TW202124366A - 用於有機電致發光裝置之材料 - Google Patents
用於有機電致發光裝置之材料 Download PDFInfo
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- TW202124366A TW202124366A TW109134170A TW109134170A TW202124366A TW 202124366 A TW202124366 A TW 202124366A TW 109134170 A TW109134170 A TW 109134170A TW 109134170 A TW109134170 A TW 109134170A TW 202124366 A TW202124366 A TW 202124366A
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- 239000000463 material Substances 0.000 title description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims description 78
- -1 N(R 1 ) 2 Inorganic materials 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 19
- 230000000903 blocking effect Effects 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 239000000412 dendrimer Substances 0.000 claims description 13
- 229920000736 dendritic polymer Polymers 0.000 claims description 13
- 238000005401 electroluminescence Methods 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 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 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000004020 luminiscence type Methods 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 238000006619 Stille reaction Methods 0.000 claims description 2
- 238000006887 Ullmann reaction Methods 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 238000006880 cross-coupling reaction Methods 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 1
- 125000006836 terphenylene group Chemical group 0.000 claims 1
- 239000011159 matrix material Substances 0.000 abstract description 9
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 2
- 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 abstract 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 95
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
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- 230000005525 hole transport Effects 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 125000005647 linker group Chemical group 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- 239000007787 solid Substances 0.000 description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 5
- 0 *c1cccc2c1-c1cc(-c3ccccc3*3c4ccccc4)c3cc1C2(N)N Chemical compound *c1cccc2c1-c1cc(-c3ccccc3*3c4ccccc4)c3cc1C2(N)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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 4
- 241001122767 Theaceae Species 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical class [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 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
- 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 2
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- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
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- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
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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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000000605 extraction Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
- C07D405/10—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 carbon chain containing aromatic rings
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- C07D405/14—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 three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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Abstract
一種茀衍生物,其於1-、1’-、4-或4’-位置中之一或多者以任何組合方式連接至二芳基取代之三
Description
本發明關於使用於電子裝置(特別是有機電致發光裝置)之材料,及包含此等材料之電子裝置,特別是有機電致發光裝置。
其中使用有機半導體作為功能材料的有機電致發光裝置(OLED)之結構係說明於例如US 4,539,507、US 5,151,629、EP 0676461和WO 98/27136中。在此所使用的發光材料越來越多為呈現磷光而不是螢光的有機金屬錯合物。為了量子力學的原因,使用有機金屬化合物作為磷光發光體,能量及功率效率可能增加高達四倍。然而,通常,在OLED的情況下,特別是亦在呈現三重態發光(磷光)之OLED的情況下,皆仍需要改良,例如關於效率、操作電壓及壽命。
磷光OLED之性質不只由所使用之三重態發光體決定。特別是,所使用的其他材料(諸如基質材料、電洞阻擋材料、電子傳輸材料、電洞傳輸材料和電子-或激子阻
擋材料)在此也特別重要。此等材料的改良因此也可導致OLED性質的顯著改良,特別是關於材料的效率,壽命和熱穩定性。
本發明之目的因此為提供適合使用於OLED(特別是作為用於磷光發光體之基質材料)之化合物,但亦用於作為電洞阻擋材料、作為電子傳輸材料或隨意地作為用於電荷產生層之材料。本發明之另一目的為提供其他用於有機電致發光裝置之有機半導體以便提供熟習該項技術者用於製造OLED的材料之更大可能的選擇。
已知具有非螺茀基和三基二者之化合物使用於OLED中。例如,US 7651790揭示具有式A-C-B之化合物的OLED之用途,其中A為電洞傳輸基(包括非螺茀基等等),B為電子傳輸基(包括三類等等)及C為一鍵或鍵聯基團。
US 6821643、US 6229012和US 6225467揭示於2-位置經三基取代之茀類。US 2004/0147742和Wu,Appl.Phys.Lett.,81(4),577-592揭示於2-位置經嘧啶類取代之茀類。
WO 2015/073343揭示具有經至少二個茀基(一為9,9-二苯基茀)取代之三化合物的OLED。顯示3-和4-三基
取代之茀類二者的實例。KR 2013115161揭示具有1-三基-9,9-二甲基茀之OLED,其中該三於係4-位置經1-苯并呋喃取代及於6-位置經N-茚衍生物取代。KR 2013061371揭示具有1-(4-苯基)三基-9,9-二甲基茀衍生物之OLED。
令人驚訝地,已發現:將於後文更詳細地描述的某些化合物達成這些目的,適合使用於OLED中且導致有機電致發光裝置之改良。改良在此特別是關於壽命及/或工作電壓。本發明因此關於這些化合物和電子裝置,特別是有機電致發光裝置,彼等包含下述類型的化合物。
Z1和Z2在每次出現時相同或不同地為H,D,F,Cl,Br,I,CHO,N(Ar1)2,C(=O)Ar1,P(=O)(Ar1)2,S(=O)Ar1,S(=O)2Ar1,CR2=CR2Ar1,CN,NO2,Si(R1)3,B(OR1)2,B(R1)2,B(N(R1)2)2,OSO2R1,具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkoxy)或具有2至40個C原子之直鏈烯基或炔基或具有3至40個C原子之支鏈或環狀烷基、烯基、炔基、烷氧基或烷硫基(彼等各自可經一或多個基團R1取代,其中一或多個較佳為非相鄰的CH2基團可經(R1)C=C(R1)、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=N(R1)、P(=O)(R1)、SO、SO2、N(R1)2、O、S或CON(R1)2置換及
其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換),或具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R1取代),或具有5至60個芳族環原子之芳氧基或雜芳氧基(其可經一或多個基團R1取代)。
本發明之茀衍生物不為雙-9,9’-螺聯茀類;也就是說,於9-位置之Z1和Z2基團不表示另一茀基團。因此,本發明的雜環取代之茀核不為下列之衍生物:
雖然雙-9,9-螺聯基團可為如下所述的其他取代基或鍵聯基團。應理解:在一些實施態樣中,Z1和Z2可形成螺飽和環系統;例如,Z1和Z2可表示環戊基或環己基環系統。然而,較佳的是Z1和Z2為彼此獨立的取代基且彼此不在茀核的9-位置以外的任何位置相連。
Y1和Y2在每次出現時相同或不同地為D,F,Cl,Br,I,CHO,N(Ar1)2,C(=O)Ar1,P(=O)(Ar1)2,S(=O)Ar1,S(=O)2Ar1,(R1)C=C(R1)Ar1,CN,NO2,Si(R1)3,B(OR1)2,B(R1)2,B(N(R1)2)2,OSO2R1,具有1至40個C原子之直鏈烷基、烷氧基或烷硫基或具有2至40個C原子之直鏈烯基或炔基或具有3至40個C原子之支鏈或環狀烷基、烯基、炔基、烷氧基或烷硫基(彼等各
自可經一或多個基團R1取代,其中一或多個較佳為非相鄰的CH2基團可經(R1)C=C(R1)、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=N(R1)2、P(=O(R1)2、SO、SO2、N(R1)2、O、S或CON(R1)2置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換),或具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R1取代),或具有5至60個芳族環原子之芳氧基或雜芳氧基(其可經一或多個基團R1取代),或此等系統的組合;二或多個相鄰的取代基Y1或Y2彼此也可形成稠合的單-或多環脂族或芳族或雜芳族環系統。
Ar1和Ar2在每次出現時相同或不同地為具有5至23個芳族環原子之芳族或雜芳族環系統(其可經一或多個基團R1較佳為非芳族基團R1取代),其先決條件為雜芳族環系統係經由碳-碳鍵連接;
R1在每次出現時相同或不同地選自由下列所組成之群組:H,D,F,Cl,Br,I,CN,Si(R2)3,具有1至40個C原子之直鏈烷基、烷氧基或烷硫基或具有3-40個C原子之支鏈或環狀烷基、烷氧基或烷硫基(其可經一或多個基團R2取代,其中一或多個非相鄰的CH2基團各自可經C(R2)=C(R2)、Si(R2)2、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2置換及其中一或多個H原子可經D、F、Cl、Br或I置換),具有6至40個碳原子的芳族或雜芳族環系統(其可經一或多個基團R2取代),具有5至
60個芳族環原子之芳氧基(其可經一或多個基團R2取代),或具有5至60個芳族環原子之芳烷基(其可經一或多個基團R2取代),其中隨意地二或多個相鄰的取代基R1可彼此形成單-或多環脂族、芳族或雜芳族環系統(其可經一或多個基團R2取代);其中R2係選自由下列所組成之群組:H、D、F、具有1至20個碳原子之脂族烴基或具有5至30個C原子之芳族或雜芳族環系統,其中二或多個相鄰的取代基R2可彼此形成單-或多環脂族、芳族或雜芳族環系統;
X在每次出現時相同或不同地為CR1或N,其先決條件為至少一個X表示N。
L在每次出現時相同或不同地為具有5-30個芳族環原子之芳族或雜芳族環系統,其可經一或多個非芳族基團R1取代。
a、b、c和d各自相同或不同地為0或1,其先決條件為a、b、c或d中之至少一者為1。
e和f各自相同或不同地為0、1、2或3。
n在每次出現時相同或不同地為0或1。
在本發明之一較佳實施態樣中,式(I)之化合物不為下列化合物:
除非另有指示,否則芳基在本發明的情況下含有從6至24個碳原子;雜芳基在本發明的意義範圍內含有從2至24個碳原子及至少一個雜原子,先決條件為碳原子及雜原子的總數為至少5。雜原子較佳係選自N、O及S。芳基或雜芳基之中為簡單芳族環(例如苯),或簡單雜芳族環(例如吡啶、嘧啶、噻吩、等等),或稠合芳基或雜芳基(諸如萘、蒽、菲、喹啉、異喹啉、等等)。
除非另有指示,否則芳族環系統就本發明之意義而言在環系統中含有從6至40個碳原子。除非另有指示,否則雜芳族環系統就本發明之意義而言在環系統中含有1至40個碳原子和至少一個雜原子,其先決條件為碳原子與雜原子之總和為至少5。雜原子較佳係選自N、O和S。除非另有指示,否則芳族或雜芳族環系統在本發明的情況下係理解為不一定只含有芳基或雜芳基,而是其中多個芳基或雜芳基可以非芳族部分(諸如,例如C、N或O原子或羰基)連接的系統。例如,除非另有指示,否則系統諸如9,9’-螺聯茀、9,9-二芳基茀、三芳基胺、二苯乙烯、等等為就本發明目的而言之芳族環系統。亦包括者為其中二或多個芳基例如以直鏈或環狀烷基或以矽基連接之系統。此外,除非另有指示,否則其中二或多個芳基或雜芳基係彼此直接連結之系統(諸如,例如聯苯、聯三苯、或聯四苯)也理解為芳族或雜芳族環系統。
就本發明之目的而言,環狀烷基、烷氧基或烷硫基意指單環、雙環或多環基團。
在本發明中,C1至C40烷基(其中個別H原子或CH2基團可經上述基團取代)包括甲基、乙基、正丙基、異丙基、環丙基、正丁基、異丁基、第二丁基、第三丁基、環丁基、2-甲基丁基、正戊基、第二戊基、第三戊基、2-戊基、新戊基、環戊基、正己基、第二己基、第三己基、2-己基、3-己基、新己基、環己基、1-甲基環戊基、2-甲基戊基、正庚基、2-庚基、3-庚基、4-庚基、環庚基、1-甲基環己基、正辛基、2-乙基己基、環辛基、1-雙環[2.2.2]辛基、2-雙環[2.2.2]辛基、2-(2,6-二甲基)辛基、3-(3,7-二甲基)辛基、金剛烷基、三氟甲基、五氟乙基、2,2,2-三氟乙基、1,1-二甲基-正己-1-基、1,1-二甲基-正庚-1-基、1,1-二甲基-正辛-1-基、1,1-二甲基-正癸-1-基、1,1-二甲基-正十二-1-基、1,1-二甲基-正十四-1-基、1,1-二甲基-正十六-1-基、1,1-二甲基-正十八-1-基、1,1-二乙基-正己-1-基、1,1-二乙基-正庚-1-基、1,1-二乙基-正辛-1-基、1,1-二乙基-正癸-1-基、1,1-二乙基-正十二-1-基、1,1-二乙基-正十四-1-基、1,1-二乙基-正十六-1-基、1,1-二乙基-正十八-1-基、1-(正丙基)環己-1-基、1-(正丁基)環己-1-基、1-(正己基)環己-1-基、1-(正辛基)環己-1-基及1-(正癸基)環己-1-基。烯基的實例包括乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基或環辛二烯基。炔基的實例包括(例如)乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。具有1至40個C原子之烷氧基較佳意指甲
氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、正戊氧基、第二戊氧基、2-甲基丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。具有1至40個C原子之烷硫基(thioalkyl)特別是意指甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、第二丁硫基、第三丁硫基、正戊硫基、第二戊硫基、正己硫基、環己硫基、正庚硫基、環庚硫基、正辛硫基、環辛硫基、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、環戊烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、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。通常,根據本發明之烷基、烷氧基或烷硫基可為直鏈、支鏈或環狀,其中一或多個非相鄰的CH2基團可經上述基團置換;再者,一或多個H原子亦可經D、F、Cl、Br、I、CN或NO2,較佳F、Cl或CN,進一步較佳F或CN,特佳CN置換。
除非另有指示,否則可經上述殘基取代且可經由芳族或雜芳族化合物上之任何位置鍵聯的具有5-60個芳族環原子之芳族或雜芳族環系統,例如,基團係理解為衍生自:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、(chrysene)、苝、丙二烯合茀(fluoranthene)、苯并丙二烯合茀(benzfluoranthen)、稠四苯、稠五苯、苯并芘、聯
苯、聯苯、聯三苯(terphenyl)、茀、螺聯茀、二氫菲、二氫芘、四氫芘、順-或反-茚并茀、順-或反-單苯并茚并茀、順-或反-二苯并茚并茀、三聚茚(truxene)、異三聚茚(isotruxene)、螺三聚茚、螺異三聚茚、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吲哚并咔唑、茚并咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻(phenothiazine)、啡噁、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑(naphthimidazole)、菲并咪唑(phenanthrimidazole)、吡啶并咪唑(pyridimidazole)、吡并咪唑(pyrazinimidazole)、喹噁啉并咪唑(chinoxalinimidazole)、噁唑、苯并噁唑、萘并噁唑(naphthoxazole)、蒽并噁唑(anthroxazole)、菲并噁唑(phenanthroxazole)、異噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒、苯并嗒、嘧啶、苯并嘧啶、喹噁啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮芘、4,5-二氮芘、4,5,9,10-四氮雜苝、吡、啡、啡噁、啡噻、螢紅環(fluorubin)、啶、氮雜咔唑、苯并咔啉(benzocarboline)、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、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、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌
呤、喋啶、吲和苯并噻二唑。
在上述中,R1係指第一取代基,及R2為在R1上以及在L、Z1、Z2、Y1和Y2上之其他隨意的取代基。R1和R2兩者皆可獨立地選自如所述的相同基團。相鄰基團或相鄰取代基就在本申請的意義而言意指鍵結至C原子上的取代基,彼等轉而與彼此或鍵結至相同C原子的取代基直接鍵結。
在藉由真空蒸發處理的化合物中,烷基較佳具有不超過5個C原子,特佳不超過4個C原子,非常特佳不超過1個C原子。對於從溶液處理的化合物,適當化合物也為彼等經具有至多10個C原子之烷基(特別是支鏈烷基)取代者,或經由寡聚伸芳基(例如鄰-、間-、對-或支鏈聯三苯基團)取代者。應理解:對於藉由真空沈積處理的化合物,可同時共蒸發多於一種化合物以形成混合層。例如,二或多種不同主體化合物(一者是根據本發明之化合物)的混合物可以預定比例混合,且然後將固體混合物共同蒸發以形成混合基質層(具有發光材料)。或者,可分別蒸發二種(或多種)化合物,並將所得蒸氣以適當的比例混合以形成混合層。
若式(I)或較佳實施態樣之化合物係用作磷光發光體之基質材料或使用於與磷光層直接相鄰之層中,則進一步更佳的是化合物之R1、R2、Z1、Z2、Y1、Y2、Ar1和Ar2及L不含其中超過二個的六員環彼此直接縮合的縮合芳基或雜芳基。然而,一個例外為聯伸三苯基團,其具有二個以
上的稠合六員環,但仍然適合具佳作為三重態基質材料。通常有利的是:用作基質材料或用於相鄰層中的化合物之三重態能量與發光層中的磷光材料的三重態能量相同或更大。
可使用上述根據本發明之化合物,特別是經反應性脫離基(諸如溴、碘、氯、硼酸或硼酸酯)或經反應性可聚合基團(諸如烯烴類、苯乙烯類、丙烯酸酯類或氧呾類)取代之化合物作為用於產生對應寡聚物、樹枝狀聚合物或聚合物的單體。寡聚合或聚合在此較佳經由鹵素官能性或硼酸官能性或經由可聚合基團進行。此外可能經由此類型的基團交聯聚合物。根據本發明之化合物和聚合物可用作交聯或未交聯層。
本發明因此另外關於含有一或多種上示根據本發明之化合物的寡聚物、聚合物或樹枝狀聚合物,其中從根據本發明之化合物至該聚合物、寡聚物或樹枝狀聚合物之一或多個鍵而非取代基存在於一或多個位置上。取決於根據本發明之化合物的鍵聯,此形成寡聚物或聚合物之側鏈或係鍵聯於主鏈中或形成樹枝狀聚合物之核心。聚合物、寡聚物或樹枝狀聚合物可為共軛、部分共軛或非共軛。寡聚物或聚合物可為直鏈、支鏈或樹枝狀。如上所述之相同的較佳選擇適用於寡聚物、樹枝狀聚合物及聚合物中的根據本發明之化合物的重複單元。
為了製備寡聚物或聚合物,將根據本發明之單體進行均聚合或與其他單體進行共聚合。較佳者為均聚物或共聚
物,其中上述式(I)或較佳實施態樣之單元係以0.01至99.9mol%,較佳為5至90mol%,特佳為20至80mol%之範圍存在。形成聚合物骨架之適合且較佳的共聚單體係選自茀類(例如根據EP 842208或WO 2000/22026)、螺聯茀類(例如根據EP 707020、EP 894107或WO 2006/061181)、對伸苯基類(例如根據WO 92/18552)、咔唑類(例如根據WO 2004/070772或WO 2004/113468)、噻吩類(例如根據EP 1028136)、二氫菲類(例如根據WO 2005/014689)、順-和反-茚并茀類(例如根據WO 2004/041901或WO 2004/113412)、酮類(例如根據WO 2005/040302)、菲類(例如根據WO 2005/104264或WO 2007/017066)亦或多個此等單元。聚合物、寡聚物及樹枝狀聚合物也可含有其他單元,例如電子傳輸單元。此外,聚合物可含有三重態發光體,其共聚或混合成摻合物。特別地,根據本發明之寡聚物、聚合物或樹枝狀聚合物與三重態發光體的組合導致特別好的結果。
較佳的是在茀核之9-位置中的Z1和Z2基團相同或不同地為具有1至12個原子之直鏈或支鏈烷基,或具有5
至40個芳族環原子之芳族或雜芳族環系統。更佳為其中Z1和Z2相同或不同地為具有1至6個原子之直鏈烷基,或具有6至24個芳族環原子之芳族環系統。烷基的特佳實例包括甲基和乙基。芳族環系統的特佳實例為苯基、對-第三-丁基苯基、對-(雜芳族)苯基、間-或對-聯苯或萘基。這些之中,最佳的是甲基或苯基。而Z1和Z2基團可為相同或不同,更佳的是彼等為相同。本發明化合物的茀核上之適當Z1和Z2取代基的一些具體實例包括,但不限於:
Y1和Y2表示在本發明化合物的茀核的兩個不同環上之取代基。應理解每當a、b、c或d為0時(沒有Q基團),彼等位置可或不可被Y1或Y2基團佔據。每當e或f為0時,沒有Y1或Y2取代基在該環上且開放位置為H。此為最佳的。每當e或f不為0時,Y1和Y2相同或不同
地為具有5至60個芳族環原子之較佳芳族或雜芳族環系統。較佳芳族基團的一些實例包括經取代或未經取代之苯基、萘基、或蒽基,彼等各自可經一或多個R1基團進一步取代。較佳雜芳族基團的一些實例包括N-芳基咔唑類、苯并咪唑類、二苯并呋喃類、二苯并噻吩類或茀類,包括9,9’-螺聯茀類。每當e或f為2時,此外較佳是二個相鄰的Y1或Y2取代基彼此形成稠合單-或多環脂族或芳族或雜芳族環系統。本發明化合物的茀核上之適當Y1和Y2取代基的一些實例包括,但不限於:
在上述結構中,R1如上述所定義且g可獨立地為0、1、2、3或4。
相鄰且一起形成稠合環系統之適當Y1和Y2的下列實例,其中在式(I)化合物中,a、b、c和d中只有一者為1且其他為0。應理解:這些說明性實例不是限制性的,且其中a、b、c或d以任何組合方式為0或1之類似實例也是可能的。
在本發明之化合物中,茀核以任何組合方式在1-、1’-、4-、4’-位置經一至四個Q基團取代。較佳的是a或b中只有一者為1而c或d中只有一者為1。甚至更佳的是:若b為1(a為0)而c或d為1。又甚至更佳的是:a或b中只有一者為1而c和d兩者皆為0。最佳的是:只有b為1而a、c和d為0。
L為將三或嘧啶基團中之碳原子連接(直接或間接)至茀核的鍵聯基團。當n為0時,沒有鍵聯基團且三或嘧啶基團之碳原子在1-、1’-、4-或4’-位置以單鍵直接連接至茀核。例如,若a、b、c和d各自為1且各者對應n為0,則式(I)化合物將為:
可理解的是:對於各Q基團而言,n可為相同或不同。例如,在其中b和d兩者皆為1(a和c為0)的情況下,對應n可為0和1,如下所示:
當n為1時,L為經由至少一個不是三/嘧啶基團或茀核的一部分之其他原子將三或嘧啶基團中之碳原子間接連接至茀核的1-、1’-、4-或4’-位置中之任一者的鍵聯基團。三/嘧啶連接至L以及L連接茀核皆為經由單鍵。較佳地,L在每次出現時相同或不同地為具有6-30個芳族環原子之芳族環系統,其可進一步經取代。較佳L基團的一些實例為苯基、聯苯或蒽基。此等之中,苯基為最佳,希望經由苯基的1,4-或1,3-位置。應理解:對於各Q基團,L可為相同或不同;例如,在下列化合物中,其中b和d為1(a和c為0),對應L基團為不同:
最佳的是:n為0。
在式(I)中,至少一個X在每次出現時相同或不同表示N。就本發明的意義而言,此意指就各Q基團而言,在各雜芳族環中至少一個X為N。當單環中的二個X皆為N時,其為較佳,Q基團為2,4-二取代之1,3,5-三(三基):
當只有一個X為N且另一個X為CR1時,Q基團為2,4-二取代之1,5-或1,3-嘧啶(嘧啶基)基團:
在這些嘧啶基團任一者中,較佳的是存在於X上之基團R1不與任何相鄰取代基(Ar1、Ar2、L或若n為0,茀核或任何Y取代基)形成環。特別是,較佳的是:三基或嘧啶基為單環系統且沒有稠合環。最佳的是:R1為H。
應理解:X的選擇在各Q基團內是獨立的。也就是說,式(I)化合物可具有1至4個三基,1至4個嘧啶基或1至4個於任何二個之組合之基團。例如,下列式(I)化合物,其中二個Q之基團b和d皆為1且a和c為0和n為0說明Q可為相同或混合:
上述示例性實例不是限制性的,且其中在4-和1’-位置處的基團互換,或者位於1-和4’-、1-和4-、1’-和4’-位置之類似實例也是可能的。也可預見具有3個或4個由三基或嘧啶基之相同或任何組合的混合物組成之Q基團的實例。
在三基或嘧啶基Q的情況下,較佳基團Ar1和Ar2為相同或獨立地為具有5至23個芳族環原子之芳族或雜芳族環系統,其在各情況下可經一或多個基團R1取代。
芳族環原子(碳或雜原子)的總數為在包括R1(若存在)的取代基中的所有芳族基團內之所有各個芳族環原子的總數(其包括為此目的之所有sp2混成碳原子和當雜原子連接至至少二個不同sp2碳原子時的二價和三價雜原子,但不包括非芳族四面體碳和氮原子)。例如,Ar1和Ar2的適合基團(與彼等的芳族環原子總數)包括苯(6),鄰-、間-或對-聯苯(12),鄰-、間-、對-或支鏈聯三苯(18),1-、2-、3-或4-9,9-二烷基茀基(12),1-或2-萘基(10),吡咯(5),呋喃(5),噻吩(5),吲哚(9),苯并呋喃(9),苯并噻吩(9),1-、2-或3-N-烷基咔唑(13),1-、2-或3-N-苯基咔唑(19),其也經由N-苯基連接,1-、2-或3-二苯并呋喃(13),1-、2-或3-二苯并噻吩(13),茚并咔唑(19),吲哚并咔唑(20),2-、3-或4-吡啶(6),2-、4-或5-嘧啶(6),吡(6),嗒(6),三(6),蒽(14),菲(14),聯伸三苯(18),芘(16),苯并蒽(18),N-苯基啡啶酮(20)或此等基團之二或三個之組合,彼等各自可經一或多個基團R1取代,只要總共不超過23個芳族環原子即可。具有大於23個芳族環原子之非發明取代基的一些實例為聯四苯(24),9,9-二苯基茀(24)和9,9’-螺聯茀(24)。Ar1和Ar2特別是選自由下列所組成之群組:苯、鄰-、間-或對-聯苯、鄰-、間-、對-或支鏈聯三苯,萘基,聯伸三苯,9,9-二烷基茀基或衍生物,N-苯基咔唑,二苯并呋喃和二苯并噻吩。應理解:此較佳基團不僅包括基本未經取代之結構,且也包括其衍生物,諸如彼等經其他R1取代基取代者。特別地,9,9-二烷
基茀基、N-苯基咔唑、二苯并呋喃和二苯并噻吩衍生物可具有稠合環經由鍵聯苯基連接至Q,只要在包括R1中的任何芳族環原子之整個取代基中有23個或更少的芳族環原子。較佳的是Ar1和Ar2上之任何R1取代基為非芳族。Ar1和Ar2經由一個單鍵連接至三基或嘧啶基且不形成環系統或具有任何至三基或嘧啶基之其他連接。而且,Ar1和Ar2係與鍵聯基團L不同;也就是說,三基或嘧啶基不經由Ar1或Ar2連接到茀。在本發明之一較佳實施態樣中,Ar1和Ar2為相同。
在本發明之另一較佳實施態樣中,基團Ar1和Ar2中之芳族基團,若任一個含有多於一個芳基,則不為對-鍵聯,即彼等較佳不為對-聯苯基或對-聯三苯基,而是例如個別鄰-或間-鍵聯結構。
然而,若Ar1或Ar2(或二者)為或含有含氮之雜芳族基團諸如咔唑、吡咯、咪唑或苯并咪唑基團,則雜芳族基團不經由氮原子而直接鍵聯至三或嘧啶核,而是經由雜芳族基團的碳原子鍵聯至三或嘧啶中的碳原子。例如,若Ar1或Ar2為N-苯基咔唑基團,則其可經由咔唑的碳原子或N-苯基的碳原子連接至三或嘧啶核(如下述實例所示),但若Ar1或Ar2為咔唑基團,則其應不連接至三或嘧啶核而直接以咔唑基團之氮原子。
Ar1和Ar2的一些非限制例包括:
如上所述,在式(I)化合物中較佳的是:Z1和Z2為相同。此對應於式II:
如上所述,在式(I)化合物中較佳的是:e或f兩者皆為0,所以沒有Y1或Y2取代基且開放位置為H。此對應於式(III):
如上所述,在式(I)化合物中,較佳的是:a或b中只有一者為1而c或d中只有一者為1。此等對應於式(IV)和(V):
如上所述,在式(I)化合物中較佳的是:b為1,a為0而c或d為1而其他為0。此對應於式(VI)和(VII):
如上所述,在式(I)化合物中較佳的是:b為1而a、c和d為0。此對應於式(VIIIa):
或者,在式(I)化合物中較佳的是:a為1,而b,c和d為0。此對應於式(VIIIb):
上述較佳實施態樣可根據需要彼此組合。在本發明之一特佳實施態樣中,上述較佳選擇同時發生。例如,下式(IX)至(XVII)包括一些特徵的較佳組合,其中Q係位於4-位置:
也預想到式(IX)至(XVII)的類似化合物,其中Q係位於1-位置而不是4-位置。此等之中,最佳的是式XII、XV、XVI和XVII,其中二個X皆為氮以形成三基(或對
應化合物,其中三基於1-位置)。
下列實例代表一些根據式(I)化合物:
為了從液相處理根據本發明之化合物(例如藉由旋塗或藉由印刷方法),根據本發明之化合物的調配物為必需。此等調配物可為例如溶液、分散液或乳液。為此目
的,較佳可為使用二或多種溶劑之混合物。適當且較佳的溶劑為(例如)甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、均三甲苯、四氫萘、藜蘆醚、THF、甲基-THF、THP、氯苯、二噁烷、苯氧基甲苯(特別是3-苯氧基甲苯)、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯啶酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、異丙苯、環己醇、環己酮、環己基苯、十氫萘、十二烷基苯、苯甲酸乙酯、茚烷、六甲基茚烷、苯甲酸甲酯、NMP、對-異丙基甲苯、苯基乙基醚、1,4-二異丙基苯、二苯甲基醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇單丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-異丙基萘、戊基苯、己基苯、庚基苯、辛基苯、1,1-雙(3,4-二甲基苯基)乙烷或此等溶劑之混合物。
本發明因此進一步關於一種調配物,其包含根據本發明之化合物和至少一種其他化合物。其他化合物可為(例如)溶劑,特別是上述溶劑中之一者或此等溶劑之混合物。然而,其他化合物也可為至少一種同樣可用於電子裝置之其他有機或無機化合物,例如發光化合物及/或其他基質材料。適當發光化合物和其他基質材料為如下所示與有機電致發光裝置有關者。此其他化合物也可為聚合的。
根據本發明化合物係適合使用於電子裝置中,特別是
使用於有機電致發光裝置中。本發明因此另外關於根據本發明之化合物於電子裝置(特別是於有機電致發光裝置)之用途。本發明仍進一步關於一種包含至少一種根據本發明化合物之電子裝置。
電子裝置就本發明之意義而言為包含至少一個包含至少一種有機化合物之層的裝置。該組件亦可包含無機材料或完全由無機材料構建之層。電子裝置較佳係選自由下列所組成之群組:有機電致發光裝置(OLED)、有機積體電路(O-IC)、有機場效電晶體(O-FET)、有機薄膜電晶體(O-TFT)、有機發光電晶體(O-LET)、有機太陽能電池(O-SC)、染料敏化之有機太陽能電池(DSSC)、有機光學檢測器、有機感光器(photoreceptor)、有機場淬滅裝置(O-FQD)、發光電化學電池(LEC)、有機雷射二極體(O-雷射)和“有機電漿子發射裝置(organic plasmon emitting device)”,但較佳為有機電致發光裝置(OLED),特佳為磷光OLED。
有機電致發光裝置包含陰極、陽極及至少一個發光層。除了此等層以外,有機電致發光裝置亦可包含其他層,例如在各情況下一或多個電洞注入層、電洞傳輸層、電洞阻擋層、電子傳輸層、電子注入層、激子阻擋層、電子阻擋層、及/或電荷產生層。同樣可在二個發光層之間引入具有(例如)激子阻擋功能之中間層。然而,應指出的是此等層之各者不一定必須存在。有機電發致光裝置在此可包含一個發光層,或其可包含多個發光層。若存在多個
發光層,則此等較佳地具有總計多個在380奈米與750奈米之間的發光最大值,導致整體白色發光,亦即將能夠發螢光或磷光的各種發光化合物使用於發光層中。特佳者為具有二個發光層之系統,其中該二層呈現藍色及橙色或黃色發光,或具有三個發光層之系統,其中該三層呈現藍色、綠色及橙色或紅色發光(基本結構參見例如WO 2005/011013)。根據本發明之有機電致發光裝置也可為串聯式OLED,特別是也用於白色發光OLED。
根據上示實施態樣的根據本發明之化合物可使用於電子裝置的各種層中,取決於精確結構。較佳者為一種有機電致發光裝置,其包含式(I)或上示較佳實施態樣之化合物作為用於磷光或螢光發光體(特別是用於磷光發光體)之基質材料、及/或用於電子阻擋或激子阻擋層及/或電荷產生層及/或電洞阻擋或電子傳輸層中,取決於精確取代。
在本發明之一較佳實施態樣中,根據本發明之化合物用作發光層中的磷光化合物之基質材料。有機電致發光裝置在此可包含一個發光層,或其可包含多個發光層,其中至少一個發光層包含至少一種根據本發明之化合物作為基質材料。
若根據本發明之化合物用作發光層中的磷光化合物之基質材料,則較佳的是與一或多種磷光材料(三激態發光體)組合使用。磷光就本發明的意義而言意指從具有較高自旋多重性(即,自旋態>1)的激發態(特別是從激發三重態)之發光。就本申請案的意義而言,所有含有過渡金屬或鑭
系元素之發光錯合物(特別是所有銥、鉑和銅錯合物)係視為磷光化合物。
根據本發明之化合物和發光化合物的混合物以包含發光體和基質材料的整個混合物為基準計,包含介於99和1體積%之間,較佳介於98和10體積%之間,特佳介於97和60體積%之間,特別是介於95和80體積%之間的根據本發明之化合物。對應地,混合物以發光體和基質材料的整個混合物為基準計,包含介於1和99體積%,較佳地介於2和90體積%之間,特佳地介於3和40體積%之間,特別是介於5和20體積%之間的發光體。本發明之另一較佳實施態樣為根據本發明之化合物與其他基質材料組合作為磷光發光體之基質材料的用途。可與根據本發明之化合物組合使用之特別適合的基質材料為芳族酮、芳族氧化膦或芳族亞碸或碸(例如,根據WO 2004/013080、WO 2004/093207、WO 2006/005627或WO 2010/006680)、三芳基胺、咔唑衍生物(例如CBP(N,N-雙咔唑基聯苯)或WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527、WO 2008/086851或WO 2013/041176中所揭示之咔唑衍生物)、吲哚并咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、茚并咔唑衍生物(例如,根據WO 2010/136109、WO 2011/000455、WO 2013/041176或WO 2013/056776)、氮雜咔唑衍生物(例如,根據EP 1617710、EP 1617711、EP 1731584、JP 2005/347160)、雙極性基質材料(例如根據
WO 2007/137725)、矽烷(例如根據WO 2005/111172)、氮硼雜環戊烯(azaborole)或硼酸酯(例如根據WO 2006/117052)、三衍生物(例如根據WO 2007/063754、WO 2008/056746、WO 2010/015306、WO 2011/057706、WO 2011/060859或WO 2011/060877)、鋅錯合物(例如根據EP 652273或WO 2009/062578)、二氮雜矽雜環戊二烯(diazasilole)或四氮雜矽雜環戊二烯衍生物(例如根據WO 2010/054729)、二氮磷雜環戊二烯(diazaphosphole)衍生物(例如根據WO 2010/054730)、橋聯咔唑衍生物(例如根據WO 2011/042107、WO 2011/060867、WO 2011/088877和WO 2012/143080)、或聯伸三苯衍生物(例如,根據WO 2012/048781)。在比實際發光體短的波長發光之其他磷光發光體同樣可存在於混合物中作為共主體,如果有的話,不參與電荷傳輸至顯著程度的化合物,如例如WO 2010/108579中所述。選擇用於光發射層的適當基質材料和發光體以及確定所存在之所有材料的適當相對比例係在該項技術範圍內。
適當磷光化合物(=三重態發光體)特別為在適當激發時發光(較佳在可見光區域)且另外含有至少一種具有原子序大於20,較佳為大於38且少於84,特佳為大於56且少於80的原子之化合物,特別是具有此原子序的金屬。所使用之磷光發光體較佳為含有銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪的化合物,特別是含有銥或鉑的化合物。
上述發光體的實例係由申請案WO 00/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 2005/033244、WO 2005/019373、US 2005/0258742、WO 2010/086089、WO 2011/157339、WO 2012/007086、WO 2012/163471、WO 2013/000531、WO 2013/020631、WO 2014/008982和WO 2014/023377揭示。通常,根據先前技術用於磷光OLED且為熟習有機電致發光裝置領域之技術者已知的所有磷光錯合物皆適合,且熟習該項技術者也將能夠在無進步性下使用其他磷光錯合物。
根據本發明之化合物亦(特別地)適合作為有機電致發光裝置中之磷光發光體的基質材料,如例如US 2011/0248247和US 2012/0223633中所述。在此等多色顯示器組件中,額外藍色發光層係藉由蒸氣沈積在整個區域上而施加至所有像素(以及彼等具有非藍色者)上。在此令人訝異地已發現:根據本發明之化合物,當用作紅及/或綠像素的基質材料時,持續與蒸氣沈積的藍色光射層一起產生極佳發光。
在本發明另一實施態樣中,根據本發明的有機電致發光裝置不包含單獨的電洞注入層及/或電洞傳輸層及/或電洞阻擋層及/或電子傳輸層,亦即發光層直接與電洞注入層或陽極相鄰,及/或發光層直接與電子傳輸層或電子注入層或陰極相鄰,如例如在WO 2005/053051中所述。此外可能使用與發光層中之金屬錯合物相同或類似的金屬錯
合物作為直接與發光層相鄰之電洞傳輸或電洞注入材料,如例如WO 2009/030981中所述。
在本發明另一實施態樣中,根據本發明之化合物係使用於激子阻擋層中。
在本發明之又另一較佳實施態樣中,根據本發明之化合物係用作電子傳輸或電子注入層中之電子傳輸材料。發光層在此可為螢光或磷光。若化合物係用作電子傳輸材料,則其較佳可經例如鹼金屬或鹼金屬錯合物(諸如,例如,Li或LiQ(羥基喹啉鋰)摻雜。
在本發明之又另一較佳實施態樣中,根據本發明之化合物係使用於電洞阻擋層中。電洞阻擋層意指與陰極側上的發光層直接相鄰之層。另一較佳實施態樣係使用該化合物作為電荷產生層之部分。電荷產生層(CGL)在施加電壓時充當電子-電洞對的注入器並且是該技項技術所熟知的。通常,CGL由與缺電子層(例如,p-摻雜的電洞傳輸層)相鄰的富電子層(例如,n-摻雜的電子傳輸層)組成。然而,在一些情況下,CGL可僅為單層。在其他情況下,CGL之一或二層可或可不經摻雜。
在根據本發明之有機電致發光裝置的其他層中,可使用根據先前技術通常使用之所有材料。熟習該項技術者因此將能夠在無進步性下使用已知用於有機電致發光裝置之所有材料與根據本發明或上述較佳實施態樣之式(I)化合物的組合。
此外較佳者為有機電致發光裝置,其特徵在於利用昇
華方法施加一或多層,其中該等材料係於真空昇華單元中在低於10-5毫巴,較佳低於10-6毫巴之初壓力下藉由蒸氣沈積施加。然而,初壓力也可能甚至更低,例如低於10-7毫巴。
同樣較佳者為一種有機電致發光裝置,其特徵在於利用OVPD(有機蒸氣相沈積)法或輔以載體-氣體昇華法施加一或多層,其中該等材料係在介於10-5毫巴與1巴之間的壓力下施加。此方法的一特殊實例為OVJP(有機蒸氣噴墨印刷)方法,其中該等材料係經由噴嘴直接施加且因此結構化(例如,M.S.Arnold等人之Appl.Phys.Lett.2008,92,053301)。
此外較佳者為一種有機電致發光裝置,其特徵在於諸如(例如)以旋轉塗佈或利用任何所需印刷方法(諸如,例如網版印刷、快乾印刷、平版印刷、LITI(光誘導熱成像、熱轉移印刷)、噴墨印刷或噴嘴印刷)從溶液製造一或多層。為此目的需要可溶性化合物,其可(例如)藉由適當取代而獲得。
亦可能者為混雜方法,其中(例如)從溶液施加一或多層及以蒸氣沈積施加一或多層。這些方法通常為熟習該項技術者已知的且可由其在沒有進步性下應用於包含根據本發明之化合物的有機電致發光裝置中。
根據本發明之化合物和根據本發明之有機電致發光裝置以下列超越先前技術之令人驚訝的優點之一或多者為特徵:
1.根據本發明之化合物,用作螢光或磷光發光體之基質材料,導致長壽命。特別地,若化合物用作磷光發光體的基質材料,則此適用。
2.根據本發明之化合物導致非常高的效率。特別地,若化合物用作磷光發光體的基質材料或作為電洞阻擋材料,則此適用。
3.在一些實施態樣中,根據本發明之化合物導致低電壓裝置。特別地,若化合物用作磷光發光體的基質材料或用於電子傳輸層中,則此適用。
上述這些優點不伴隨其他電子性質的損害。
本發明係以下列實施例更詳細地說明,不希望本發明因而受到限制。熟習該項技術者將能夠在沒有進步性下使用該說明來進行所揭示的整個範圍內之本發明及製備其他根據本發明之化合物並將彼等使用於電子裝置或應用根據本發明之方法。
實施例
合成例
除非另有指示,否則在保護性氣體氛圍下在乾燥溶劑中進行下列合成。溶劑和試劑可自ALDRICH或ABCR購買。在市售起始材料之情況中所指示的編號係對應於CAS編號。
本發明之材料通常可根據下列合成流程圖1製備(注
意:在流程圖1中,二或三個X將為N及當有二個氮時,另一個X將為CR1和R3較佳為(但不限於)茀骨架;在一些實施態樣中,可在步驟1或2a/b中添加茀骨架):
步驟1:在四頸燒瓶中在惰性氛圍下將295g(1.6mol,1.0eq)的2,4,6-三氯-1,3,5-三[108-77-0]1溶解在800ml乾燥THF中。用冰浴將溶液冷卻至約0℃並緩慢添加800ml(1.6mol,1.0eq)的2mol/l氯化苯鎂溶液以保持溫度低於10℃。接著,將混合物在室溫下攪拌過夜並在反應完成後,添加800ml的甲苯和1.2L的HCl 2%。分離有機相,用水萃取三次和經過硫酸鈉乾燥。在減壓下蒸發溶劑,直至產物沈澱。用乙醇洗滌固體後,獲得242g(1.1mol,67%)的所要產物3a。
類似地獲得其他實施例:
步驟2a:將1.5g(61mmol,1.12eq)的鎂屑在四頸燒瓶中加熱幾分鐘。接著,添加幾ml的在100ml乾燥THF中之19g(60mmol,1.10eq)的1-溴-3,5-二苯基苯[103068-20-8]直到格任亞(Grignard)反應開始。接著,緩慢添加溶液以將格任亞反應維持在回流下。添加完成後,用冰浴冷將混合物卻至約0℃。在第二裝置,將12.3g(54mmol,1.0eq)2,4-二氯-6-苯基-[1,3,5]-三3a溶解在60ml乾燥THF中並用冰浴冷卻。將格任亞試劑轉移至滴液漏斗中,並緩慢加至3a的溶液中。在室溫下攪拌過夜後,將混合
物用100ml THF稀釋,並加入50ml的1M HCl。用水、乙醇和庚烷洗滌所形成的沈澱。藉由從甲苯熱萃取純化之後,獲得16g(39mmol,72%)的所要產物5a。
類似地獲得其他實施例:
步驟2b:將35g(150mmol,1.0eq)2,4-二氯-6-苯基-[1,3,5]三、35g(150mmol,1.0eq)二苯并噻吩-4-硼酸[108847-20-7]和18g(170mmol,1.10eq)碳酸鈉溶解在
300ml 1,4-二噁烷、300ml水和120ml甲苯中在惰性氛圍下。接著,添加1.8g(1.5mmol,0.01eq)肆(三苯膦)鈀並將混合物在110℃下回流過夜。反應完成後,添加100ml水並過濾沈澱的(48g)固體。將有機層分離,用水洗滌和經過硫酸鈉乾燥。溶劑蒸發之後,獲得另一13g的粗製產物。將合併的固體從甲苯再結晶二次以產生32g(86mmol,56%)的所要產物7a。
類似地獲得其他實施例:
步驟3b:在惰性氛圍下將30g(80mmol,1.0eq)的7a、21g(88mmol,1.1eq)9,9-二甲基-9H-茀-4-基-硼酸[1246022-50-3]和17g(160mmol,2.0eq)碳酸鈉溶解在400ml甲苯、250ml水和170ml乙醇中。接著,添加0.93g(0.80mmol,0.01eq)肆(三苯膦)鈀並將混合物在110℃下回流過夜。反應完成後,加300ml水並將沈澱的(36g)固體過濾。將有機層分離,用水洗滌和經過硫酸鈉乾燥。溶劑蒸發之後,獲得另一5.1g的粗製產物。藉由從甲苯/庚烷熱萃取,從甲苯/庚烷再結晶二次及昇華將合併的固體純化以產生20g(38mmol,47%)的所要產物9a。
類似地獲得其他實施例:
本發明此外關於一種製備式(I)化合物之方法,其包含下列之反應步驟:合成尚未含有三基或嘧啶基的化合物(I)之骨架;及在C-C偶合諸如Suzuki、Negishi、Yamamoto、Grignard-交叉或Stille偶合等等中、或C-N偶合諸如Buchwald或Ullmann偶合中反應該骨架。
下列實施例V1-V7和E1-E22(參見表1和2)顯示各種OLED之數據。
實施例V1-V7和E1-E22之基板預處理:將具有結構化ITO(50nm,氧化銦錫)之玻璃板塗佈20nm PEDOT:
PSS(聚(3,4-伸乙二氧基噻吩)聚(苯乙烯磺酸酯),來自Heraeus Precious Metals GmbH Germany之CLEVIOSTM PVP AI 4083,從水基溶液旋轉施加)及形成其上處理OLED之基板。
OLED原則上具有下列的層結構:基板/電洞傳輸層(HTL)/隨意中間層(IL)/電子阻擋層(EBL)/發光層(EML)/隨意電洞阻擋層(HBL)/電子傳輸層(ETL)/隨意電子注入層(EIL)及最後陰極。陰極係由厚度為100nm之鋁層形成。精確層結構表示於表1中。OLED製造中所使用之材料提呈於表3中。
所有材料係在真空室內藉由熱蒸氣沈積施加。發光層在此總是由至少一種基質材料(主體材料)和發光摻雜劑(發光體)組成,該發光摻雜劑藉由共蒸發而與基質材料或基質材料等以某體積比例摻混。詞句諸如IC1:M1:TEG1(55%:35%:10%)在此意指材料IC1係以55%之體積比例存在於層中,M1係以35%之比例存在於層中及TEG1係以10%之比例存在於層中。類似地,電子傳輸層亦可由二種材料之混合物所組成。
OLED係以標準方法示性。為此目的,從假設Lambertian發光剖面之電流/電壓/發光密度特徵線(IUL特徵線)測定電致發光光譜、電流效率(CE1000,於1000cd/m2測量,cd/A)、發光效率(LE1000,於1000cd/m2測量,lm/W)、外部量子效率(EQE1000,於1000cd/m2測量,%)和電壓(U1000,於1000cd/m2測量,V)。電致發
光(EL)光譜係記錄於1000cd/m2之發光密度並從EL光譜計算CIE 1931 x與y色座標。
對於所選實驗,測定壽命。壽命係定義為當OLED以恆定電流驅動時,發光密度從某初始光密度L1已降至某比例之後的時間。表2中之開始條件L0;j0=4000cd/m2和L1=70%指示LT欄中所表示之壽命對應於OLED自4000cd/m2之開始發光密度衰退至2800cd/m2所需要的時間,小時(h)。因此,開始條件L0;j0=20mA/cm2之壽命,L1=80%為在20mA/cm2之恆定電流下操作的OLED衰退至初始發光密度之80%所需要的時間。
各種OLED之裝置數據係總結於表2中。實施例V1-V7為根據技術現況之比較例。實施例E1-E22顯示本發明OLED的數據。
在下段中,更詳細地描述幾個實施例以顯示本發明OLED的優點。
相較於技術現況的材料,本發明之化合物作為電子傳輸層和作為主體材料的使用導致顯著改良的OLED裝置數據,特別是關於裝置壽命。
與使用材料CE1和CE2之裝置相較,本發明材料(1)和(187)與LiQ混合而使用於ETL中導致改良之LT(實施例V1和V2分別與E1和E3之比較)。另外,相較於材料
CE3(其為3-(9,9-二甲基茀基)三材料),本發明化合物(186)(其與CE3相同,除了其為4-(9,9-二甲基茀基)三)當以作為三重態綠色OLED中的主體測試時,導致LT效率之顯著改善(參見V3對E2)。亦應注意:相較於CE1(樣品V1,其像CE6,但其中苯基替代三上之4-(9,9-二甲基茀)基團)比較,CE6(樣品V6)(其為三上具有9,9’-螺聯茀取代基之4-(9,9-二甲基茀)三)很難產生任何改良。
Claims (15)
- 一種式(IV)和(V)之化合物,其中:Z1和Z2在每次出現時相同或不同地為H,D,F,Cl,Br,I,CHO,N(Ar1)2,C(=O)Ar1,P(=O)(Ar1)2,S(=O)Ar1,S(=O)2Ar1,CR2=CR2Ar1,CN,NO2,Si(R1)3,B(OR1)2,B(R1)2,B(N(R1)2)2,OSO2R1,具有1至40個C原子之直鏈烷基、烷氧基或烷硫基(thioalkoxy)或具有2至40個C原子之直鏈烯基或炔基或具有3至40個C原子之支鏈或環狀烷基、烯基、炔基、烷氧基或烷硫基(彼等各自可經一或多個基團R1取代,其中一或多個CH2基團可經(R1)C=C(R1)、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=N(R1)、P(=O)(R1)、SO、SO2、N(R1)2、O、S或CON(R1)2置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換),或具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R1取代),或具有5至60個芳族環原子之芳氧基或雜芳氧基(其可經一或多個基團R1取代),及其中Z1和Z2不形成雙-螺聯茀;Y1和Y2在每次出現時相同或不同地為D,F,Cl,Br,I,CHO,N(Ar1)2,C(=O)Ar1,P(=O)(Ar1)2,S(=O)Ar1,S(=O)2Ar1,(R1)C=C(R1)Ar1,CN,NO2,Si(R1)3,B(OR1)2,B(R1)2,B(N(R1)2)2,OSO2R1,具有1至40個C原子之直鏈烷基、烷氧基或烷硫基或具有2至40個C原子之直鏈烯基或炔基或具有3至40個C原子之支鏈或環狀烷基、烯基、炔基、烷氧基或烷硫基(彼等各自可經一或多個基團R1取代,其中一或多個CH2基團可經(R1)C=C(R1)、C≡C、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=N(R1)2、P(=O(R1)2、SO、SO2、N(R1)2、O、S或CON(R1)2置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換),或具有5至60個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R1取代),或具有5至60個芳族環原子之芳氧基或雜芳氧基(其可經一或多個基團R1取代),或此等系統的組合;二或多個相鄰的取代基Y1或Y2彼此也可形成稠合的單-或多環脂族或芳族或雜芳族環系統;Ar1和Ar2在每次出現時相同或不同地為具有5至23個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個基團R1取代),其先決條件為雜芳族環系統係經由碳-碳鍵連接;R1在每次出現時相同或不同地選自由下列所組成之群組:H,D,F,Cl,Br,I,CN,Si(R2)3,具有1至40個C原子之直鏈烷基、烷氧基或烷硫基或具有3-40個C原子之 支鏈或環狀烷基、烷氧基或烷硫基(其可經一或多個基團R2取代,其中一或多個非相鄰的CH2基團各自可經C(R2)=C(R2)、Si(R2)2、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2置換及其中一或多個H原子可經D、F、Cl、Br或I置換),具有6至40個碳原子的芳族或雜芳族環系統(其可經一或多個基團R2取代),具有5至60個芳族環原子之芳氧基(其可經一或多個基團R2取代),或具有5至60個芳族環原子之芳烷基(其可經一或多個基團R2取代),其中隨意地二或多個相鄰的取代基R1可彼此形成單-或多環脂族、芳族或雜芳族環系統(其可經一或多個基團R2取代);其中R2係選自由下列所組成之群組:H、D、F、具有1至20個碳原子之脂族烴基或具有5至30個C原子之芳族或雜芳族環系統,其中二或多個相鄰的取代基R2可彼此形成單-或多環脂族、芳族或雜芳族環系統;X在每次出現時相同或不同地為CR1或N,其先決條件為至少一個X表示N;L在每次出現時相同或不同地為具有5-30個芳族環原子之芳族或雜芳族環系統,其可經一或多個非芳族基團R1取代;c和d各自相同或不同地為0或1,其先決條件為c或d中之至少一者為1;e和f各自相同或不同地為0、1、2或3;及n在每次出現時相同或不同地為0或1。
- 如請求項1之化合物,其中Z1和Z2為相同 的取代基且彼此不在茀核的9位以外的任何位置連接。
- 如請求項1至3中任一項之化合物,其中e和f皆為0。
- 如請求項1至3中任一項之化合物,其中n為0。
- 如請求項1或2之化合物,其中每當c或d不為0時,兩個X基團皆為氮。
- 如請求項3之化合物,其中兩個X基團皆為氮。
- 如請求項1或2之化合物,其中每當c或d不為0時,一個X為氮,且另一個X為CR1。
- 如請求項3之化合物,其中一個X為氮,且另一個X為CR1。
- 如請求項1之化合物,其中Ar1和Ar2係選自由下列所組成之群組:苯,鄰-、間-或對-聯苯,鄰- 、間-、對-或支鏈聯三苯,萘基,聯伸三苯,9,9-二烷基茀基,N-苯基咔唑,二苯并呋喃和二苯并噻吩。
- 一種寡聚物、聚合物或樹枝狀聚合物,其含有一或多種如請求項1至10中一或多項之化合物,其中存在從該化合物連接至該聚合物、寡聚物或樹枝狀聚合物之一或多個鍵而非取代基存在於一或多個位置上。
- 一種調配物,其包含至少一種如請求項1至10中一或多項之化合物或如請求項12之寡聚物、聚合物或樹枝狀聚合物及至少一種溶劑。
- 一種電子裝置,其包含至少一種如請求項1至10中一或多項之化合物或如請求項12之寡聚物、聚合物或樹枝狀聚合物,其係選自由下列所組成之群組:有機電致發光裝置、有機積體電路、有機場效電晶體、有機薄膜電晶體、有機發光電晶體、有機太陽能電池、染料敏化之有機太陽能電池、有機光學偵測器、有機感光器(photoreceptor)、有機場淬滅裝置、有機發光電化學電池、有機雷射二極體及有機電漿子發射裝置。
- 一種有機電致發光裝置,其特徵在於如 請求項1至10中一或多項之化合物或如請求項12之寡聚物、聚合物或樹枝狀聚合物係用作下列一或多者:磷光或螢光發光體之基質材料、電子阻擋或激子阻擋層、電荷產生層、電洞阻擋層、或電子傳輸層。
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-
2016
- 2016-07-01 CN CN201680044327.6A patent/CN107922359A/zh active Pending
- 2016-07-01 EP EP16734191.6A patent/EP3328841B1/en active Active
- 2016-07-01 US US15/748,437 patent/US11098019B2/en active Active
- 2016-07-01 JP JP2018504890A patent/JP6839697B2/ja active Active
- 2016-07-01 EP EP23202035.4A patent/EP4301110A3/en active Pending
- 2016-07-01 KR KR1020187005481A patent/KR20180031766A/ko not_active Application Discontinuation
- 2016-07-01 WO PCT/EP2016/001117 patent/WO2017016630A1/en active Application Filing
- 2016-07-27 TW TW111109932A patent/TW202225147A/zh unknown
- 2016-07-27 TW TW109134170A patent/TWI761977B/zh active
- 2016-07-27 TW TW105123770A patent/TWI707845B/zh active
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JP2018531883A (ja) | 2018-11-01 |
TWI707845B (zh) | 2020-10-21 |
EP4301110A2 (en) | 2024-01-03 |
TW202225147A (zh) | 2022-07-01 |
TWI761977B (zh) | 2022-04-21 |
EP3328841B1 (en) | 2023-10-11 |
KR20180031766A (ko) | 2018-03-28 |
WO2017016630A1 (en) | 2017-02-02 |
EP3328841A1 (en) | 2018-06-06 |
JP2022166114A (ja) | 2022-11-01 |
US11098019B2 (en) | 2021-08-24 |
EP4301110A3 (en) | 2024-04-10 |
JP7121817B2 (ja) | 2022-08-18 |
JP6839697B2 (ja) | 2021-03-10 |
JP2021098707A (ja) | 2021-07-01 |
CN107922359A (zh) | 2018-04-17 |
TW201718526A (zh) | 2017-06-01 |
US20180222872A1 (en) | 2018-08-09 |
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