring systems having 12 to 24 aromatic ring atoms which may be substituted by one or more radicals R 2 .
- Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 each contain at least one group selected from benzene, naphthalene, phenanthrene, fluoranthene, biphenyl, terphenyl, quaterphenyl, fluorene, indenofluorene, spirobifluorene, furan, benzofuran, isobenzofuran , Dibenzofuran, thiophene,
- Ar 3 , Ar 4 , Ar 5 , Ar 6 on each occurrence are identically or differently selected from aromatic ring systems having 6 to 24 aromatic ring atoms which may be substituted by one or more R 2 radicals, or heteroaromatic ring systems with 5 to 24 aromatic ring atoms which may be substituted by one or more radicals R 2 .
- Preferred embodiments of the groups Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are the following groups:
- Positions can be substituted in each case with radicals R 2 , and wherein the bond marked with * represents the attachment position of the respective group.
- At least one of Ar 1 and Ar 2 is selected from one of the abovementioned groups of formulas (Ar-2) to (Ar-15) and (Ar-18) to (Ar-66).
- both Ar 1 and Ar 2 groups are selected from one of the abovementioned groups (Ar-2) to (Ar-15) and (Ar-18) to (Ar-66).
- at least one of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 comprises at least one heteroaryl group as defined above.
- the at least one heteroaryl group preferably has 5 to 20 aromatic ring atoms, more preferably 6 to 14 aromatic ring atoms.
- the radical R 1 is preferably identically or differently selected on each occurrence from H, D, F, CN, Si (R 3 ) 3, straight-chain alkyl or alkoxy groups having 1 to 10 C atoms, branched or cyclic alkyl or alkoxy groups 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; wherein said alkyl and
- the radical R at each occurrence is identically or differently selected from H, F, CN, Si (R 3 ) 3, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; wherein said aromatic ring systems and said heteroaromatic ring systems may each be substituted with one or more R 3 radicals.
- the radical R 1 is H.
- the radical R 2 is preferably identically or differently selected on each occurrence from H, D, F, CN, Si (R 3 ) 3, straight-chain alkyl or alkoxy groups having 1 to 10 C atoms, branched or cyclic alkyl or alkoxy groups 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; wherein said alkyl and
- the radical R 2 is the same or different selected on each occurrence from H, F, CN, Si (R 3 ) 3, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic
- heteroaromatic ring systems with 5 to 24 aromatic ring atoms; wherein said alkyl groups, said aromatic
- Ring systems and said heteroaromatic ring systems may each be substituted with one or more R 3 radicals.
- the radical R 3 is the same or different selected on each occurrence from H, D, F, CN, Si (R) 3, straight-chain alkyl or alkoxy groups having 1 to 10 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms; wherein said alkyl and
- the radical R 3 is the same or different selected on each occurrence from H, F, CN, Si (R 4 ) 3, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic
- heteroaromatic ring systems with 5 to 24 aromatic ring atoms; wherein said alkyl groups, said aromatic
- Ring systems and said heteroaromatic ring systems may each be substituted with one or more R 4 radicals.
- the compound of the formula (I) preferably corresponds to one of the formulas (1-1) to (I-3)
- X is CR 1 and that exactly 1, exactly 2 or exactly 3 indices are selected from the indices a, b, c and d are equal to 1.
- the compound of the formula (I) corresponds to one of the formulas (1-1-1) to (1-1-4)
- the compounds of formula (I) may be prepared using known organic chemistry reactions, for example using bromination reactions, Buchwald coupling reactions and Suzuki coupling reactions.
- a preferred method for preparing compounds of formula (I) begins with acridinone or a derivative of acridinone (Scheme 1). This is reacted in a Buchwald coupling to give acridinone substituted with an aryl group on the N. This will be in brominated in a further step, and aryl groups are introduced in a Suzuki reaction at the brominated positions. On this way
- Symmetric acridinone intermediates are preferably obtained.
- Asymmetric acridinone skeletons can be prepared according to Scheme 2
- Ar, Ar ' aromatic or heteroaromatic ring system
- the symmetrically substituted or asymmetrically substituted acridinone derivatives are substituted accordingly
- Ar aromatic or heteroaromatic ring system
- the synthesis methods described are merely preferred methods. Alternative methods are possible which can be used by the person skilled in the art within the scope of his general expertise, if necessary.
- the present invention relates to a process for the preparation of compounds of the formula (I), characterized in that it comprises the following steps:
- step 2) takes place after step 1), and step 3) takes place after step 2).
- step 3 Further preferred are derivatization and coupling reactions at step 3), for example Suzuki couplings.
- the metal organyl in step 1) is an organolithium base, particularly preferably n-butyllithium.
- step 1) a nucleophilic compound
- dienes or azides for example, dienes or azides, carboxylic acid derivatives, alcohols and silanes.
- Another object of the invention are therefore oligomers, polymers or dendrimers containing one or more compounds according to
- Formula (I), wherein the bond (s) to the polymer, oligomer or dendrimer can be located at any, in formula (I) with R 1 or R 2 substituted positions.
- the compound is part of a side chain of the oligomer or polymer or part of the backbone.
- An oligomer in the context of this invention is understood as meaning a compound which is composed of at least three monomer units.
- a polymer in the context of the invention is understood as meaning a compound which is composed of at least ten monomer units.
- the polymers, oligomers or dendrimers according to the invention may be conjugated, partially conjugated or non-conjugated.
- the oligomers or polymers of the invention may be linear, branched or dendritic.
- the units of formula (I) may be directly linked together or may be linked together via a divalent group, for example via a substituted or unsubstituted alkylene group, via a heteroatom or via a divalent aromatic or heteroaromatic group.
- three or more units of formula (I) may be linked via a trivalent or higher valent group, for example via a trivalent or higher valent aromatic or heteroaromatic group, to a branched or dendritic oligomer or polymer.
- the monomers according to the invention are homopolymerized or copolymerized with further monomers.
- Suitable and preferred comonomers are selected from fluorenes (eg according to EP 842208 or WO 2000/22026),
- cis-and trans-indenofluorenes eg according to WO 2004/041901 or WO 2004/113412
- ketones eg according to WO 2005/040302
- phenanthrenes e.g. B. according to WO 2005/104264 or WO 2007/017066
- the polymers, oligomers and dendrimers usually contain further units, For example, emitting (fluorescent or phosphorescent) units, such.
- Vinyltriarylamines for example according to WO 2007/068325
- phosphorescent metal complexes for example according to WO 2006/003000
- charge transport units especially those based on triarylamines.
- the polymers and oligomers according to the invention are generally prepared by polymerization of one or more types of monomer, of which at least one monomer in the polymer leads to repeat units of the formula (I). Suitable polymerization reactions are known in the art and described in the literature. Particularly suitable and preferred polymerization reactions which lead to C-C or C-N linkages are the following:
- Literature for example in WO 2003/048225, WO 2004/037887 and WO 2004/037887, described in detail.
- formulations of the compounds according to the invention are required. These formulations may be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene,
- Methyl benzoate mesitylene, tetralin, veratrole, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-) - fenchone, 1, 2,3,5-tetramethylbenzene, 1, 2,4,5 Tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, ⁇ -terpineol, benzothiazole, butyl benzoate, cumene,
- Triethylene glycol dimethyl ether diethylene glycol monobutyl ether
- Tripropylene glycol dimethyl ether Tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene,
- the invention therefore further provides a formulation, in particular a solution, dispersion or emulsion containing at least one compound of the formula (I) or at least one
- Polymer, oligomer or dendrimer comprising at least one unit of the formula (I) and at least one solvent, preferably an organic solvent. How such solutions can be prepared is known to the person skilled in the art and, for example, in WO
- the compounds according to the invention are suitable for use in electronic devices, in particular in organic electroluminescent devices (OLEDs). Depending on the substitution, the compounds are in different functions and layers
- Another object of the invention is therefore the use of
- the electronic device is preferably selected from the group consisting of organic integrated circuits (OICs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic light emitting transistors (OLETs),
- OICs organic integrated circuits
- OFETs organic field effect transistors
- OTFTs organic thin film transistors
- OLETs organic light emitting transistors
- organic solar cells organic solar cells
- organic optical detectors organic photoreceptors
- organic field quench devices OFQDs
- organic light-emitting electrochemical cells OECs
- O-lasers organic laser diodes
- OEDs organic electroluminescent devices
- the electronic device is preferably selected from the abovementioned devices.
- OLED organic electroluminescent device
- Hole transport layer or another layer at least one compound according to formula (I) contains.
- the organic electroluminescent device may contain further layers. These are, for example, selected from in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, intermediate layers
- the sequence of the layers of the organic electroluminescent device containing the compound of the formula (I) is preferably the following:
- the organic electroluminescent device according to the invention may contain a plurality of emitting layers.
- these emission layers particularly preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie, in the emitting layers
- Hole transport layer hole injection layer or the
- Electron blocking layer present.
- the compound according to formula (I) is used in an electronic device containing one or more phosphorescent emitting compounds.
- the compound in different layers, preferably in a hole transport layer, an electron blocking layer, a
- a spin-forbidden transition typically comprises compounds in which the light emission occurs through a spin-forbidden transition, for example, a transition from a triplet excited state or a state having a higher spin quantum number, for example, a quintet state.
- Suitable phosphorescent emissive compounds are in particular compounds which emit light, preferably in the visible range, when suitably excited, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80
- Preferred phosphorescent emissive compounds are compounds which are copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium used, in particular compounds containing iridium, platinum or copper.
- all luminescent iridium, platinum or copper complexes are used as
- the compound according to formula (I) can also according to the invention in an electronic device containing one or more
- the compounds of the formula (I) are used as hole transport material.
- Compounds are then preferably present in a hole transport layer, an electron blocking layer or a hole injection layer.
- a hole transport layer according to the present application is a hole transporting layer located between the anode and the emissive layer.
- a hole injection layer is in the case of multiple hole transport layers between anode and
- An electron blocking layer is, in the case of a plurality of hole transport layers between the anode and the emitting layer, the hole transport layer which adjoins the emitting layer directly on the anode side.
- the organic layer comprising the compound of the formula (I) then additionally contains one or more p-dopants.
- p-dopants preferably those organic electron acceptor compounds are used which can oxidize one or more of the other compounds of the mixture.
- p-dopants are those described in WO 2011/073149, EP 1968131, EP 2276085, EP 2213662, EP 1722602, EP 2045848, DE 102007031220, US 8044390, US 8057712, WO
- p-dopants are quinodimethane compounds, azaindenofluorendiones, azaphenalens, azatriphenylenes, I2,
- Metal halides preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of the 3rd main group, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one oxygen atom as a binding site. Preference is still given
- Transition metal oxides as dopants preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re2O7, M0O3, WO3 and ReO3.
- the p-dopants are preferably present largely uniformly distributed in the p-doped layers. This can be achieved, for example, by co-evaporation of the p-dopant and the hole transport material matrix.
- the compound according to formula (I) is used as hole transport material in combination with a hexaazatriphenylene derivative as described in US 2007/0092755.
- a hexaazatriphenylenderivat is used in a separate layer.
- the compound of the formula (I) is employed in an emitting layer as matrix material in combination with one or more emitting compounds, preferably phosphorescent emitting compounds.
- the proportion of the matrix material in the emitting layer in this case is between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferred for fluorescent emitting layers between 92.0 and 99.5% by volume and for phosphorescent emitting layers between 85.0 and 97.0 vol.%.
- the proportion of the emitting compound is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume and particularly preferred for fluorescent emitting layers between 0.5 and 8.0% by volume and for phosphorescent emitting layers between 3.0 and 15.0% by volume .-%.
- An emitting layer of an organic electroluminescent device may also include systems comprising a plurality of matrix materials (Mixed-matrix systems) and / or multiple emitting compounds.
- the emissive compounds are generally those compounds whose proportion in the system is smaller and the matrix materials are those compounds whose proportion in the system is larger. In individual cases, however, the proportion of a single matrix material in the system may be smaller than the proportion of a single emitting compound.
- the mixed-matrix systems preferably comprise two or three different ones
- Matrix materials more preferably two different ones
- Matrix materials In this case, one of the two materials preferably constitutes a material with hole-transporting properties and the other material is a material with electron-transporting properties.
- the compound of formula (I) preferably represents the matrix material with hole-transporting properties
- electron-transporting and hole-transporting properties of the mixed-matrix components may also be mainly or completely combined in a single mixed-matrix component, with the further or the further mixed-matrix components fulfilling other functions.
- the two different matrix materials may be present in a ratio of 1:50 to 1: 1, preferably 1:20 to 1: 1, more preferably 1:10 to 1: 1 and most preferably 1: 4 to 1: 1. Preference is given to mixed-matrix systems in
- the mixed-matrix systems may comprise one or more emitting compounds, preferably one or more
- phosphorescent emitting compounds In general, mixed-matrix systems are preferred in phosphorescent organic
- Electroluminescent devices used.
- Particularly suitable matrix materials which can be used in combination with the compounds according to the invention as matrix components of a mixed-matrix system are selected from the below-mentioned preferred matrix materials for phosphorescent emitting compounds or the preferred matrix materials for fluorescent emitting compounds, depending on which type of emitting Connection is used in the mixed-matrix system.
- Preferred phosphorescent emitting compounds are the compounds mentioned above and the compounds shown in the following table:
- Preferred fluorescent emitting compounds are, besides the compounds of formula (I), selected from the class of arylamines.
- An arylamine or an aromatic amine in the context of this invention is understood as meaning a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. At least one of these aromatic or heteroaromatic ring systems is preferably a fused ring system, more preferably at least 14 aromatic ring atoms.
- Preferred examples thereof are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.
- aromatic anthracene amine is meant a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
- an aromatic anthracenediamine is meant a compound in which two
- Diarylamino groups are attached directly to an anthracene group, preferably in the 9,10-position.
- Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, the diarylamino groups being attached to the pyrene preferably in the 1-position or in the 1,6-position.
- Further preferred emitting compounds are indenofluoreneamines or diamines, for example according to WO
- WO 2012/048780 and the pyrene-arylamines disclosed in WO 2013/185871. Also preferred are the benzoindenofluorene amines disclosed in WO 2014/037077, which were disclosed in WO 2014/106522
- matrix materials preferably for fluorescent emitting
- Preferred matrix materials are selected from the classes of oligoarylenes (for example 2,2 ', 7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligoarylenes containing condensed aromatic groups, the oligoarylenevinylenes (eg DPVBi or spiro-DPVBi according to EP 676461), the polypodal metal complexes (eg according to WO 2004/081017), the hole-conducting compounds (e.g. B. according to WO 2004/058911), the electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (eg., 2,2 ', 7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligoarylenes containing condensed aromatic groups, the oligo
- oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides.
- Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzphenanthrene and / or pyrene or atropisomers of these compounds.
- an oligoarylene is to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another. Preference is furthermore given to those in WO 2006/097208,
- WO 2006/117052 triazine derivatives, z. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexes, for. B. according to EP 652273 or WO 2009/062578, diazasilol or tetraazasilol derivatives, z. B. according to WO 2010/054729, diazaphosphole derivatives, z. B. according to WO 2010/054730, bridged carbazole derivatives, z. B. according to US 2009/0136779, WO 2010/050778, WO
- Triphenylene derivatives eg. B. according to WO 2012/048781, or lactams, z. B. according to WO 2011/116865 or WO 2011/137951.
- Suitable charge transport materials as used in the hole injection or hole transport layer or in the electron blocking layer or in the
- the compounds which can be used are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107 (4), 953-1010 or other materials as described in the prior art Technique can be used in these layers.
- the OLED according to the invention preferably comprises two or more
- the compound of formula (I) may be in one or more or all
- hole transporting layers are used. According to one
- the compound of the formula (I) is used in exactly one hole-transporting layer, and in the other hole-transporting layers that are present, others are used
- materials for the electron transport layer it is possible to use all materials as used in the prior art as electron transport materials in the electron transport layer.
- aluminum complexes for example Alq3, zirconium complexes, for example Zrq4, lithium complexes, for example Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives,
- Oxadiazole derivatives aromatic ketones, lactams, boranes, Diazaphospholderivate and Phosphinoxidderivate.
- Further suitable materials are derivatives of the abovementioned compounds, as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300.
- Preferred as the cathode of the electronic device are low workfunction metals, metal alloys or multilayer structures of various metals, such as alkaline earth metals, alkali metals, main group metals or lanthanides (eg Ca, Ba, Mg, Al, In, Mg, Yb, Sm, Etc.).
- alloys of an alkali or alkaline earth metal and silver for example an alloy of magnesium and silver.
- further metals which have a relatively high work function such as, for example, As Ag or Al, which then usually combinations of metals, such as Ca / Ag, Mg / Ag or Ba / Ag are used.
- metals such as Ca / Ag, Mg / Ag or Ba / Ag are used.
- Alkaline earth metal fluorides but also the corresponding oxides or
- Carbonates in question eg. B. LiF, L12O, BaF 2, MgO, NaF, CsF, Cs2CO3, etc.
- lithium quinolinate LiQ
- the layer thickness of this layer is preferably between 0.5 and 5 nm.
- the anode high workfunction materials are preferred.
- the anode has a work function greater than 4.5 eV. Vacuum up.
- metals with a high redox potential such as Ag, Pt or Au, are suitable for this purpose.
- metal / metal oxide electrodes eg Al / Ni / NiOx, Al / PtOx
- at least one of the electrodes must be transparent or
- anode material is conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is furthermore given to conductive, doped organic materials, in particular conductive doped ones Polymers.
- the anode can also consist of several layers, for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide,
- Molybdenum oxide or vanadium oxide The device is structured accordingly (depending on the application), contacted and finally sealed to exclude harmful effects of water and air.
- the electronic device is characterized in that one or more layers are coated with a sublimation process.
- the materials in vacuum sublimation systems become smaller at an initial pressure
- Carrier gas sublimation are coated.
- the materials are applied at a pressure between 10 "applied 5 mbar and 1 bar.
- a special case of this method is the OVJP (organic vapor jet printing) method in which the materials are applied directly through a nozzle and patterned (eg. BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
- the electronic devices comprising one or more compounds of the formula (I) can be used in displays, as light sources in illumination applications and as light sources in medical and / or cosmetic applications (eg light therapy).
- Step 1
- Residue is recrystallized from toluene / heptane.
- A-2) Synthesis of Asymmetric Acridinones Step 1: 50 g (155.5 mmol) of bis-biphenyl-4-yl-amine, 66.9 g (311.1 mmol) of methyl 2-bromo-benzoate, 21.5 g (155.5 mmol) of potassium carbonate, 22.1 g (155.5 mmol), sodium sulfate and 0.9 g (15.5 mmol) of copper powder are suspended in 210 mL of nitrobenzene. The reaction mixture is heated to 220 ° C. for 6 h. After cooling, it is filtered through Celite and distilled off the nitrobenzene. The residue is filtered through silica gel
- Citric acid solution and extracted with acetic acid ester.
- the combined organic phases are dried and concentrated in vacuo. The residue is used in the next step without further purification.
- inventive OLEDs and OLEDs according to the prior art is carried out according to a general method according to WO 04/058911, which is adapted to the conditions described here (for example materials).
- inventive examples E1-E16 and in the reference examples V1-V4 the data of different OLEDs are presented.
- the substrates used are glass plates coated with structured ITO (indium tin oxide) of thickness 50 nm.
- the OLEDs have the following layer structure: substrate / p-doped
- HIL Hole injection layer
- HTL hole transport layer
- EBL emission layer
- ETL electron transport layer
- EIL electron injection layer
- cathode is formed by a 100 nm thick aluminum layer.
- the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (Dotand, emitter), which is added to the matrix material or the matrix materials by co-evaporation in a certain volume fraction.
- the electron transport layers or the hole injection layers may consist of a mixture of two or more materials.
- the OLEDs are characterized by default.
- the electroluminescence spectra and the current efficiency (in cd / A) are measured, the power efficiency and the external quantum efficiency (EQE, in percent) as a function of the luminance from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian
- EQE @ 10 mA / cm 2 denotes the external quantum efficiency at a current density of 10 mA / cm 2 .
- LD80 @ 60 mA / cm 2 is the life that up to which the OLED is dropped 2 cm at an initial luminance at a constant current of 60 mA / to 80% of the initial intensity.
- HIM F4TCNQ (S%) HTMV2 H1: SEB (5%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM5 H1: SEB (5%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%)
- HIM HTMV2 F4TCNQ (5%)
- HTMV2 H2 TEG (10%)
- ETM LiQ (50%) LiQ
- HTM5 F4TCNQ (5%) HTM5 H2: TEG (10%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTMV1 H1: SEB (5%) ETM: LiQ (50%) UQ
- HIM F4TCNQ (5%) HIM HTM1 H1: SEB (5%) ETM: ÜQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM2 H1: SEB (5%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM3 H1: SEB (5%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM4 H1: SEB (5%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM6 H1: SEB (5%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM7 H1: SEB (5%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM8 H1: SEB (5%) ETM: LiQ (50%) UQ
- HIM F4TCNQ (5%)
- HIM HTMV1 F4TCNQ (5%)
- HTMV1 H2 TEG (10%)
- ETM LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM1: F4TCNQ (5%) HTM1 H2: TEG (10%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM2: F4TCNQ (5%) HTM2 H2: TEG (10%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM3: F4TCNQ (5%) HTM3 H2: TEG (10%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM4: F4TCNQ (5%) HTM4 H2: TEG (10%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM6: F4TCNQ (5%) HTM6 H2: TEG (10%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM7: F4TCNQ (5%) HTM7 H2: TEG (10%) ETM: LiQ (50%) LiQ
- HIM F4TCNQ (5%) HIM HTM8: F4TCNQ (5%) HTM8 H2: TEG (10%) ETM: LiQ (50%) LiQ
- Example 1 a substance of the invention (HTM5) and the prior art (HTMV2) in an OLED with blue fluorescent
- the external quantum efficiency at 10 mA / cm 2 of the compound according to the invention from the samples E1 is significantly better with 8.5% than that of the reference sample V1 with only 6.0%.
- the lifetime LD80 at 10 mA / cm 2 of the compound according to the invention from the samples E1 is significantly better with 8.5% than that of the reference sample V1 with only 6.0%.
- 60mA / cm 2 is significantly increased in the inventive sample E1 with 115h compared to the prior art in V1 with 38h.
- the two substances are also compared in a triplet green component.
- the reference sample V2 shows 16.3% a significantly lower quantum efficiency at 2mA / cm 2 than the inventive sample E2 with 20.1%.
- the lifetime LD80 of the sample E2 according to the invention, at 223h, is significantly above the reference lifetime of V2 at 96h.
- Example 2 a further four substances according to the invention (HTM1, HTM2, HTM3 and HTM4) are compared with the prior art (HTMV1).
- sample E3 according to the invention achieves a higher quantum efficiency of 9.8% at 10 mA / cm 2 than the prior art (V3) of 8.5%.
- the lifetimes (80%) of the components with materials E3-E6 according to the invention are markedly above the lifetime of the E3 (214h), E4 (180h), E5 (154h) and E6 (166h)
- the reference sample V4 (.8%) shows a lower quantum efficiency at 2 mA / cm 2 than, for example, the
- inventive sample E10 (20.4%). Also, the lifetimes (80%) at 20 mA / cm 2 of the inventive samples E10 (199h), E11 (223h), E12 (205h), and E13 (214h) are higher than in prior art V4 with only 193h.
- HTM6, HTM7 and HTM8 are compared with the prior art (HTMV1).
- samples E8 according to the invention with 8.6% at 10 mA / cm 2 and E 9 with 9.1% achieve a higher quantum efficiency than the prior art (V 3) with 8.5%.
- the service life (80%) of the component with material E8 according to the invention is 150h, well above the life of the comparison component V3 with 66h.
- the reference sample V4 (19.8%) exhibits a lower quantum efficiency at 2 mA / cm 2 than the inventive samples E14 (21, 5%), E15 (20.2%) and E16 (20, 6%).
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Abstract
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US15/303,390 US10374168B2 (en) | 2014-04-14 | 2015-03-19 | Materials for electronic devices |
EP15711049.5A EP3131901B1 (de) | 2014-04-14 | 2015-03-19 | Materialien für elektronische vorrichtungen |
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Also Published As
Publication number | Publication date |
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EP3131901A1 (de) | 2017-02-22 |
US10374168B2 (en) | 2019-08-06 |
US20170125701A1 (en) | 2017-05-04 |
CN106164074A (zh) | 2016-11-23 |
JP2017513855A (ja) | 2017-06-01 |
TWI664171B (zh) | 2019-07-01 |
EP3131901B1 (de) | 2018-02-07 |
JP6651460B2 (ja) | 2020-02-19 |
KR102375983B1 (ko) | 2022-03-17 |
KR20160143821A (ko) | 2016-12-14 |
CN106164074B (zh) | 2019-01-18 |
TW201602091A (zh) | 2016-01-16 |
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