CN113728453A - 电子器件 - Google Patents
电子器件 Download PDFInfo
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- CN113728453A CN113728453A CN202080030031.5A CN202080030031A CN113728453A CN 113728453 A CN113728453 A CN 113728453A CN 202080030031 A CN202080030031 A CN 202080030031A CN 113728453 A CN113728453 A CN 113728453A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 239000000463 material Substances 0.000 claims description 51
- 230000005525 hole transport Effects 0.000 claims description 48
- 238000002347 injection Methods 0.000 claims description 33
- 239000007924 injection Substances 0.000 claims description 33
- 150000003254 radicals Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 15
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000002019 doping agent Substances 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
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- 125000003277 amino group Chemical group 0.000 description 6
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- 125000004986 diarylamino group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
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- 125000006574 non-aromatic ring group Chemical group 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
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- 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 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
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- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
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- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 1
- ALGIYXGLGIECNT-UHFFFAOYSA-N 3h-benzo[e]indole Chemical class C1=CC=C2C(C=CN3)=C3C=CC2=C1 ALGIYXGLGIECNT-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- OTTYHRLXKGOXLY-UHFFFAOYSA-N 9h-xanthen-9-amine Chemical compound C1=CC=C2C(N)C3=CC=CC=C3OC2=C1 OTTYHRLXKGOXLY-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L Cs2CO3 Substances [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 229910002842 PtOx Inorganic materials 0.000 description 1
- 229910019571 Re2O7 Inorganic materials 0.000 description 1
- 229910002785 ReO3 Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical class [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 229910000573 alkali metal alloy Inorganic materials 0.000 description 1
- 229910000941 alkaline earth metal alloy Inorganic materials 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- 150000001621 bismuth Chemical class 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- JDIBGQFKXXXXPN-UHFFFAOYSA-N bismuth(3+) Chemical class [Bi+3] JDIBGQFKXXXXPN-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000005621 boronate group Chemical class 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
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- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- SWGQKRKXZZPKJA-UHFFFAOYSA-N indeno[2,1-a]fluorene-1,2-diamine Chemical class C1=CC=C2C=C3C4=CC5=C(N)C(N)=CC=C5C4=CC=C3C2=C1 SWGQKRKXZZPKJA-UHFFFAOYSA-N 0.000 description 1
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000000025 interference lithography Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
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- 239000003550 marker Substances 0.000 description 1
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- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 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
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 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
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 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
- 150000003230 pyrimidines Chemical class 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
- 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
- 229910052707 ruthenium Inorganic materials 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
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003457 sulfones 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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
本申请涉及一种包含有机层的电子器件,该有机层又含有至少两种不同化合物的混合物。
Description
本申请涉及一种电子器件,所述电子器件依次包含阳极、空穴注入层、空穴传输层、发光层和阴极。所述空穴传输层含有选自螺二芴胺和芴胺化合物的第一化合物,以及不同于所述第一化合物并且选自螺二芴胺和芴胺化合物的第二化合物。
本申请上下文中的电子器件被理解为是指所谓的有机电子器件,其含有有机半导体材料作为功能材料。更特别地,这些被理解为是指OLED(有机发光二极管,有机电致发光器件)。这些电子器件具有一个或多个包含有机化合物的层并且在施加电压时发光。OLED的构造和工作的一般原理是本领域技术人员已知的。
空穴注入层被理解为是指在电子器件的运行中支持空穴从OLED的阳极注入到空穴传输层中的层。空穴注入层优选直接邻接阳极,并且在阴极侧有一个或多个空穴传输层直接邻接空穴注入层。
空穴传输层被理解为是能够在电子器件的运行中传输空穴的层。更特别地,它是在OLED中布置在阳极和最接近阳极的发光层之间的层。
在电子器件,尤其是OLED中,对于改善性能数据,尤其是寿命、效率、工作电压和色纯度,有很大的兴趣。在这些方面,尚未能找到任何完全令人满意的解决方案。
空穴传输层对电子器件的上述性能数据有很大影响。它们可作为阳极和发光层之间的单独空穴传输层存在,或者以阳极和发光层之间的多个空穴传输层,例如2或3个空穴传输层的形式存在。
现有技术中已知的空穴传输层材料主要是胺化合物,尤其是三芳基胺化合物。这样的三芳胺化合物的例子是螺二芴胺、芴胺、茚并芴胺、菲胺、咔唑胺、呫吨胺、螺二氢吖啶胺、联苯胺以及这些具有一个或多个氨基基团的结构元件的组合,这只是一个选集,本领域技术人员知晓其它的结构类别。
现已发现依次包含阳极、空穴注入层、空穴传输层、发光层和阴极的电子器件,其中空穴传输层含有选自螺二芴胺和芴胺化合物的第一化合物以及选自螺二芴胺和芴胺化合物的与第一化合物不同的第二化合物,所述电子器件与其中空穴传输层由单一化合物形成的现有技术电子器件相比,具有更好的性能数据。更特别地,与上述现有技术的器件相比,这样的器件的寿命和/或效率得到改善。
本申请由此提供了一种电子器件,其包含
-阳极,
-阴极,
-布置在阳极和阴极之间的发光层,
-布置在阳极和发光层之间的空穴注入层;
-布置在空穴注入层和发光层之间并且在阳极侧直接邻接发光层的空穴传输层,并且其含有两种符合选自式(I)和(II)的相同或不同式的不同化合物,
其中
X在每次出现时相同或不同并且选自单键、O、S、C(R1)2和NR1;
Ar1和Ar2在每次出现时相同或不同并且选自具有6至40个芳族环原子并且被一个或多个R2基团取代的芳族环系、以及具有5至40个芳族环原子并且被一个或多个R2基团取代的杂芳族环系;
R1和R2在每次出现时相同或不同并且选自:H,D,F,Cl,Br,I,C(=O)R3,CN,Si(R3)3,N(R3)2,P(=O)(R3)2,OR3,S(=O)R3,S(=O)2R3,具有1至20个碳原子的直链的烷基或烷氧基基团,具有3至20个碳原子的支链或环状的烷基或烷氧基基团,具有2至20个碳原子的烯基或炔基基团,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中两个或更多个R1或R2基团可彼此连接并且可形成环;其中所提及的烷基、烷氧基、烯基和炔基基团以及所提及的芳族环系和杂芳族环系各自被R3基团取代;并且其中所提及的烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可被-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO或SO2代替;
R3在每次出现时相同或不同并且选自:H,D,F,Cl,Br,I,CN,具有1至20个碳原子的烷基或烷氧基基团,具有2至20个碳原子的烯基或炔基基团,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中两个或更多个R3基团可彼此连接并且可形成环;并且其中所提及的烷基、烷氧基、烯基和炔基基团、芳族环系和杂芳族环系可被一个或多个选自F和CN的基团取代;
n是0、1、2、3或4,其中,当n=0时,Ar1基团不存在并且氮原子直接与该式的其余部分键合。
当n=2时,两个Ar1基团成功地连续键合,为-Ar1-Ar1-。当n=3时,三个Ar1基团成功地连续键合,为-Ar1-Ar1-Ar1-。当n=4时,四个Ar1基团成功地连续键合,为-Ar1-Ar1-Ar1-Ar1-。
以下定义可适用于本申请中使用的化学基团。除非给出任何更具体的定义,否则它们均可适用。
本发明上下文中的芳基基团被理解为是指单芳族环,即苯,或稠合芳族多环,例如萘、菲或蒽。本申请上下文中的稠合芳族多环由两个或更多个彼此稠合的单芳族环组成。环之间的稠合在此被理解为是指所述环彼此共有至少一条边。本发明上下文中的芳基基团含有6至40个芳族环原子。另外,芳基基团不含任何杂原子作为芳族环原子。
本发明上下文中的杂芳基基团被理解为是指单杂芳族环,例如吡啶、嘧啶或噻吩,或稠合杂芳族多环,例如喹啉或咔唑。本申请上下文中的稠合杂芳族多环由两个或更多个彼此稠合的单芳族或杂芳族环组成,其中所述芳族和杂芳族环中的至少一个是杂芳族环。环之间的稠合在此被理解为是指所述环彼此共有至少一条边。本发明上下文中的杂芳基基团含有5至40个芳族环原子,其中至少一个是杂原子。所述杂芳基基团的杂原子优选选自N、O和S。
各自可被上述基团取代的芳基或杂芳基基团尤其被理解为是指衍生自下列物质的基团:苯、萘、蒽、菲、芘、二氢芘、苣、苝、联三苯叉、荧蒽、苯并蒽、苯并菲、并四苯、并五苯、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩嗪、吡唑、吲唑、咪唑、苯并咪唑、苯并咪唑并[1,2-a]苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲哚嗪和苯并噻二唑。
本发明上下文中的芳族环系是如下的体系,其不必只含有芳基基团,而是还可含有一个或多个与至少一个芳基基团稠合的非芳族环。这些非芳族环仅含碳原子作为环原子。该定义所涵盖的基团的例子是四氢萘、芴和螺二芴。另外,术语“芳族环系”包括由两个或更多个经由单键彼此连接的芳族环系组成的体系,例如联苯、三联苯、7-苯基-2-芴基、四联苯和3,5-二苯基-1-苯基。本发明上下文中的芳族环系含有6至40个碳原子并且在该环系中没有杂原子。“芳族环系”的定义不包括杂芳基基团。
杂芳族环系符合上述的芳族环系定义,不同之处在于它必须含有至少一个杂原子作为环原子。如同芳族环系的情况,杂芳族环系不必仅含有芳基基团和杂芳基基团,而是还可含有一个或多个与至少一个芳基或杂芳基基团稠合的非芳族环。所述非芳族环可仅含碳原子作为环原子,或者它们还可含有一个或多个杂原子,其中所述杂原子优选选自N、O和S。这样的杂芳族环系的一个例子是苯并吡喃基。另外,术语“杂芳族环系”被理解为是指由两个或更多个经由单键彼此键合的芳族或杂芳族环系组成的体系,例如4,6-二苯基-2-三嗪基。本发明上下文中的杂芳族环系含有5至40个选自碳和杂原子的环原子,其中至少一个环原子是杂原子。所述杂芳族环系的杂原子优选选自N、O和S。
因此,如本申请中定义的术语“杂芳族环系”和“芳族环系”彼此的不同在于,芳族环系不能有杂原子作为环原子,而杂芳族环系必须有至少一个杂原子作为环原子。该杂原子可作为非芳族杂环的环原子或作为芳族杂环的环原子存在。
根据以上定义,任何芳基基团均被术语“芳族环系”涵盖,并且任何杂芳基基团均被术语“杂芳族环系”涵盖。
具有6至40个芳族环原子的芳族环系或具有5至40个芳族环原子的杂芳族环系尤其被理解为是指衍生自上述在芳基基团和杂芳基基团下提及的基团的基团,以及衍生自联苯、三联苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、茚并芴、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、茚并咔唑的基团,或衍生自这些基团的组合的基团。
在本发明的上下文中,其中个别的氢原子或CH2基团也可被上述在该基团的定义下提及的基团取代的具有1至20个碳原子的直链烷基基团、具有3至20个碳原子的支链或环状的烷基基团和具有2至40个碳原子的烯基或炔基基团优选被理解为是指甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环已烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基基团。
其中个别的氢原子或CH2基团也可被上述在该基团的定义下提及的基团代替的具有1至20个碳原子的烷氧基或硫代烷基基团优选被理解为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。
在本发明的上下文中,两个或更多个基团一起可形成环的措辞,应被理解为尤其是指所述两个基团通过化学键彼此连接。然而,另外,上述措辞也应被理解为是指,如果所述两个基团之一是氢,则第二个基团结合到该氢原子键合的位置,从而形成环。
所述电子器件优选是有机电致发光器件(OLED)。
优选的阳极是具有高逸出功的材料。优选地,阳极具有相对于真空大于4.5eV的逸出功。首先,适于此目的的是具有高氧化还原电位的金属,例如Ag、Pt或Au。其次,也可优选金属/金属氧化物电极(例如Al/Ni/NiOx、Al/PtOx)。对于一些应用而言,电极的至少一个应该是透明或部分透明的,以促进有机材料的照射(有机太阳能电池)或发光(OLED,O-激光器)。这里优选的阳极材料是导电混合金属氧化物。特别优选的是氧化锡铟(ITO)或氧化铟锌(IZO)。此外优选的是导电掺杂有机材料,尤其是导电掺杂聚合物。另外,阳极也可由两个或更多个层组成,例如由ITO的内层和金属氧化物的外层组成,所述金属氧化物优选钨氧化物、钼氧化物或钒氧化物。
所述电子器件的优选的阴极是具有低逸出功的金属、由多种金属构成的金属合金或多层结构,例如碱土金属、碱金属、主族金属或镧系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)。此外合适的是由碱金属或碱土金属与银构成的合金,例如由镁和银构成的合金。在多层结构的情况下,除了所提及的金属之外,还可以使用具有相对高逸出功的其它金属,例如Ag或Al,在这种情况下通常使用所述金属的组合,例如Ca/Ag、Mg/Ag或Ba/Ag。也可优选在金属阴极和有机半导体之间引入具有高介电常数的材料的薄中间层。对此目的有用的材料的例子是碱金属或碱土金属的氟化物、以及相应的氧化物或碳酸盐(例如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3等)。为此目的也可以使用喹啉锂(LiQ)。该层的层厚度优选在0.5nm和5nm之间。
所述器件的发光层可以是荧光或磷光发光层。所述器件的发光层优选是荧光发光层,尤其优选发蓝色荧光的发光层。在荧光发光层中,发光体优选是单重态发光体,即从在器件运行中激发单重态发光的化合物。在磷光发光层中,发光体优选是三重态发光体,即在器件工作中从激发三重态、或从具有更高自旋量子数的状态例如五重态发光的化合物。
在一个优选实施方式中,使用的荧光发光层是发蓝色荧光的层。
在一个优选实施方式中,使用的磷光发光层是发绿色或红色磷光的发光层。
合适的磷光发光体尤其是这样的化合物:其在被适当激发时发射优选在可见光区域内的光,并且还含有至少一个原子序数大于20,优选大于38且小于84,更优选大于56且小于80的原子。优选用作磷光发光体的是含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,尤其是含有铱、铂或铜的化合物。
一般而言,根据现有技术用于磷光OLED且为电致发光器件领域的本领域技术人员所知的所有磷光络合物都适合用于本发明的器件中。
下表显示了用作磷光发光体的优选化合物:
优选的荧光发光化合物选自芳基胺类。本发明上下文中的芳基胺或芳族胺被理解为是指含有三个直接与氮键合的取代或未取代的芳族或杂芳族环系的化合物。优选地,这些芳族或杂芳族环系中的至少一个是稠合环系,更优选具有至少14个芳族环原子的稠合环系。上述优选的例子是芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族苣胺或芳族苣二胺。芳族蒽胺被理解为是指其中一个二芳基氨基基团与蒽基团直接键合,优选在9位上直接键合的化合物。芳族蒽二胺被理解为是指其中两个二芳基氨基基团与蒽基团直接键合,优选在9,10位上直接键合的化合物。芳族芘胺、芘二胺、苣胺和苣二胺的定义类似,其中所述二芳基氨基基团优选在1位或在1,6位与芘键合。其它优选的发光化合物是茚并芴胺或茚并芴二胺,苯并茚并芴胺或苯并茚并芴二胺,和二苯并茚并芴胺或二苯并茚并芴二胺,以及具有稠合芳基基团的茚并芴衍生物。同样优选的是芘芳基胺。同样优选的是苯并茚并芴胺、苯并芴胺、扩展的苯并茚并芴、吩嗪和与呋喃单元或噻吩单元连接的芴衍生物。
下表显示了用作荧光发光体的优选化合物:
在一个优选实施方式中,所述电子器件的发光层含有正好一种基质化合物。基质化合物被理解为是指不是发光化合物的化合物。这种实施方式在荧光发光层的情况下尤为优选。
在一个替代的优选实施方式中,所述电子器件的发光层含有正好两种或更多种,优选正好两种基质化合物。这种实施方式,也被称为混合基质体系,在磷光发光层的情况下尤为优选。
在磷光发光层的情况下,所有基质材料的总比例优选在50.0%和99.9%之间,更优选在80.0%和99.5%之间,最优选在85.0%和97.0%之间。
以%计的比例数字在此被理解为在由气相施加的层的情况下是指以体积%计的比例,以及在由溶液施加的层的情况下是指以重量%计的比例。
相应地,磷光发光化合物的比例优选在0.1%和50.0%之间,更优选在0.5%和20.0%%之间,最优选在3.0%和15.0%之间。
在荧光发光层的情况下,所有基质材料的总比例优选在50.0%和99.9%之间,更优选在80.0%和99.5%之间,最优选在90.0%和99.0%之间。
相应地,荧光发光化合物的比例在0.1%和50.0%之间,更优选在0.5%和20.0%%之间,最优选在1.0%和10.0%之间。
混合基质体系优选包含两种或三种不同的基质材料,更优选两种不同的基质材料。优选地,在这种情况下,两种材料之一是性质包括空穴传输性质的材料,而另一种材料是性质包括电子传输性质的材料。可存在于混合基质体系中的其它基质材料是在HOMO和LUMO之间具有大能量差的化合物(宽带隙材料)。所述两种不同的基质材料可按1:50至1:1,优选1:20至1:1,更优选1:10至1:1并且最优选1:4至1:1的比率存在。优选的是在磷光有机电致发光器件中使用混合基质体系。
用于荧光发光化合物的优选的基质材料选自以下类别:低聚芳亚基(例如2,2',7,7'-四苯基螺二芴),尤其是含有稠合芳族基团的低聚芳亚基,低聚芳亚基乙烯亚基,多足金属络合物,空穴传导化合物,电子传导化合物,尤其是酮、氧化膦和亚砜;阻转异构体,硼酸衍生物,和苯并蒽。特别优选的基质材料选自以下的类别:包含萘、蒽、苯并蒽和/或芘或这些化合物的阻转异构体的低聚芳亚基,低聚芳亚基乙烯亚基,酮,氧化膦,和亚砜。非常特别优选的基质材料选自以下的类别:包含蒽、苯并蒽、苯并菲和/或芘或这些化合物的阻转异构体的低聚芳亚基。本发明上下文中的低聚芳亚基应该被理解为是指其中至少三个芳基或芳亚基基团彼此键合的化合物。
下表显示了用于荧光发光化合物的优选的基质材料:
用于磷光发光体的优选的基质材料是芳族酮,芳族氧化膦或者芳族亚砜或砜,三芳基胺,咔唑衍生物,例如CBP(N,N-双咔唑基联苯),吲哚并咔唑衍生物,茚并咔唑衍生物,氮杂咔唑衍生物,双极性基质材料,硅烷,氮杂硼杂环戊二烯或硼酸酯,三嗪衍生物,锌络合物,二氮杂硅杂环戊二烯或四氮杂硅杂环戊二烯衍生物,二氮杂磷杂环戊二烯衍生物,桥连咔唑衍生物,联三苯叉衍生物,或内酰胺。
在一个优选实施方式中,所述电子器件含有正好一个发光层。
在一个替代的优选实施方式中,所述电子器件含有多个发光层,优选2、3或4个发光层。这对于白色发光型电子器件尤为优选。
更优选地,在这种情况下发光层总体上在380nm和750nm之间具有若干个发光峰值,使得电子器件发白色光;换言之,在发光层中使用了可以发荧光或发磷光并且发蓝色、绿色、黄色、橙色或红色光的多种发光化合物。尤其优选的是三层体系,即具有三个发光层的体系,其中在每种情况下三个层中的一个显示蓝色发光,在每种情况下三个层中的一个显示绿色发光,并且在每种情况下三个层中的一个显示橙色或红色发光。为了产生白色光,也可以使用在宽波长范围内发光的单一发光体化合物,而不是多种发有色光的发光体化合物。
在本发明的一个优选实施方式中,所述电子器件包含两个或三个,优选三个相同或不同的层序列,所述层序列是一个层叠在另一个上面,其中每个层序列包含以下层:空穴注入层、空穴传输层、电子阻挡层、发光层和电子传输层,并且其中至少一个,优选全部的层序列包含下列层:
-布置在阳极和发光层之间的空穴注入层;
-布置在空穴注入层和发光层之间并且在阳极侧直接邻接发光层的空穴传输层,其含有两种符合选自式(I)和(II)的相同或不同式的不同化合物。
优选在每种情况下在所述层序列之间布置由邻接的n-CGL和p-CGL构成的双层,其中n-CGL布置在阳极侧,而p-CGL相应地在阴极侧。CGL在此表示电荷产生层。用于这样的层的材料是本领域技术人员已知的。优选在p-CGL中使用p型掺杂的胺,更优选选自下文提及的优选的空穴传输材料结构类别中的材料。
所述空穴传输层的层厚度优选为20nm至300nm,更优选为30nm至250nm。进一步优选所述空穴传输层的层厚度不大于250nm。
优选地,所述空穴传输层含有正好2、3或4种,优选正好2或3种,最优选正好2种符合选自式(I)和(II)的相同或不同式的不同化合物。
优选地,所述空穴传输层由符合选自式(I)和(II)的相同或不同式的化合物组成。“由…组成”在此被理解为是指层中不存在其它化合物,在OLED的制造过程中通常出现的少量杂质不算作层中的其它化合物。
在一个替代的优选实施方式中,除了所述符合选自式(I)和(II)的相同或不同式的化合物外,所述空穴传输层还含有p型掺杂剂。
本发明使用的p型掺杂剂优选是那些能够氧化所述混合物中一种或多种的其它化合物的有机电子受体化合物。
特别优选的p型掺杂剂是醌二甲烷化合物,氮杂茚并芴二酮,氮杂非那烯,氮杂联三苯叉,I2,金属卤化物,优选过渡金属卤化物,金属氧化物,优选含有至少一种过渡金属或第3主族金属的金属氧化物,以及过渡金属络合物,优选Cu、Co、Ni、Pd和Pt与含有至少一个氧原子作为键合位点的配体的络合物。进一步优选的是过渡金属氧化物作为掺杂剂,优选铼、钼和钨的氧化物,更优选Re2O7、MoO3、WO3和ReO3。更进一步优选的是处于(III)氧化态的铋的络合物,更特别是具有缺电子配体,更特别是羧酸盐配体的铋(III)络合物。
所述p型掺杂剂优选在p型掺杂层中基本上均匀分布。例如,这可以通过p型掺杂剂和空穴传输材料基质的共蒸发来实现。p型掺杂剂优选以1%至10%的比例存在于p型掺杂层中。
优选的p型掺杂剂尤其是以下化合物:
在本发明的一个优选实施方式中,所述空穴传输层含有两种符合式(I)的不同化合物。
所述两种符合选自式(I)和(II)的相同或不同式的不同化合物优选各自以至少5%的比例存在于空穴传输层中。它们更优选以至少10%的比例存在。优选所述化合物中的一种以比另一种化合物更高的比例存在,更优选以高达另一种化合物比例的二至五倍的比例存在。当所述空穴传输层含有正好两种符合选自式(I)和(II)的相同或不同式的化合物时,尤其如此。优选地,所述化合物中的一种在层中的比例为15%至35%,所述两种化合物中的另一种在层中的比例为65%至85%。
在式(I)和(II)当中,优选的是式(I)。
式(I)和/或(II)受一个或多个,优选所有选自以下优选中的优选项影响:
在一个优选实施方式中,所述化合物具有单个氨基基团。氨基基团被理解为是指所具有的氮原子具有三个结合配偶体的基团。这优选被理解为是指其中三个选自芳族和杂芳族基团的基团与氮原子结合的基团。
在一个替代的优选实施方式中,所述化合物正好具有两个氨基基团。
X优选是单键;
Ar1优选在每次出现时相同或不同,并且选自衍生自以下的二价基团:苯、联苯、三联苯、萘、芴、茚并芴、茚并咔唑、螺二芴、二苯并呋喃、二苯并噻吩和咔唑,所述二价基团各自被一个或多个R2基团取代。最优选地,Ar1在每次出现时相同或不同,并且是衍生自苯的二价基团,所述二价基团在每种情况下被一个或多个R2基团取代。Ar1基团在每次出现时可相同或不同。
标记n优选是0、1或2,更优选0或1,最优选0。在n=1的情况下优选的-(Ar1)n-基团符合以下式:
其中虚线表示与式的其余部分连接的键,并且其中显示为未取代的位置处的基团各自被R2基团取代,其中这些位置中的R2基团优选是H。
Ar2基团优选在每次出现时相同或不同并且选自衍生自以下的一价基团:苯,联苯,三联苯,四联苯,萘,芴,尤其是9,9'-二甲基芴和9,9'-二苯基芴,9-硅杂芴,尤其是9,9'-二甲基-9-硅杂芴和9,9'-二苯基-9-硅杂芴,苯并芴,螺二芴,茚并芴,茚并咔唑,二苯并呋喃,二苯并噻吩,苯并咔唑,咔唑,苯并呋喃,苯并噻吩,吲哚,喹啉,吡啶,嘧啶,吡嗪,哒嗪,和三嗪;其中所述一价基团各自被一个或多个R2基团取代。或者,Ar2基团在每次出现时相同或不同并且可优选选自衍生自以下的基团的组合:苯,联苯,三联苯,四联苯,萘,芴,尤其是9,9'-二甲基芴和9,9'-二苯基芴,9-硅杂芴,尤其是9,9'-二甲基-9-硅杂芴和9,9'-二苯基-9-硅杂芴,苯并芴,螺二芴,茚并芴,茚并咔唑,二苯并呋喃,二苯并噻吩,咔唑,苯并呋喃,苯并噻吩,吲哚,喹啉,吡啶,嘧啶,吡嗪,哒嗪,和三嗪;其中所述基团各自被一个或多个R2基团取代。
特别优选的Ar2基团在每次出现时相同或不同并且选自:苯基,联苯,三联苯,四联苯,萘基,芴基,尤其是9,9'-二甲基芴基和9,9'-二苯基芴基,苯并芴基,螺二芴基,茚并芴基,茚并咔唑基,二苯并呋喃基,二苯并噻吩基,咔唑基,苯并呋喃基,苯并噻吩基,苯并稠合的二苯并呋喃基,苯并稠合的二苯并噻吩基,萘基取代的苯基,芴基取代的苯基,螺二芴基取代的苯基,二苯并呋喃基取代的苯基,二苯并噻吩基取代的苯基,咔唑基取代的苯基,吡啶基取代的苯基,嘧啶基取代的苯基,和三嗪基取代的苯基;其中所提及的基团各自被一个或多个R2基团取代。
特别优选的Ar2基团相同或不同并且选自以下式:
其中显示为未取代的位置处的基团被R2基团取代,其中这些位置中的R2优选是H,并且其中虚线键是与氨基的氮原子连接的键。
优选地,R1和R2在每次出现时相同或不同并且选自:H,D,F,CN,Si(R3)3,N(R3)2,具有1至20个碳原子的直链的烷基或烷氧基基团,具有3至20个碳原子的支链或环状的烷基或烷氧基基团,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中所提及的烷基和烷氧基基团、所提及的芳族环系以及所提及的杂芳族环系各自被R3基团取代;并且其中在所提及的烷基或烷氧基基团中的一个或多个CH2基团可被-C≡C-、R3C=CR3-、Si(R3)2、C=O、C=NR3、-NR3-、-O-、-S-、-C(=O)O-或-C(=O)NR3-代替。
更优选地,R1在每次出现时相同或不同并且选自:H,D,F,CN,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中所提及的芳族环系和所提及的杂芳族环系各自被R3基团取代。
更优选地,R2在每次出现时相同或不同并且选自:H,D,F,CN,Si(R3)4,具有1至10个碳原子的直链烷基基团,具有3至20个碳原子的支链或环状的烷基基团,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中所提及的烷基基团、所提及的芳族环系以及所提及的杂芳族环系各自被R3基团取代。
特别优选的是:
-X是单键;
-Ar1在每次出现时相同或不同并且是衍生自于苯的二价基团,所述二价基团在每种情况下被一个或多个R2基团取代;
-标记n是0或1;
-Ar2在每次出现时相同或不同并且选自上述的式Ar2-1至Ar2-272;
-R1在每次出现时相同或不同并且选自:H,D,F,CN,具有6至40个芳族环原子的芳族环系,和具有5至40个芳族环原子的杂芳族环系;其中所提及的芳族环系和所提及的杂芳族环系各自被R3基团取代;
-R2在每次出现时相同或不同并且选自:H,D,F,CN,Si(R3)4,具有1至10个碳原子的直链烷基基团,具有3至20个碳原子的支链或环状的烷基基团,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中所提及的烷基基团、所提及的芳族环系以及所提及的杂芳族环系各自被R3基团取代。
式(I)优选符合式(I-1)
其中出现的基团如上文定义的并且优选根据它们的优选实施方式定义,并且其中螺二芴上的未占据位置被R1基团取代。
式(II)优选符合式(II-1)
其中出现的基团如上文定义的并且优选根据它们的优选实施方式定义,并且其中芴上的未占据位置被R1基团取代。
式(I)的化合物的优选实施方式是WO2015/158411、WO2011/006574、WO2013/120577、WO2016/078738、WO2017/012687、WO2012/034627、WO2013/139431、WO2017/102063、WO2018/069167、WO2014/072017、WO2017/102064、WO2017/016632、WO2013/083216和WO2017/133829中作为示例结构引用的化合物。
式(II)的化合物的优选实施方式是WO2014/015937、WO2014/015938、WO2014/015935和WO2015/082056中作为示例结构引用的化合物。
以下,将空穴传输层中所述两种符合选自式(I)和(II)的相同或不同式的不同化合物中的一种称为HTM-1,而将空穴传输层中所述两种符合选自式(I)和(II)的相同或不同式的不同化合物中的另一种称为HTM-2。
在一个优选实施方式中,HTM-1符合选自式(I-1-A)和(II-1-A)的式
并且
HTM-2符合选自式(I-1-B)、(I-1-C)、(I-1-D)、(II-1-B)、(II-1-C)和(II-1-D)的式
其中在式(I-1-A)至(I-1-D)和(II-1-B)至(II-1-D)中出现的基团如上文定义的并且优选根据它们的优选实施方式定义,并且其中螺二芴和芴上的未占据位置各自被R1基团取代。更优选地,HTM-2符合式(I-1-B)或(I-1-D),最优选符合式(I-1-D)。在一个替代的优选实施方式中,HTM-2符合式(II-1-B)或(II-1-D),最优选符合式(II-1-D)。
优选地,HTM-1在空穴传输层中的存在比例高达所述层中HTM-2的比例的五至两倍。
优选地,HTM-1以50%-95%的比例,更优选以60%-90%的比例,最优选以65%-85%的比例存在于所述层中。
优选地,HTM-2以5%-50%的比例,更优选以10%-40%的比例,最优选以15%-35%的比例存在于所述层中。
优选地,HTM-1以65%-85%的比例存在于所述层中,HTM-2以15%-35%的比例存在于所述层中。
在一个优选实施方式中,HTM-1的HOMO为-4.8eV至-5.2eV,HTM-2的HOMO为-5.1eV至-5.4eV。更优选地,HTM-1的HOMO为-5.0eV至-5.2eV,HTM-2的HOMO为-5.1eV至-5.3eV。还优选HTM-1的HOMO高于HTM-2的。更优选地,HTM-1的HOMO比HTM-2的高0.02eV至0.3eV。“更高的HOMO”在此被理解为是指以eV计的值负性较小。
HOMO能级通过公开的说明书WO 2011/032624的第28页第1行至第29页第21行中描述的方法,用循环伏安法(CV)确定。
下表显示了化合物HTM-1的优选实施方式:
下表显示了化合物HTM-2的优选实施方式:
所述电子器件的空穴注入层优选直接邻接阳极。还优选它在阳极侧直接邻接空穴传输层。更优选地,所述电子器件具有阳极/空穴注入层/空穴传输层/发光层的层序列,其中所提及的层彼此直接邻接。
空穴注入层的厚度优选为2nm至50nm,更优选为2nm至30nm。其厚度优选不大于50nm,更优选不大于30nm。
在一个优选实施方式中,空穴注入层含有如上所述的p型掺杂剂和空穴传输材料的混合物。p型掺杂剂在此优选以1%至10%的比例存在于空穴注入层中。空穴传输材料在此优选选自本领域技术人员已知的用于OLED的空穴传输材料的材料类别,尤其是三芳基胺。特别优选的是茚并芴胺衍生物、胺衍生物、具有稠合芳族体系的胺衍生物、单苯并茚并芴胺、二苯并茚并芴胺、螺二芴胺、芴胺、螺二苯并吡喃胺、二氢吖啶衍生物、螺二苯并呋喃和螺二苯并噻吩、菲二芳基胺、螺三苯并托酚酮、具有间苯基二胺基团的螺二芴、螺双吖啶、呫吨二芳基胺和具有二芳基氨基基团的9,10-二氢蒽螺环化合物。
下表显示了用作空穴注入层中的空穴传输材料的优选具体化合物:
上述化合物H-1至H-146不仅适用于空穴注入层中,而且通常也适用于具有空穴传输功能的层,例如空穴注入层、空穴传输层和/或电子阻挡层中,或适合在发光层中用作基质材料,尤其是用作包含一种或多种磷光发光体的发光层中的基质材料。
化合物H-1至H-146通常对于在任何设计和组成的OLED中,而不是仅在本申请的OLED中的上述用途都具有良好的适合性。这些化合物在OLED中显示出良好的性能数据,尤其是良好的寿命和良好的效率。
空穴注入层的空穴传输材料更优选选自螺二芴基胺和芴基胺,更优选选自螺二芴基单胺和芴基单胺。单胺在此被理解为是指含有单个氨基基团的化合物。最优选地,空穴注入层的空穴传输材料选自以上定义的式(I-1-A)和(II-1-A)的化合物,更优选选自式(I-1-A)的化合物。
在一个替代的优选实施方式中,所述空穴注入层含有六氮杂联三苯叉衍生物,优选如US 2007/0092755中所述的,或其它高度缺电子和/或路易斯酸性的化合物,在每种情况下以纯形式存在,即不与其它化合物混合。这样的化合物的例子包括铋络合物,尤其是Bi(III)络合物,尤其是Bi(III)羧酸盐,例如上述化合物D-13。
除了阴极、阳极、发光层、空穴注入层和空穴传输层之外,所述电子器件优选还包含其它层。这些层优选在每种情况下选自一个或多个空穴阻挡层、电子传输层、电子注入层、激子阻挡层、中间层、电荷产生层和/或有机或无机层p/n结。然而,应该指出的是,这些层中的每一个不一定都需要存在。更特别地,优选所述电子器件包含一个或多个选自电子传输层和电子注入层的层,所述电子传输层和电子注入层布置在发光层和阳极之间。更优选地,所述电子器件在发光层和阴极之间依次包含一个或多个电子传输层、优选单一电子传输层和单一电子注入层,其中所提及的电子注入层优选直接邻接阴极。
所述电子器件中的层序列优选如下:
-阳极-
-空穴注入层-
-空穴传输层-
-发光层-
-任选的空穴阻挡层-
-电子传输层-
-电子注入层-
-阴极-。
用于所述电子器件的空穴阻挡层、电子传输层和电子注入层的合适的材料尤其是铝络合物,例如Alq3,锆络合物,例如Zrq4,锂络合物,例如Liq,苯并咪唑衍生物,三嗪衍生物,嘧啶衍生物,吡啶衍生物,吡嗪衍生物,喹喔啉衍生物,喹啉衍生物,二唑衍生物,芳族酮,内酰胺,硼烷,二氮杂磷杂环戊二烯衍生物,和氧化膦衍生物。下表显示了用于这些层的特定化合物的例子:
在一个优选实施方式中,所述电子器件特征在于通过升华工艺施加一个或多个层。在这种情况下,在真空升华***中在小于10-5毫巴,优选小于10-6毫巴的初始压力下通过气相沉积施加材料。然而,在这种情况下,所述初始压力也可以甚至更低,例如小于10-7毫巴。
同样优选的是如下所述的电子器件,其特征在于通过OVPD(有机气相沉积)法或借助于载气升华施加一个或多个层。在这种情况下,在10-5毫巴和1巴之间的压力下施加材料。该方法的特殊情况是OVJP(有机蒸气喷印)法,其中材料通过喷嘴直接施加并由此结构化(例如M.S.Arnold等,应用物理快报(Appl.Phys.Lett.)2008,92,053301)。
此外优选的是如下所述的电子器件,其特征在于从溶液中例如通过旋涂,或通过任何印刷方法例如丝网印刷、柔性版印刷、喷嘴印刷或胶版印刷,但更优选LITI(光引发热成像,热转印)或喷墨印刷,来产生一个或多个层。为此目的,需要可溶的化合物。高溶解度可以通过所述化合物的适当取代获得。
还优选通过从溶液中施加一个或多个层和通过升华法施加一个或多个层来制造本发明的电子器件。
在(根据用途)施加层之后,将器件结构化、设置接触连接并最终密封,以排除水和空气的破坏效应。
本发明的电子器件优选用于显示器中、用作照明应用中的光源或用作医学和/或美容应用中的光源。
实施例
1)OLED的通用制造方法和OLED的表征
涂有厚度为50nm的结构化ITO(氧化锡铟)的玻璃板是要施加OLED的基底。
OLED基本上具有以下层结构:基底/空穴注入层(HIL)/空穴传输层(HTL)/发光层(EML)/电子传输层(ETL)/电子注入层(EIL)以及最后是阴极。阴极由厚度为100nm的铝层形成。OLED的确切结构可以在表1中找到。
所有材料均在真空室中通过热气相沉积施加。在本实施例中,此处的发光层由基质材料(主体材料)和发光掺杂剂(发光体)组成,所述发光掺杂剂通过共蒸发以特定的体积比添加到所述基质材料中。以SMB1:SEB1(5%)这样的形式给出的细节在此意味着,材料SMB1以95%的体积比例以及材料SEB1以5%的体积比例存在于层中。类似地,电子传输层以及在特定实施例中的HIL和/或HTL也同样由两种材料的混合物组成,其中材料的比例如上文指定的那样报告。
用于OLED的材料的化学结构示于表2。
所述OLED以标准方式表征。为此目的,确定了电致发光光谱、外量子效率(EQE,以%计量)和寿命,所述外量子效率作为亮度的函数,由假定郎伯发光特征的电流-电压-亮度特性计算。参数EQE@10mA/cm2是指在10mA/cm2下达到的外量子效率。参数U@10mA/cm2是指在10mA/cm2下的工作电压。寿命LT被定义为在以恒流密度工作的过程中,亮度从起始亮度降至特定比例的时间。LT80数字在此意味着报告的寿命对应于亮度下降到其起始值的80%的时间。数字@60mA/cm2在此意味着所讨论的寿命是在60mA/cm2下测量的。
2)在HTL中用两种不同材料的混合物和在HTL中用单一材料的比较实施例与掺杂的HIL一起的OLED
制造了以下OLED:
这给出了以下测量数据:
通过将化合物HTM5添加到含有HTM3的HTL,在相同电压下,在OLED E1中获得了明显改善的效率。此处与OLED V1进行比较,OLED V1在HTL中仅含有化合物HTM3,其它方面构造相同。
当将化合物HTM6添加到含有HTM2的HTL时(OLED E2),也发现了效率的明显改善。此处与OLED V2进行比较,OLED V2在HTL中仅含有化合物HTM2,其它方面构造相同。
尽管效率的改善在百分比上小,但它们不可忽视,因为效率的改善很难实现。
3)在HTL中用两种不同材料的混合物和在HTL中用单一材料的比较实施例与由单一材料构成的HIL一起的OLED
制造了以下OLED:
这给出了以下测量数据:
通过将化合物HTM5(E3)或HTM6(E4)添加到含有化合物HTM1的HTL,在每种情况下都改善了寿命。此处与OLED V3进行比较,OLED V3在HTL中仅含有化合物HTM1,其它方面构造相同。
与OLED V3、E3和E4中使用的较厚HTL相比,在具有较薄HTL(70nm)的OLED的情况下,同样改善了寿命,如下面的实施例所示。和前面一样,在HTL中有两种不同材料的混合物的OLED(E6、E7和E8)在此与在HTL中仅含有化合物HTM1的OLED(V4)进行比较。
这给出了以下测量数据:
在所有情况下,添加选自HTM5、HTM6和HTM7的材料改善了OLED的寿命。
所述第二种材料也可按比上述20%更高的比例添加,如以下实施例所示:
得到以下结果:
然而,以高比例添加第二种材料具有发生效率损失的缺点。当第二种材料的使用比例为10体积%-30体积%,尤其是如上所示的20体积%时,即便有上述缺点,发生的程度也明显较低。
4)用于混合HTL中的化合物的HOMO的确定
在公开的说明书WO 2011/032624第28页第1行至第29页第21行描述的方法给出了化合物HTM1、HTM2、HTM3、HTM5、HTM6和HTM7的以下HOMO值:
化合物 | HOMO(eV) |
HTM1 | -5.15 |
HTM2 | -5.18 |
HTM3 | -5.15 |
HTM5 | -5.27 |
HTM6 | -5.23 |
HTM7 | -5.26 |
Claims (22)
1.一种电子器件,所述电子器件包含
-阳极,
-阴极,
-布置在阳极和阴极之间的发光层,
-布置在阳极和发光层之间的空穴注入层;
-布置在空穴注入层和发光层之间并且在阳极侧直接邻接发光层的空穴传输层,并且所述空穴传输层含有两种符合选自式(I)和(II)的相同或不同式的不同化合物
其中
X在每次出现时相同或不同并且选自单键、O、S、C(R1)2和NR1;
Ar1和Ar2在每次出现时相同或不同,并且选自具有6至40个芳族环原子并且被一个或多个R2基团取代的芳族环系以及具有5至40个芳族环原子并且被一个或多个R2基团取代的杂芳族环系;
R1和R2在每次出现时相同或不同并且选自:H,D,F,Cl,Br,I,C(=O)R3,CN,Si(R3)3,N(R3)2,P(=O)(R3)2,OR3,S(=O)R3,S(=O)2R3,具有1至20个碳原子的直链的烷基或烷氧基基团,具有3至20个碳原子的支链或环状的烷基或烷氧基基团,具有2至20个碳原子的烯基或炔基基团,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中两个或更多个R1或R2基团可彼此连接并且可形成环;其中所提及的烷基、烷氧基、烯基和炔基基团以及所提及的芳族环系和杂芳族环系各自被R3基团取代;并且其中所提及的烷基、烷氧基、烯基和炔基基团中的一个或多个CH2基团可被-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SO或SO2代替;
R3在每次出现时相同或不同并且选自:H,D,F,Cl,Br,I,CN,具有1至20个碳原子的烷基或烷氧基基团,具有2至20个碳原子的烯基或炔基基团,具有6至40个芳族环原子的芳族环系,以及具有5至40个芳族环原子的杂芳族环系;其中两个或更多个R3基团可彼此连接并且可形成环;并且其中所提及的烷基基团、烷氧基基团、烯基基团和炔基基团、芳族环系和杂芳族环系可被一个或多个选自F和CN的基团取代;
n是0、1、2、3或4,其中,当n=0时,Ar1基团不存在并且氮原子直接与式的其余部分键合。
2.根据权利要求1所述的电子器件,其特征在于所述发光层是发蓝色荧光的发光层或发绿色磷光的发光层。
3.根据权利要求1或2所述的电子器件,其特征在于所述空穴传输层的层厚度为20nm至300nm。
4.根据权利要求1至3中的一项或多项所述的电子器件,其特征在于所述空穴传输层的层厚度不大于250nm。
5.根据权利要求1至4中的一项或多项所述的电子器件,其特征在于所述空穴传输层含有正好两种符合选自式(I)和(II)的相同或不同式的不同化合物。
6.根据权利要求1至5中的一项或多项所述的电子器件,其特征在于所述空穴传输层由符合选自式(I)和(II)的相同或不同式的化合物组成。
7.根据权利要求1至6中的一项或多项所述的电子器件,其特征在于所述空穴传输层含有两种符合式(I)的不同化合物。
8.根据权利要求1至7中的一项或多项所述的电子器件,其特征在于所述两种符合选自式(I)和(II)的相同或不同式的不同化合物在所述空穴传输层中各自以至少5%的比例存在。
10.根据权利要求9所述的电子器件,其特征在于HTM-1在所述空穴传输层中的存在比例高达HTM-2在所述空穴传输层中的比例的五至二倍。
11.根据权利要求9或10所述的电子器件,其特征在于HTM-1以65%至85%的比例存在于所述空穴传输层中,并且HTM-2以15%至35%的比例存在于所述空穴传输层中。
12.根据权利要求9至11中的一项或多项所述的电子器件,其特征在于HTM-1的HOMO为-4.8eV至-5.2eV,并且HTM-2的HOMO为-5.1eV至-5.4eV。
13.根据权利要求9至12中的一项或多项所述的电子器件,其特征在于HTM-1的HOMO比HTM-2的高0.02eV至0.3eV。
14.根据权利要求1至13中的一项或多项所述的电子器件,其特征在于所述电子器件具有阳极/空穴注入层/空穴传输层/发光层的层序列,其中所提及的层彼此直接邻接。
15.根据权利要求1至14中的一项或多项所述的电子器件,其特征在于所述空穴注入层含有p型掺杂剂和空穴传输材料的混合物。
17.根据权利要求1至16中的一项或多项所述的电子器件,其特征在于所述空穴注入层含有各自以纯形式存在的六氮杂联三苯叉衍生物或其它高度缺电子和/或路易斯酸性的化合物。
18.一种用于制造根据权利要求1至17中的一项或多项所述的电子器件的方法,其特征在于从溶液中或通过升华工艺产生所述器件的一个或多个层。
19.根据权利要求1至17中的一项或多项所述的电子器件在显示器中、作为照明应用中的光源或作为医学和/或美容应用中的光源的用途。
21.根据权利要求20所述的化合物在有机电致发光器件中,优选在空穴传输层中和/或在发光层中作为基质材料的用途。
22.一种有机电致发光器件,所述有机电致发光器件含有根据权利要求20所述的化合物,优选在空穴注入层、空穴传输层、电子阻挡层和/或发光层中含有所述化合物。
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