TWI530496B - 用於有機發光裝置之雙咔唑化合物 - Google Patents
用於有機發光裝置之雙咔唑化合物 Download PDFInfo
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- TWI530496B TWI530496B TW100129851A TW100129851A TWI530496B TW I530496 B TWI530496 B TW I530496B TW 100129851 A TW100129851 A TW 100129851A TW 100129851 A TW100129851 A TW 100129851A TW I530496 B TWI530496 B TW I530496B
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- compound
- heteroaryl
- aryl
- organic
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- 150000001875 compounds Chemical class 0.000 title claims description 56
- 239000010410 layer Substances 0.000 claims description 79
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 26
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 26
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 26
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000012044 organic layer Substances 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 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 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000004305 biphenyl Substances 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 239000002019 doping agent Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000010129 solution processing Methods 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 125000005580 triphenylene group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 description 64
- 239000003446 ligand Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- -1 electrodes Substances 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000004888 barrier function Effects 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 150000004696 coordination complex Chemical class 0.000 description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000005693 optoelectronics Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 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 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- OYIGWMXXIFYAGD-UHFFFAOYSA-N 3-iodo-9h-carbazole Chemical compound C1=CC=C2C3=CC(I)=CC=C3NC2=C1 OYIGWMXXIFYAGD-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- QNOYAVVYUIDSPZ-UHFFFAOYSA-N C1=CC=CC2=CC3=CC=CC=C3C=C12.O1C=NC=C1 Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C12.O1C=NC=C1 QNOYAVVYUIDSPZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 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
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- OSCVWUWFFQLESU-UHFFFAOYSA-N hydrazine pyrazine Chemical compound N1=CC=NC=C1.NN OSCVWUWFFQLESU-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- RYDICHIKLKVOEJ-UHFFFAOYSA-N oxadiazepine Chemical compound O1C=CC=CN=N1 RYDICHIKLKVOEJ-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- YEZKRPIRIDAQQS-UHFFFAOYSA-N selenopheno[3,2-b]pyridine Chemical compound C1=CC=C2[se]C=CC2=N1 YEZKRPIRIDAQQS-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
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- 150000003852 triazoles Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- WZOYYTKAWYSOAN-UHFFFAOYSA-N C(C(C=CC=C1)C1=C1)C=C1[n]1c(ccc(-c(cc2)cc(c3c4cccc3)c2[n]4-c2nc(-c3cc(cccc4)c4c4ccccc34)nc(-c3cc4ccccc4c4c3cccc4)n2)c2)c2c2c1cccc2 Chemical compound C(C(C=CC=C1)C1=C1)C=C1[n]1c(ccc(-c(cc2)cc(c3c4cccc3)c2[n]4-c2nc(-c3cc(cccc4)c4c4ccccc34)nc(-c3cc4ccccc4c4c3cccc4)n2)c2)c2c2c1cccc2 WZOYYTKAWYSOAN-UHFFFAOYSA-N 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—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 three or more hetero rings
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- C07D401/14—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 three or more hetero 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
- C07D405/14—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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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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Description
本發明係關於有機發光裝置(OLED)。更特定言之,本發明係關於包含雙咔唑之磷光有機材料,該雙咔唑在9位處具有含氮雜環。
本申請案主張2010年8月20日申請之國際申請案第PCT/US2010/046,218號之優先權,該案揭示內容以全文引用的方式明確併入本文中。
所主張之本發明係代表及/或聯合以下各方中之一或多者依據大學企業共同研究協定(joint university corporation research agreement)而提出:密歇根州大學(University of Michigan)董事會、普林斯頓大學(Princeton University)董事會、南加州大學(The University of Southern California)董事會及通用顯示器公司(Universal Display Corporation)。該協定在提出所主張之發明之日及之前即已生效且所主張之發明係由在該協定範疇內所進行之活動而提出。
利用有機材料之光電裝置由於許多原因而變得日益合乎需要。用於製造該等裝置之許多材料相對便宜,因此有機光電裝置有可能具有優於無機裝置之成本優勢。此外,有機材料之固有性質(諸如其可撓性)可使其良好適用於特定應用,諸如在可撓性基板上製造。有機光電裝置之實例包括有機發光裝置(OLED)、有機光電晶體、有機光伏打電池及有機光偵測器。對於OLED,有機材料可具有優於習知材料之效能優勢。舉例而言,有機發射層發射之光之波長通常可容易地用適當摻雜劑來調諧。
當跨OLED施加電壓時,該等裝置將利用發光之有機薄膜。OLED正日益成為用於諸如平板顯示器、照明及背光之應用的值得關注之技術。若干OLED材料及組態描述於美國專利第5,844,363號、第6,303,238號及第5,707,745號中,其均以全文引用的方式併入本文中。
磷光發射分子之一個應用為全色顯示器。關於該種顯示器之工業標準需要適合於發射特定色彩(稱為「飽和」色)之像素。詳言之,該等標準需要飽和紅色、綠色及藍色像素。色彩可使用此項技術中熟知的CIE座標量測。
綠光發射分子之一實例為參(2-苯基吡啶)銥,表示為Ir(ppy)3,其具有結構:
在此圖及下文之圖式中,以直線描繪氮至金屬(此處為Ir)之配位鍵(dative bond)。
如本文中所用之術語「有機」包括可用於製造有機光電裝置之聚合材料及小分子有機材料。「小分子」係指不為聚合物之任何有機材料,且「小分子」實際上可能相當大。在一些情況下,小分子可包括重複單元。舉例而言,使用長鏈烷基作為取代基並不會將某一分子自「小分子」類別中移除。小分子亦可例如作為聚合物主鏈上之側基或作為主鏈之一部分併入聚合物中。小分子亦可充當樹狀體之核心部分,該樹狀體由建立於該核心部分上之一系列化學殼層組成。樹狀體之核心部分可為螢光或磷光小分子發射體。樹狀體可為「小分子」,且咸信目前用於OLED領域之所有樹狀體均為小分子。
如本文中所用,「頂部」意謂離基板最遠,而「底部」意謂距基板最近。在將第一層描述為「安置於」第二層「上方」時,第一層係安置於離基板較遠處。除非指定第一層與第二層「接觸」,否則第一層與第二層之間可存在其他層。舉例而言,即使陰極與陽極之間存在各種有機層,陰極亦可被描述為「安置於」陽極「上方」。
如本文中所用,「溶液可加工」意謂能夠溶解、分散或傳輸於液體介質中及/或自液體介質沈積,該液體介質呈溶液或懸浮液形式。
當咸信配位體直接促成發射材料之光敏性質時,配位體可稱為「光敏性」配位體。當咸信配位體並不促成發射材料之光敏性質時,配位體可稱為「輔助性」配位體,但輔助性配位體可能改變光敏性配位體之性質。
如本文中所用且如熟習此項技術者通常所理解,若第一能階較接近於真空能階,則第一「最高佔用分子軌域」(Highest Occupied Molecular Orbital,HOMO)或「最低未佔用分子軌域」(Lowest Unoccupied Molecular Orbital,LUMO)之能階「大於」或「高於」第二HOMO或LUMO能階。由於經量測,游離電位(IP)相對於真空能階為負能量,故較高HOMO能階對應於具有較小絕對值之IP(IP為較大負值(less negative))。類似地,較高LUMO能階對應於具有較小絕對值之電子親和力(EA)(EA為較大負值)。在頂部為真空能階之習知能階圖上,一種材料之LUMO能階高於同一材料之HOMO能階。「較高」HOMO或LUMO能階看起來比「較低」HOMO或LUMO能階更接近於該圖的頂部。
如本文中所用且如熟習此項技術者通常所瞭解,若第一功函數具有較高絕對值,則第一功函數「大於」或「高於」第二功函數。由於經量測,功函數通常相對於真空能階為負數,故此意謂「較高」功函數為較大之負值(more negative)。在頂部為真空能階之習知能階圖上,「較高」功函數圖示為在向下方向上離真空能階較遠。因此,HOMO及LUMO能階之定義遵循與功函數不同的慣例。
關於OLED之更多詳情及上述定義可見於美國專利第7,279,704號中,其以全文引用的方式併入本文中。
提供包含雙咔唑之化合物。該等化合物具有下式:
R1、R2、R3及R4可表示單取代、雙取代、三取代或四取代。R1、R2、R3及R4獨立地選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群。Ar1、Ar2及Ar3獨立地選自芳基或雜芳基。Ar1、Ar2及Ar3可經進一步取代。X為C或N。
在一態樣中,Ar1、Ar2及Ar3獨立地選自由苯基、吡啶、萘、聯苯、聯三苯、茀、二苯并呋喃、二苯并噻吩、菲及聯伸三苯組成之群。Ar1、Ar2及Ar3獨立地經選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群的取代基進一步取代,但取代基不為與Ar1、Ar2及Ar3直接稠合之芳基或雜芳基。Ar1及Ar2較佳獨立地選自由苯基、吡啶及萘組成之群。Ar3較佳係選自由苯基、聯苯、二苯并呋喃及二苯并噻吩組成之群。
在另一態樣中,R1、R2、R3及R4為氫。
亦提供包含雙咔唑之化合物之特定實例。詳言之,化合物係選自由以下組成之群:
亦提供包含有機發光裝置之第一裝置。該裝置進一步包含陽極、陰極及安置於陽極與陰極之間的有機層。有機層包含如上文所描述之式I化合物。
R1、R2、R3及R4可表示單取代、雙取代、三取代或四取代。R1、R2、R3及R4獨立地選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群。Ar1、Ar2及Ar3獨立地選自芳基或雜芳基。Ar1、Ar2及Ar3可經進一步取代。X為C或N。
在一態樣中,Ar1、Ar2及Ar3獨立地選自由苯基、吡啶、萘、聯苯、聯三苯、茀、二苯并呋喃、二苯并噻吩、菲及聯伸三苯組成之群。Ar1、Ar2及Ar3獨立地經選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群的取代基進一步取代,但取代基不為與Ar1、Ar2及Ar3直接稠合之芳基或雜芳基。Ar1及Ar2較佳獨立地選自由苯基、吡啶及萘組成之群。Ar3較佳係選自由苯基、聯苯、二苯并呋喃及二苯并噻吩組成之群。
在另一態樣中,R1、R2、R3及R4為氫。
亦提供含有包含雙咔唑之化合物之裝置的特定實例。詳言之,化合物係選自由化合物1至化合物184組成之群。
在一態樣中,使用溶液加工來沈積有機層。
在一態樣中,有機層為發射層且式I化合物為主體。
在另一態樣中,有機層進一步包含具有下式之發射性摻雜劑:
在一態樣中,第一裝置為消費型產品。在另一態樣中,第一裝置為有機發光裝置。
通常,OLED包含至少一個有機層,其安置於陽極與陰極之間且與陽極及陰極電連接。當施加電流時,陽極注入電洞且陰極注入電子至有機層中。所注入之電洞及電子各自朝帶相反電荷之電極遷移。當電子及電洞定位於同一分子上時,形成「激子」,其為具有激發能態之定域電子-電洞對。當激子經由光發射機制弛豫時,發射光。在一些情況下,激子可定位於準分子或激發複合物(exciplex)上。亦可能出現諸如熱弛豫之非輻射機制,但通常認為其不合需要。
最初的OLED係使用自單重態發光(「螢光」)之發射分子,如例如美國專利第4,769,292號中所揭示,其以全文引用的方式併入本文中。螢光發射通常在小於10奈秒(nanosecond)之時段內發生。
最近已說明具有自三重態發光(「磷光」)之發射材料的OLED。Baldo等人,「Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices」,Nature,第395卷,151-154,1998;(「Baldo-I」)及Baldo等人,「Very high-efficiency green organic light-emitting devices based on electrophosphorescence」,Appl. Phys. Lett.,第75卷,第3期,4-6(1999)(「Baldo-II」),兩篇文獻均以全文引用的方式併入本文中。磷光更詳細地描述於美國專利第7,279,704號,第5-6行,其以引用的方式併入本文中。
圖1展示有機發光裝置100。該等圖式未必按比例描繪。裝置100可包括基板110、陽極115、電洞注入層120、電洞傳輸層125、電子阻擋層130、發射層135、電洞阻擋層140、電子傳輸層145、電子注入層150、保護層155及陰極160。陰極160為具有第一導電層162及第二導電層164之複合陰極。裝置100可藉由依次沈積所描述之層來製造。該等不同層之性質及功能以及實例材料更詳細地描述於US 7,279,704,第6-10行中,其以引用的方式併入本文中。
可提供各該等層之更多實例。舉例而言,可撓且透明之基板-陽極組合係揭示於美國專利第5,844,363號中,其以全文引用的方式併入本文中。p摻雜之電洞傳輸層之實例為按50:1之莫耳比摻雜F4-TCNQ之m-MTDATA,如美國專利申請公開案第2003/0230980號中所揭示,該案以全文引用的方式併入。發射材料及主體材料之實例揭示於Thompson等人之美國專利第6,303,238號中,其以全文引用的方式併入。n摻雜之電子傳輸層的實例為按1:1之莫耳比摻雜Li之BPhen,如美國專利申請公開案第2003/0230980號中所揭示,其以全文引用的方式併入。美國專利第5,703,436號及第5,707,745號(其以全文引用的方式併入)揭示陰極實例,包括具有金屬薄層之複合陰極,諸如上覆透明、導電、濺鍍沈積之ITO層的Mg:Ag。關於阻擋層之理論及使用更詳細地描述於美國專利第6,097,147號及美國專利申請公開案第2003/0230980號中,其均以全文引用的方式併入。注入層之實例提供於美國專利申請公開案第2004/0174116號中,其以全文引用的方式併入。關於保護層之說明可見於美國專利申請公開案第2004/0174116號中,其以全文引用的方式併入。
圖2顯示倒置式OLED 200。該裝置包括基板210、陰極215、發射層220、電洞傳輸層225及陽極230。裝置200可藉由依次沈積所描述之層來製造。由於最常見之OLED組態中陰極安置於陽極上方,而裝置200中陰極215安置於陽極230下方,故裝置200可稱為「倒置式」OLED。與有關裝置100所描述類似之材料可用於裝置200之相應層中。圖2提供一個如何自裝置100之結構省略一些層之實例。
圖1及圖2中說明之簡單層狀結構係以非限制性實例提供,且應理解本發明之實施例可與多種其他結構結合使用。所描述之特定材料及結構本質上為例示性的,且可使用其他材料及結構。可藉由以不同方式組合所描述之各種層來獲得功能性OLED,或可基於設計、效能及成本因素完全省去各層。亦可包括未具體描述之其他層。可使用除具體描述之材料以外的材料。儘管本文中所提供之許多實例將各種層描述為包含單一材料,但應瞭解可使用材料之組合,諸如主體與摻雜劑之混合物,或更一般的混合物。該等層亦可具有各種子層。本文中對各種層給出之名稱並不意欲成為嚴格限制。舉例而言,在裝置200中,電洞傳輸層225傳輸電洞且注入電洞至發射層220中,且可描述為電洞傳輸層或電洞注入層。在一實施例中,OLED可描述為具有安置於陰極與陽極之間的「有機層」。該有機層可包含單一層,或如(例如)關於圖1及2所描述一般,可進一步包含具有不同有機材料之多個層。
亦可使用未具體描述之結構及材料,諸如包含聚合材料之OLED(PLED),諸如Friend等人之美國專利第5,247,190號中所揭示者,其以全文引用的方式併入。作為另一實例,可使用具有單一有機層之OLED。可堆疊OLED,如例如Forrest等人之美國專利第5,707,745號中所述,其以全文引用的方式併入。OLED結構可與圖1及圖2中說明之簡單層狀結構不同。舉例而言,基板可包括傾斜反射表面以改良外部耦合,諸如Forrest等人之美國專利第6,091,195號中所述之台面結構(mesa structure),及/或如Bulovic等人之美國專利第5,834,893號中所述之凹槽結構(pit structure),該等專利均以全文引用之方式併入。
除非另有說明,否則可藉由任何合適的方法沈積各種實施例之任何層。對於有機層,較佳方法包括熱蒸發法;噴墨法(ink-jet),諸如美國專利第6,013,982號及第6,087,196號中所述,其均以全文引用的方式併入;有機氣相沈積法(organic vapor phase deposition,OVPD),諸如Forrest等人之美國專利第6,337,102號中所述,其以全文引用的方式併入;及藉由有機蒸汽噴印(organic vapor jet printing,OVJP)進行之沈積,諸如美國專利申請案第10/233,470號中所述,其以全文引用的方式併入。其他適當的沈積方法包括旋塗法及其他基於溶液之方法。基於溶液之方法較佳在氮氣或惰性氛圍中進行。對於其他層,較佳方法包括熱蒸發法。較佳圖案化方法包括透過光罩沈積、冷熔接(諸如美國專利第6,294,398號及第6,468,819號中所述,其均以全文引用的方式併入)及結合諸如噴墨及OVJD之一些沈積方法的圖案化方法。亦可使用其他方法。待沈積之材料可經改質以使其與特定沈積方法相容。舉例而言,可在小分子中使用分支或未分支且較佳含有至少3個碳之取代基(諸如烷基及芳基)以增強其經受溶液加工的能力。可使用具有20或20個碳以上之取代基且3至20個碳為較佳範圍。由於不對稱材料可具有較低之再結晶傾向,故具有不對稱結構之材料之溶液可加工性可優於具有對稱結構之材料。樹狀體取代基可用於增強小分子經受溶液加工之能力。
根據本發明之實施例製造之裝置可併入多種消費型產品中,包括平板顯示器、電腦監控器、電視、廣告牌、室內或室外照明燈及/或信號燈、抬頭顯示器、完全透明顯示器、可撓性顯示器、雷射印表機、電話、手機、個人數位助理(PDA)、膝上型電腦、數位攝影機、攝錄影機、取景鏡、微型顯示器、運載工具、大面積牆、劇場或運動場屏幕,或標誌(sign)。可使用各種控制機構來控制根據本發明製造之裝置,包括被動型矩陣及主動型矩陣。許多裝置欲用於人類感覺舒適之溫度範圍內,諸如18℃至30℃,且更佳為室溫(20-25℃)。
本文中所描述之材料及結構可應用於除OLED以外的裝置中。舉例而言,諸如有機太陽能電池及有機光偵測器之其他光電裝置可使用該等材料及結構。更一般而言,諸如有機電晶體之有機裝置可使用該等材料及結構。
術語鹵基、鹵素、烷基、環烷基、烯基、炔基、芳基烷基、雜環基、芳基、芳族基及雜芳基為此項技術中已知的且定義於US 7,279,704,第31-32行中,其以引用的方式併入。
提供新穎的含有雙咔唑之化合物(說明於圖3中)。更特定言之,該等化合物含有3,3'-雙咔唑核心及在9位處之三嗪或嘧啶取代。該等化合物可用作磷光OLED之主體。
先前已描述用作OLED材料之含有咔唑之化合物。詳言之,3,3'-雙咔唑化合物具有優良的電洞傳輸性質,但對電子具有弱穩定性。經烷基及芳基取代之3,3'-雙咔唑化合物已被用作OLED中之電洞傳輸材料及主體;然而,該等化合物亦具有不平衡之電荷傳輸性質及弱電子穩定性且可能使裝置具有較低效率及有限的使用壽命。舉例而言,經二芳基取代之3,3'-雙咔唑(亦即H1)具有約5.6 eV之HOMO,具有極佳之電洞傳輸性,但電子傳輸性及穩定性較差。因此,文獻中報導之3,3'-雙咔唑化合物之使用受到限制。
在本發明中,將含氮缺電子雜環引入3,3'-雙咔唑化合物中。詳言之,化合物含有3,3'-雙咔唑核心及在9位處之三嗪或嘧啶取代。含氮雜環調諧HOMO/LUMO能階且增加化合物對電子之穩定性。此外,該等化合物含有供體部分(亦即雙咔唑)及受體部分(亦即缺電子含氮雜環)。在不受理論約束的情況下,咸信該等供體-受體型分子可縮減單重態及三重態能隙,且改良對電洞及電子之穩定性。因此,該等含有氮雜環之3,3'-雙咔唑化合物可提供具有較佳穩定性及較低操作電壓之裝置。
提供包含雙咔唑之化合物。該等化合物具有下式:
R1、R2、R3及R4可表示單取代、雙取代、三取代或四取代。R1、R2、R3及R4獨立地選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群。Ar1、Ar2及Ar3獨立地選自芳基或雜芳基。Ar1,Ar2及Ar3可經進一步取代。X為C或N。
在一態樣中、Ar1、Ar2及Ar3獨立地選自由苯基、吡啶、萘、聯苯、聯三苯、茀、二苯并呋喃、二苯并噻吩、菲及聯伸三苯組成之群,且Ar1、Ar2及Ar3獨立地經選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群的取代基進一步取代,但取代基不為與Ar1、Ar2及Ar3直接稠合之芳基或雜芳基。Ar1及Ar2較佳獨立地選自由苯基、吡啶及萘組成之群。Ar3較佳係選自由苯基、聯苯、二苯并呋喃及二苯并噻吩組成之群。
在另一態樣中,R1、R2、R3及R4為氫。
亦提供包含雙咔唑之化合物之特定實例。詳言之,化合物係選自由以下組成之群:
亦提供包含有機發光裝置之第一裝置。該裝置進一步包含陽極、陰極及安置於陽極與陰極之間的有機層。有機層包含如上文所描述之式I化合物。
R1、R2、R3及R4可表示單取代、雙取代、三取代或四取代。R1、R2、R3及R4獨立地選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群。Ar1、Ar2及Ar3獨立地選自芳基或雜芳基。Ar1、Ar2及Ar3可經進一步取代。X為C或N。
在一態樣中,Ar1、Ar2及Ar3獨立地選自由苯基、吡啶、萘、聯苯、聯三苯、茀、二苯并呋喃、二苯并噻吩、菲及聯伸三苯組成之群。Ar1、Ar2及Ar3獨立地經選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群的取代基進一步取代,但取代基不為與Ar1、Ar2及Ar3直接稠合之芳基或雜芳基。Ar1及Ar2較佳獨立地選自由苯基、吡啶及萘組成之群。Ar3較佳係選自由苯基、聯苯、二苯并呋喃及二苯并噻吩組成之群。
在另一態樣中,R1、R2、R3及R4為氫。
亦提供含有包含雙咔唑之化合物之裝置的特定實例。詳言之,化合物係選自由化合物1至化合物184組成之群。
在一態樣中,使用溶液加工方法來沈積有機層。
在一態樣中,有機層為發射層且式I化合物為主體。
在另一態樣中,有機層進一步包含具有下式之發射性摻雜劑:
在一態樣中,第一裝置為消費型產品。在另一態樣中,第一裝置為有機發光裝置。
本文中描述之適用於有機發光裝置中之特定層的材料可與該裝置中存在之多種其他材料組合使用。舉例而言,本文中揭示之發射性摻雜劑可與多種主體、傳輸層、阻擋層、注入層、電極及其他可能存在之層結合使用。下文描述或提及之材料為可與本文中揭示之化合物組合使用之材料的非限制性實例,且熟習此項技術者可容易地查閱文獻以鑑別其他可組合使用之材料。
本發明中所用電洞注入/傳輸材料不受特定限制且可使用任何化合物,限制條件為該化合物通常用作電洞注入/傳輸材料。該材料之實例包括(但不限於):酞菁或卟啉衍生物;芳族胺衍生物;吲哚并咔唑衍生物;含有氟代烴之聚合物;具有傳導性摻雜劑之聚合物;傳導性聚合物,諸如PEDOT/PSS;衍生自諸如膦酸及矽烷衍生物之化合物之自組裝單體;金屬氧化物衍生物,諸如MoOx;p型半傳導性有機化合物,諸如1,4,5,8,9,12-六氮雜三伸苯基六甲腈;金屬錯合物及可交聯化合物。
用於HIL或HTL中之芳族胺衍生物之實例包括(但不限於)以下一般結構:
Ar1至Ar9中之每一者係選自由芳族烴環狀化合物組成之群,諸如苯、聯苯、聯三苯、聯伸三苯、萘、蒽、萉、菲、茀、芘、、苝、薁;由芳族雜環化合物組成之群,諸如二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚并咔唑、吡啶基吲哚、吡咯并二吡啶、吡唑、咪唑、三唑、噁唑、噻唑、噁二唑、噁三唑、二噁唑、噻二唑、吡啶、噠嗪、嘧啶、吡嗪、三嗪、噁嗪、噁噻嗪、氧二氮雜環己烯、吲哚、苯并咪唑、吲唑、吲哚嗪、苯并噁唑、苯并異噁唑、苯并噻唑、喹啉、異喹啉、啉、喹唑啉、喹喏啉、啶、酞嗪、喋啶、二苯并哌喃(xanthene)、吖啶、吩嗪、啡噻嗪、啡噁嗪、苯并呋喃并吡啶、呋喃并二吡啶、苯并噻吩并吡啶、噻吩并二吡啶、苯并硒酚并吡啶及硒酚并吡啶;及由2至10個環狀結構單元組成之群,其為選自芳族烴環狀基團及芳族雜環基團之相同類型或不同類型之基團且彼此直接鍵結或經氧原子、氮原子、硫原子、矽原子、磷原子、硼原子、鏈結構單元及脂族環狀基團中之至少一者鍵結。其中各Ar經選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基烷基、雜烷基、芳基及雜芳基組成之群的取代基進一步取代。
在一態樣中,Ar1至Ar9獨立地選自由以下組成之群:
k為1至20之整數;X1至X8為CH或N;Ar1具有以上定義之相同基團。
用於HIL或HTL中之金屬錯合物之實例包括(但不限於)以下通式:
M為原子量大於40之金屬;(Y1-Y2)為雙齒配位體,Y1及Y2獨立地選自C、N、O、P及S;L為輔助性配位體;m為1至可連接至金屬之配位體之最大數目的整數值;且m+n為可連接至金屬之配位體之最大數目。
在一態樣中,(Y1-Y2)為2-苯基吡啶衍生物。
在另一態樣中,(Y1-Y2)為碳烯配位體。
在另一態樣中,M係選自Ir、Pt、Os及Zn。
在另一態樣中,與Fc+/Fc對相比,金屬錯合物在溶液中具有小於約0.6 V之最小氧化電位。
本發明之有機EL裝置之發光層較佳至少含有金屬錯合物作為發光材料且可含有使用金屬錯合物作為摻雜材料之主體材料。主體材料之實例不受特定限制且可使用任何金屬錯合物或有機化合物,限制條件為主體之三重態能量大於摻雜劑之三重態能量。
用作主體之金屬錯合物之實例較佳具有以下通式:
M為金屬;(Y3-Y4)為雙齒配位體,Y3及Y4獨立地選自C、N、O、P及S;L為輔助性配位體;m為1至可連接至金屬之配位體之最大數目的整數值;且m+n為可連接至金屬之配位體之最大數目。
在一態樣中,金屬錯合物為:
(O-N)為雙齒配位體,其具有與原子O及N配價之金屬。
在另一態樣中,M係選自Ir及Pt。
在另一態樣中,(Y3-Y4)為碳烯配位體。
用作主體之有機化合物之實例係選自由芳族烴環狀化合物組成之群,諸如苯、聯苯、聯三苯、聯伸三苯、萘、蒽、萉、菲、茀、芘、、苝、薁;由芳族雜環化合物組成之群,諸如二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚并咔唑、吡啶基吲哚、吡咯并二吡啶、吡唑、咪唑、三唑、噁唑、噻唑、噁二唑、噁三唑、二噁唑、噻二唑、吡啶、噠嗪、嘧啶、吡嗪、三嗪、噁嗪、噁噻嗪、氧二氮雜環己烯、吲哚、苯并咪唑、吲唑、吲哚嗪、苯并噁唑、苯并異噁唑、苯并噻唑、喹啉、異喹啉、啉、喹唑啉、喹喏啉、啶、酞嗪、喋啶、二苯并哌喃、吖啶、吩嗪、啡噻嗪、啡噁嗪、苯并呋喃并吡啶、呋喃并二吡啶、苯并噻吩并吡啶、噻吩并二吡啶、苯并硒酚并吡啶及硒酚并吡啶;及由2至10個環狀結構單元組成之群,其為選自芳族烴環狀基團及芳族雜環基團之相同類型或不同類型之基團且彼此直接鍵結或經氧原子、氮原子、硫原子、矽原子、磷原子、硼原子、鏈結構單元及脂族環狀基團中之至少一者鍵結。其中各基團經選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基烷基、雜烷基、芳基及雜芳基組成之群的取代基進一步取代。
在一態樣中,主體化合物在分子中含有以下基團中之至少一者:
R1至R7獨立地選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基烷基、雜烷基、芳基及雜芳基組成之群,當其為芳基或雜芳基時,其具有與上述Ar類似之定義。
k為0至20之整數。
X1至X8係選自CH或N。
可使用電洞阻擋層(HBL)降低離開發射層之電洞及/或激子之數目。與缺乏阻擋層之類似裝置相比,裝置中存在該阻擋層可產生實質上較高效率。又,可使用阻擋層將發射限於OLED之所需區域。
在一態樣中,用於HBL中之化合物含有與上述用作主體相同之分子。
在另一態樣中,用於HBL中之化合物在分子中含有以下基團中之至少一者:
k為0至20之整數;L為輔助性配位體,m為1至3之整數。
電子傳輸層(ETL)可包括能夠傳輸電子之材料。電子傳輸層可為純質(未經摻雜)或經摻雜的。可使用摻雜來增強傳導性。ETL材料之實例不受特定限制且可使用任何金屬錯合物或有機化合物,限制條件為其通常被用於傳輸電子。
在一態樣中,用於ETL中之化合物在分子中含有以下基團中之至少一者:
R1選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基烷基、雜烷基、芳基及雜芳基組成之群,當其為芳基或雜芳基時,其具有與上述Ar類似之定義。
Ar1至Ar3具有與上述Ar類似之定義。
k為0至20之整數。
X1至X8選自CH或N。
在另一態樣中,用於ETL中之金屬錯合物含有(但不限於)以下通式:
(O-N)或(N-N)為雙齒配位體,其具有與原子O、N或N,N配價之金屬;L為輔助性配位體;m為1至可連接至金屬之配位體之最大數目的整數值。
在用於OLED裝置各層中之任何上述化合物中,連接至共軛環之氫原子可經部分或完全氘化。
本文中描述之適用於有機發光裝置中特定層的材料可與裝置中存在之多種其他材料組合使用。舉例而言,本文中揭示之發射性摻雜劑可與多種主體、傳輸層、阻擋層、注入層、電極及其他可能存在之層結合使用。下文描述或提及之材料為可與本文中揭示之化合物組合使用之材料的非限制性實例,且熟習此項技術者可容易地查閱文獻以鑑別其他可組合使用之材料。
除本文中揭示之材料外及/或與本文中揭示之材料組合,OLED中可使用許多電洞注入材料、電洞傳輸材料、主體材料、摻雜材料、激子/電洞阻擋層材料、電子傳輸及電子注入材料。可與本文中揭示之材料組合用於OLED中之材料的非限制性實例列於下表1中。表1列舉非限制性材料類別、各類別化合物之非限制性實例及揭示該等材料之參考文獻。
實驗
化合物實例
實例1. 合成化合物1
合成3-碘-9H-咔唑。加熱9H-咔唑(5.57 g,33.3 mmol)及KI(3.68 g,22.2 mmol)於AcOH(92 mL)中之溶液至100℃,保持1小時。KIO3(3.57 g,16.7 mmol)分數份添加至溶液中且在100℃下再攪拌所得混合物2小時。混合物傾入水(500 mL)中且藉由過濾收集沈澱並用熱水洗滌。於DCM中進行再結晶得到6.8 g(70%)呈白色固體狀之產物。
合成9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧硼 -2-基)-9H-咔唑。在-78℃下向3-溴-9-苯基-9H-咔唑(20.3 g,63 mmol)於THF(150 mL)中之溶液中添加47.25 mL(75.8 mmol)正丁基鋰(1.6 M之己烷溶液)。在-78℃下攪拌混合物1小時。21 mL(100 mmol)2-異丙氧基-4,4,5,5-四甲基-[1,3,2]-二氧硼添加至溶液中且所得混合物溫至室溫,並攪拌8小時。混合物傾入水中且用二氯甲烷萃取。有機萃取物用鹽水洗滌且經硫酸鎂乾燥。藉由旋轉蒸發移除溶劑且於己烷中進行再結晶,得到19.3 g(83%)呈白色固體狀之產物。
合成3-(9-苯基-9H-咔唑-3-基)-9H-咔唑。製備3-碘-9H-咔唑(879 mg,3.0 mmol)、Pd(PPh3)4(165 mg,0.15 mmol)、9-苯基-3-(4,4,5,5-四甲基-1,3,2-二氧硼-2-基)-9H-咔唑(1.29 g,4.5 mmol)及K3PO4(1.8 g,18.0 mmol)於二噁烷(5 mL)中之溶液。在氬氣氛圍下,在劇烈攪拌下加熱溶液至85℃保持48小時。混合物傾入水中且用DCM萃取。有機萃取物用鹽水洗滌且經MgSO4乾燥。藉由旋轉蒸發移除溶劑且於DCM中進行再結晶,得到900 mg(74%)產物。
合成9-(4,6-二苯基-1,3,5-三嗪-2-基)-3-(9-苯基-9H-咔唑-3-基)-9H-咔唑(化合物1)。在室溫下,在氬氣氛圍下攪拌氫化鈉(100 mg,3.0 mmol)及3-(9-苯基-9H-咔唑-3-基)-9H-咔唑(816 mg,2.0 mmol)於無水DMF(40 mL)中之溶液1小時。在室溫下,2-氯-4,6-二苯基-1,3,5-三嗪(448 mg,1.67 mmol)添加至溶液中,接著回流隔夜。混合物傾入水中且藉由過濾收集沈澱並用水、甲醇及DCM洗滌,得到800 mg(75%)黃色固體。
藉由高真空(<10-7托)熱蒸發來製造所有裝置實例。陽極為800 之氧化銦錫(ITO)。陰極由10 之LiF接著1000之Al組成。所有裝置在製造後立即以玻璃蓋封閉,由環氧樹脂密封於氮氣手套箱中(<1 ppm H2O及O2),且封裝內部併有吸濕劑。
如本文中使用,以下化合物具有以下結構:
提供特定裝置。裝置實例1及裝置實例2之有機堆疊自ITO表面依序由作為電洞注入層(HIL)之100 E1、作為電洞傳輸層(HTL)之300 4,4'-雙[N-(1-萘基)-N-苯基胺基]聯苯(α-NPD)、作為發射層(EML)之300 經E1摻雜之主體、作為阻擋層(BL)之100 H2及作為電子傳輸層(ETL)之400 Alq組成。
以與裝置實例1及裝置實例2類似之方式製造比較性裝置實例1及比較性裝置實例2,但使用H3作為主體。
裝置實例1及裝置實例2之裝置結構提供於表2中且相應之經量測裝置資料提供於表3中。
裝置實例1及裝置實例2展示具有化合物1作為主體及不同E1摻雜濃度之綠光PHOLED。比較實例使用H3(亦即CBP,常用PHOLED主體)作為主體。如可自表中看出,以化合物1作為主體之裝置與以H3作為主體之裝置相比,操作電壓相當,效率稍低。然而,裝置之操作壽命遠高於比較實例。裝置實例1之使用壽命幾乎為比較實例1之使用壽命的2倍(86小時對46小時)且裝置實例2之使用壽命幾乎為比較實例2之使用壽命的3倍(83小時對29小時)。因此,化合物1為用於磷光OLED之優良主體材料。
應理解,本文中所描述之各種實施例僅作為實例且不意欲限制本發明之範疇。舉例而言,在不偏離本發明之精神的情況下,本文中所描述之許多材料及結構可由其他材料及結構替代。因此,如熟習此項技術者將顯而易見,所主張之本發明可包括本文中所描述之特定實例及較佳實施例之變化。應理解,有關本發明為什麼起作用之各種理論不意欲為限制性的。
100...有機發光裝置
110...基板
115...陽極
120...電洞注入層
125...電洞傳輸層
130...電子阻擋層
135...發射層
140...電洞阻擋層
145...電子傳輸層
150...電子注入層
155...保護層
160...陰極
162...第一導電層
164...第二導電層
200...倒置式有機發光裝置
210...基板
215...陰極
220...發射層
225...電洞傳輸層
230...陽極
圖1展示有機發光裝置。
圖2展示不具有獨立電子傳輸層之倒置式有機發光裝置。
圖3展示在9位處具有含氮雜環取代之雙咔唑化合物。
(無元件符號說明)
Claims (12)
- 一種化合物,其具有下式:
- 如請求項1之化合物,其中Ar3係選自由苯基、吡啶、萘、聯苯、聯三苯、茀、二苯并呋喃、二苯并噻吩、菲及聯伸三苯(triphenylene)組成之群;且其中Ar1、Ar2及Ar3獨立地經選自由氫、烷基、烷氧基、胺基、烯基、炔基、芳基及雜芳基組成之群的取代基進一步取代,其中該取代基不為與Ar1、Ar2及Ar3直接稠合之芳基或雜芳基,且其中該烷基、烷氧基、烯基、炔基、芳基及雜芳基係如請求項1所定義。
- 如請求項1之化合物,其中Ar1及Ar2獨立地選自由吡啶及萘組成之群。
- 如請求項1之化合物,其中Ar3係選自由苯基、聯苯、二苯并呋喃及二苯并噻吩組成之群。
- 如請求項1之化合物,其中R1、R2、R3及R4為氫。
- 一種化合物,其係選自由以下組成之群:
- 一種包含有機發光裝置之第一裝置,其進一步包含:陽極;陰極;及安置於該陽極與該陰極之間的有機層,其中該有機層包含選自由下列組成之群之化合物:
- 如請求項7之裝置,其中該有機層係使用溶液加工來沈積。
- 如請求項7之裝置,其中該有機層為發射層且該式I化合物為主體。
- 如請求項9之裝置,其中該有機層進一步包含具有以下結構之發射性摻雜劑:
- 如請求項7之裝置,其中該第一裝置為消費型產品。
- 如請求項7之裝置,其中該第一裝置為有機發光裝置。
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2010
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- 2010-08-20 JP JP2013524828A patent/JP5770289B2/ja active Active
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- 2010-08-20 KR KR1020187008349A patent/KR102132102B1/ko active IP Right Grant
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US11316113B2 (en) | 2022-04-26 |
US20170170409A1 (en) | 2017-06-15 |
US9954180B2 (en) | 2018-04-24 |
JP2013536196A (ja) | 2013-09-19 |
DE112010005815T5 (de) | 2013-06-06 |
KR102132102B1 (ko) | 2020-07-09 |
TW201226407A (en) | 2012-07-01 |
US20220216421A1 (en) | 2022-07-07 |
JP5770289B2 (ja) | 2015-08-26 |
US20190081246A1 (en) | 2019-03-14 |
WO2012023947A1 (en) | 2012-02-23 |
DE112010005815B4 (de) | 2020-12-10 |
KR20130108265A (ko) | 2013-10-02 |
KR101753172B1 (ko) | 2017-07-04 |
KR20180033309A (ko) | 2018-04-02 |
US20130140549A1 (en) | 2013-06-06 |
US11289659B2 (en) | 2022-03-29 |
KR102004629B1 (ko) | 2019-07-26 |
KR20170076819A (ko) | 2017-07-04 |
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