CN106467452A - 有机材料及使用其的有机电激发光元件 - Google Patents
有机材料及使用其的有机电激发光元件 Download PDFInfo
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- CN106467452A CN106467452A CN201610626935.XA CN201610626935A CN106467452A CN 106467452 A CN106467452 A CN 106467452A CN 201610626935 A CN201610626935 A CN 201610626935A CN 106467452 A CN106467452 A CN 106467452A
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- 239000011368 organic material Substances 0.000 title claims abstract description 58
- 230000004888 barrier function Effects 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 239000002019 doping agent Substances 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims description 118
- 239000000203 mixture Substances 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 239000010409 thin film Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- -1 benzo fluorenyl Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 238000007725 thermal activation Methods 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000005540 biological transmission Effects 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000010408 film Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 1,2-dihydrophenazine Chemical compound C1=CC=C2N=C(C=CCC3)C3=NC2=C1 ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 0.000 claims description 4
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000027756 respiratory electron transport chain Effects 0.000 abstract description 17
- 230000005525 hole transport Effects 0.000 abstract description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 130
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 238000007872 degassing Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000006870 function Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000003111 delayed effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 230000005611 electricity Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 4
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical class C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 150000002220 fluorenes Chemical class 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 238000004776 molecular orbital Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UNEURVGVRYJOMG-UHFFFAOYSA-N (4-methoxynaphthalen-1-yl)boronic acid Chemical compound C1=CC=C2C(OC)=CC=C(B(O)O)C2=C1 UNEURVGVRYJOMG-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PKDVNRITKFAVFU-UHFFFAOYSA-N CC1(C=CC=C2C=C3C(C=C4C5=CC=CC=C5C5=CC=CC=C5C4=C3)=C12)C Chemical group CC1(C=CC=C2C=C3C(C=C4C5=CC=CC=C5C5=CC=CC=C5C4=C3)=C12)C PKDVNRITKFAVFU-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- LCSNDSFWVKMJCT-UHFFFAOYSA-N dicyclohexyl-(2-phenylphenyl)phosphane Chemical group C1CCCCC1P(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 LCSNDSFWVKMJCT-UHFFFAOYSA-N 0.000 description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- DXJPAROGPFPUHR-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)c1ccccc1-c1ccccc1.OB(O)c1ccccc1-c1ccccc1 DXJPAROGPFPUHR-UHFFFAOYSA-N 0.000 description 1
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 1
- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical group C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 description 1
- XURSAEHRFFSJED-UHFFFAOYSA-N 1-bromo-4-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=C(Br)C2=C1 XURSAEHRFFSJED-UHFFFAOYSA-N 0.000 description 1
- VJDLDUNBMSSGJU-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound COC1=CC=CC2=CC=CC=C12.COC1=CC=CC2=CC=CC=C12 VJDLDUNBMSSGJU-UHFFFAOYSA-N 0.000 description 1
- UBHOJJRMAHJLMR-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetrakis(3-methylphenyl)pyrene-1,6-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C3=CC=C4C=CC(=C5C=CC(C3=C54)=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 UBHOJJRMAHJLMR-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical group C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- UJCQCUHXXOYHGI-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1.ClC1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 UJCQCUHXXOYHGI-UHFFFAOYSA-N 0.000 description 1
- MSBVBOUOMVTWKE-UHFFFAOYSA-N 2-naphthalen-2-ylnaphthalene Chemical group C1=CC=CC2=CC(C3=CC4=CC=CC=C4C=C3)=CC=C21 MSBVBOUOMVTWKE-UHFFFAOYSA-N 0.000 description 1
- VLTZTMAUGMZPHK-UHFFFAOYSA-N 2-phenylaniline Chemical compound NC1=C(C=CC=C1)C1=CC=CC=C1.NC1=C(C=CC=C1)C1=CC=CC=C1 VLTZTMAUGMZPHK-UHFFFAOYSA-N 0.000 description 1
- RLPAWKJLZUFLCR-UHFFFAOYSA-N 4-(4-aminophenyl)-3-naphthalen-1-yl-n,n-diphenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC2=CC=CC=C12 RLPAWKJLZUFLCR-UHFFFAOYSA-N 0.000 description 1
- GQXFSXMUBDPXBG-UHFFFAOYSA-N 4-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=C2C=CC=C1Br GQXFSXMUBDPXBG-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
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- JNIYEWVAZVOUPJ-UHFFFAOYSA-N 4-propan-2-ylaniline Chemical compound C(C)(C)C1=CC=C(N)C=C1.C(C)(C)C1=CC=C(N)C=C1 JNIYEWVAZVOUPJ-UHFFFAOYSA-N 0.000 description 1
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- 230000035935 pregnancy Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
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- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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- 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
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- 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
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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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- 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
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- H05B33/00—Electroluminescent light sources
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- H05B33/00—Electroluminescent light sources
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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Abstract
本发明公开一种有机材料,其包括如式(A)所示的化合物,其中A表示具有二至三个环的经取代或未经取代的稠环碳氢单元,m表示0至10的整数,G、Rs、R1至R3的定义于本发明的内容中详述。前述有机材料可应用有机EL元件的发光层(发光主体或掺杂剂)、电洞阻挡层、电子阻挡层、电子传输层以及/或电洞传输层中,由此制备出具有良好效能的有机EL元件。本发明另公开一种包括前述有机材料的有机电激发光元件。
Description
技术领域
本发明涉及一种有机材料以及关于此化合物的有机电激发光(以下称为:“有机EL”)元件。具体而言,本发明关于一种包含式(A)化合物的有机材料,以及一种利用前述有机材料于发光层、电洞阻挡层、电子阻挡层、电子传输层以及/或电洞传输层中的有机电激发光元件及相关装置、平板等。
背景技术
有机电激发光(有机EL)是一种发光二极体(LED),其中发光层是由有机化合物制成的膜,其可在相对应的电流下发出光线。有机化合物的发光层夹设于两个电极之间。有机EL由于其高照明、低重量、超薄外形、自照明而无须背光、低功耗、宽视角、高对比、制造方法简单以及反应时间快速的特性而应用于平板显示器中。
第一次观察到有机材料电激发光的现象是在1950年代早期由安德列贝纳诺斯(Andre Bernanose)和同事在法国南锡大学(Nancy Université)进行的。纽约大学(NewYork University)的马丁蒲伯(Martin Pope)和其同事在1963年第一次在真空下于掺杂有并四苯的蒽的单一纯晶体上观察直流电(DC)电激发光。
第一个二极体元件在1987年由伊士曼柯达(Eastman Kodak)的邓青云(ChingW.Tang)和史蒂文凡斯莱克(Steven Van Slyke)所发表。所述元件使用具有分离设置的电洞传输层和电子传输层的双层结构,使得工作电压降低并且改进效率,引领当今时代的有机EL研究和元件生产。
典型地,有机EL是由位于两个电极之间的有机材料层构成,其包含有电洞传输层(hole transporting layer,HTL)、发光层(emitting layer,EML)、电子传输层(electrontransporting layer,ETL)。有机EL的基本机制涉及载子(carrier)的注入、载子的传输、重组以及形成激子(exciton)以发光。当外部电压施加到有机发光元件时,电子和电洞分别自阴极和阳极注入,电子将从阴极注入到最低未占用分子轨域(lowest unoccupiedmolecular orbital,LUMO)中,而电洞将从阳极注入到最高占用分子轨域(highestoccupied molecular orbital,HOMO)中。当电子与电洞在发光层中重组时,形成激子并且随后发光。当发光分子吸收能量而达到激发态时,依据电子和电洞的自旋组合,激子可呈单重态或三重态。75%的激子通过电子和电洞的重组形成而达到三重激发态。从三重态衰减是自旋禁阻(self forbidden)的。因此,萤光电激发光元件仅具有25%的内部量子效率(internal quantum efficiency)。相较于萤光电激发光元件,磷光有机EL元件利用自旋─轨域相互作用(spin-orbit interacttion)可促进单重态与三重态之间的系统间穿越(intersystem crossing),因而获得来自单重态和三重态两者的发光,且电激发光元件的内部量子效率自25%升至100%。自旋─轨域相互作用可通过诸如铱(iridium)、铑(rhodium)、铂(platinum)、钯(palladium)等的重原子(heavy atom)来完成,且可以从有机金属络合物中被激发的金属至配位基的电荷转移态(metal to ligand charge transfer,MLCT)观察到磷光转换(phosphorescent transition)的现象。
近年来,安达教授(Adachi)及其同事研发一种结合热活化型延迟萤光(thermallyactivated delayed fluorescence,TADF)机制的新型萤光有机EL元件,其是通过反向系统间穿越(reverse intersystem crossing,RISC)机制,将自旋禁阻的三重态激子转化至单重态能阶以获得激子形成的高效率的一种具有前景的方式。
三重态及单重态激子均能被磷光有机EL利用。由于与单重态激子相比,三重态激子具有较长的半衰期及扩散长度,磷光有机EL一般需要在发光层与电子传输层之间设置额外的电洞阻挡层(hole blocking layer,HBL)或需要在发光层与电洞传输层之间的电子阻挡层(electron blocking layer,EBL)。使用电洞阻挡层或电子阻挡层的目的是限制所注入的电洞及电子之间的重组,以及使位于发光层内产生的激子呈现松弛(relaxation),因而得以改进元件的效率。为了满足这些作用,电洞阻挡材料或电子阻挡材料必须具有适合用来阻断电洞或电子自发光层传输至电子传输层或至电洞传输层的HOMO与LUMO能阶。
对于能够有效传输电子或电洞且可阻挡电洞,又可具有良好热稳定性及高发光效率的有机EL材料的需求是持续存在的。根据上述的原因,本发明的目的在于解决现有技术的这些问题并提供热稳定性、高亮度以及长半衰期时间等方面都相当优异的有机EL元件。本发明揭露一种包括式(A)化合物的新颖有机材料,可用作发光主体或掺杂剂,或应用于电洞阻挡层、电子阻挡层、电子传输层、电洞传输层中,使元件具有良好的电荷载子移动性与优良的操作耐用性,能够降低驱动电压和功率消耗,并增进效率及半衰期时间。
发明内容
本发明提供一种新颖的有机材料,此材料可用作有机EL元件中的发光主体或掺杂剂,或应用于电洞阻挡层、电子阻挡层、电子传输层、电洞传输层等。使用前述有机材料的元件能够克服现有技术的材料的缺失,诸如短半衰期时间、低效率及高功率消耗。
本发明的一目的是提供一种有机材料,其可以用作有机EL元件中的电洞阻挡材料、电子阻挡材料等,或其它具有类似功能的材料。使用此材料可限定激子的转移途径,例如限定其转移至电子传输层、电洞传输层,或其它具有类似功能的层。
本发明的另一目的是提供一种有机材料,其可以用作有机EL元件中发光层的磷光主体材料、萤光主体材料、萤光掺杂剂材料等,或其它具有类似功能的材料。使用此材料可增进元件的效率及半衰期时间。
本发明的再一目的是提供一种有机材料,其可以用作有机EL元件中的电洞传输材料、电子传输材料等,或其它具有类似功能的材料。使用此材料可增进元件的半衰期时间、降低驱动电压及功率消耗。
本发明的又一目的是提供一种有机电激发光元件,其包括如下所述的化合物。本发明的有机电激发光元件可广泛地应用或设置于各种具备有机发光功能的有机发光装置(organic light emitting device),或者应用于发光平板(lighting panel)以及/或背光平板(backlight panel)中。
本发明在工业实践上具有经济优势。依据本发明,公开一种用于有机EL元件的有机材料,此有机材料包括如下式(A)所示的化合物:
其中A表示具有二至三个环的经取代或未经取代的稠环碳氢单元(fused ringhydrocarbon unit),m表示0至10的整数,G表示选自于由氢原子(hydrogen)、卤素(halide)、具有6至60个碳原子的经取代或未经取代的芳基(aryl group)以及具有3至60个碳原子的经取代或未经取代的杂芳基(heteroaryl group)所组成的群组,Rs表示氢原子、卤素或含碳取代基,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基(alkyl group)、具有6至30个碳原子的经取代或未经取代的芳基、具有6至30个碳原子的经取代或未经取代的芳烷基(aralkyl group)以及具有3至30个碳原子的经取代或未经取代的杂芳基所组成的群组。
较佳地,根据式(A)化合物,G可进一步表示选自于由氢原子、卤素、经取代或未经取代的苯基(phenyl group)、经取代或未经取代的芴基(fluorene group)、经取代或未经取代的苯并芴基(benzofluorene group)、经取代或未经取代的萘基(naphthyl group)、经取代或未经取代的蒽基(anthracenyl group)、经取代或未经取代的菲基(phenanthrenylgroup)、经取代或未经取代的芘基(pyrenyl group)、经取代或未经取代的屈基(chrysenylgroup)、经取代或未经取代的苯胺基(arylamine group)、经取代或未经取代的杂芳胺基(heteroarylamine group)、经取代或未经取代的咔唑基(carbazolyl group)、经取代或未经取代的双咔唑基(biscarbazolyl group)、经取代或未经取代的二苯并呋喃基(dibenzofuranyl group)、经取代或未经取代的二苯并噻吩基(dibenzothiophenylgroup)、经取代或未经取代的三嗪基(triazinyl group)、经取代或未经取代的二嗪基(diazinyl group)、经取代或未经取代的吡啶基(pyridinyl group)、经取代或未经取代的啡啉基(phenanthroline group)、经取代或未经取代二氢吖啶基(dihydroacridinegroup)、经取代或未经取代的吩噻嗪基(phenothiazine group)、经取代或未经取代的吩恶嗪基(phenoxazine group)以及经取代或未经取代的二氢吩嗪基(dihydrophenazinegroup)所组成的群组。
较佳地,前述含碳取代基可进一步表示选自于由烷基、芳基、芳烷基以及杂芳基所组成的群组,或者更佳地,可再进一步表示选自于具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基、具有6至30个碳原子的经取代或未经取代的芳烷基以及具有3至30个碳原子的经取代或未经取代的杂芳基所组成的群组。
本发明另公开一种有机电激发光元件,其包括一对电极、至少一发光层以及一个或多个有机薄膜层,其中电极由阴极和阳极所组成,发光层及有机薄膜层均设置于电极的阴极和阳极之间,且在发光层的至少一层或有机薄膜层的至少一层包括如前所述的有机材料,或者是发光层的至少一层以及有机薄膜层的至少一层均包括如前所述的有机材料。
较佳地,发光层可发出的光线包括红色、黄色、蓝色或绿色等的单一颜色的萤光或磷光,或至少二种以上颜色混合发出的萤光或磷光;在一更佳实施例中,发光层可发出的光线包括红色、黄色、蓝色或绿色等的单一颜色的热活化延迟萤光,或至少二种以上颜色混合发出的热活化延迟萤光。
较佳地,在发光层中所包含的前述有机材料可用以作为萤光主体材料(fluorescent host material)或磷光主体材料(phosphorescent host material);更佳地,亦可用以作为热活化延迟萤光主体材料(thermally activated delayedfluorescence host material)
较佳地,在发光层中所包含的前述有机材料可用作萤光掺杂剂材料(fluorescentdopant material);更佳地,可用作热活化延迟萤光掺杂剂材料(thermally activateddelayed fluorescence dopant material)。
较佳地,在发光层中所包含的前述有机材料亦可用作萤光掺杂剂材料(fluorescent dopant material);更佳地,可用作热活化延迟萤光掺杂剂材料(thermallyactivated delayed fluorescence dopant material)。
较佳地,在有机薄膜层中所包含的前述有机材料可用作电洞阻挡材料(holeblocking material)、电子阻挡材料(electron blocking material)、电洞传输材料(holetransporting material)、电子传输材料(electron transporting material),或其他具有类似于一种以上前述功能的材料。
本发明再公开一种发光装置(lighting device),其包括如前所述的有机电激发光元件。
本发明又公开一种发光平板(lighting panel),其包括如前所述的有机电激发光元件。
本发明又再公开一种背光平板(backlight panel),其包括如前所述的有机电激发光元件。
附图说明
图1显示本发明的有机EL元件的一实施例的示意图;
图2显示本发明的有机EL元件的一实施例的示意图;
图3显示本发明的有机EL元件的一实施例的示意图;
附图符号说明:
6透明电极,7电洞注入层,8电洞传输层,9发光层,10电子传输层,11电子注入层,12金属电极,13电洞阻挡层,13a电子阻挡层,13b电子阻挡层,14b电洞阻挡层。
具体实施方式
本发明欲探究的是一种有机材料以及一种使用此有机材料的有机EL元件。在下文中将提供生产、结构以及要素的详细描述以充分理解本发明。明显地是,本发明的应用不限于所属技术领域技术人员所熟悉的特定细节。另一方面,已知的常见要素和程序并未详细描述于本发明中,且不应对本发明产生不必要的限制。现将在下文中更详细地描述本发明的一些较佳实施例。但是,应认识到本发明可以在除了明确描述的实施例之外的多种其它实施例中广泛实践,即,本发明还可以广泛应用于其它实施例,并且除了如权利要求中所指定外,本发明的范围不受明确限制。
本发明涉及一种有机材料,其包括如式(A)所示的化合物,此有机材料可以用作有机EL元件的发光层中的发光层的磷光主体材料、萤光主体材料、萤光掺杂剂材料,或可作为用于电洞阻挡层、电子阻挡层、电动传输层、电子传输层的有机材料。在一较佳实施例中,前述有机材料实质上由如式(A)所示的化合物所构成。式(A)化合物的结构如下所示:
其中A表示具有二至三个环的经取代或未经取代的稠环碳氢单元,m表示0至10的整数,G表示选自于由氢原子、卤素、具有6至60个碳原子的经取代或未经取代的芳基以及具有3至60个碳原子的经取代或未经取代的杂芳基所组成的群组。Rs表示氢原子、卤素或含碳取代基,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基、具有6至30个碳原子的经取代或未经取代的芳烷基以及具有3至30个碳原子的经取代或未经取代的杂芳基所组成的群组。
在一较佳实施例中,根据上文提及的式(A)化合物,G可表示为经取代或未经取代的苯基、经取代或未经取代的萘基、经取代或未经取代的联苯基、经取代或未经取代的咔唑基、经取代或未经取代的双咔唑基、经取代或未经取代的二苯呋喃基、经取代或未经取代的二苯噻吩基、经取代或未经取代的三嗪基、经取代或未经取代的二嗪基、经取代或未经取代的吡啶基、经取代或未经取代的啡啉基、经取代或未经取代的二氢吖啶基、经取代或未经取代的吩噻嗪基、经取代或未经取代的吩恶嗪基、经取代或未经取代的二氢吩嗪基。
在一较佳实施例中,根据上文提及的式(A)化合物,G可表示为下列通式所示结构中的其中一种:
在一较佳实施例中,根据上文提及的式(A)化合物,其可进一步具有下列式(1)至式(9)所示结构中的其中一种:
其中m表示0至10的整数,G表示选自于由氢原子、卤素、具有6至60个碳原子的经取代或未经取代的芳基以及具有3至60个碳原子的经取代或未经取代的杂芳基所组成的群组。Rs表示氢原子、卤素或含碳取代基,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基、具有6至30个碳原子的经取代或未经取代的芳烷基以及具有3至30个碳原子的经取代或未经取代的杂芳基所组成的群组。
在一较佳实施例中,根据前述式(1)至式(9)所示的化合物,式中的G可进一步由下列通式所示结构中的其中一种所表示:
在一些较佳实施例中,本发明所述的化合物可选自于下列通式所示结构所组成的群组中的其中一种:
另一方面,本发明涉及一种有机电激发光元件,其可包括一对由阴极和阳极所组成的电极、至少一发光层以及一个或多个有机薄膜层,发光层及有机薄膜层均设置于所述对电极的阴极和阳极之间,且发光层的至少一层或有机薄膜层的至少一层包含有本发明的有机材料,或者是发光层的至少一层以及有机薄膜层的至少一层均包括本发明的有机材料。
图1至图3分别为本发明的有机电激发光元件的实施例的结构示意图。请参阅图1所示,在一较佳实施例中,此种有机电激发光元件的可包括透明电极6、电洞注入层7、电洞传输层8、发光层9、电子传输层10、电子注入层11以及金属电极12,并且进一步包括电洞阻挡层13。在此元件中,电洞注入层7设置于透明电极6与金属电极12之间,电洞传输层8设置于电洞注入层7与金属电极12之间,发光层9设置于电洞传输层8与金属电极12之间,电子传输层10设置于发光层9与金属电极12之间,电子注入层11设置于电子传输层10与金属电极12之间,而电洞阻挡层13则设置于发光层9与电子传输层10之间。
请参阅图2所示,在另一较佳实施例中,前述有机电激发光元件可依据需求省略电洞阻挡层的设置,并且进一步包括电子阻挡层13a,电子阻挡层13a设置于电洞传输层8与发光层9之间。
请参阅图3所示,在又一较佳实施例中,前述有机电激发光元件可依据需求,同时包括电子阻挡层及电洞阻挡层,且电子阻挡层13b设置于电洞传输层8与发光层9之间,电洞阻挡层14b设置于发光层9与电子传输层10之间。
此外,前述发光层9可发出磷光、萤光,或其它可经有机材料电性激发产生的光线;在一更佳实施例中,自发光层9所发出的萤光可以是热活化延迟萤光。
在一较佳实施例中,前述有机电激发光元件的发光层可发出的光线包括红色、黄色、蓝色或绿色等的单一颜色的萤光或磷光,或至少二种以上颜色混合发出的萤光或磷光;在一更佳实施例中,发光层可发出的光线包括红色、黄色、蓝色或绿色等的单一颜色的热活化延迟萤光,或至少二种以上颜色混合发出的热活化延迟萤光。
在一较佳实施例中,发光层中所包含的前述有机材料亦可用以作为萤光主体材料(fluorescent host material)或磷光主体材料(phosphorescent host material);在一更佳实施例中,发光层中所包含的前述有机材料亦可用以作为热活化延迟萤光主体材料(thermally activated delayed fluorescence host material)。
在一较佳实施例中,在发光层中所包含的前述有机材料亦可用作萤光掺杂剂材料(fluorescent dopant material);在一更佳实施例中,可用作热活化延迟萤光掺杂剂材料(thermally activated delayed fluorescence dopant material)。
在一较佳实施例中,在有机薄膜层中所包含的前述有机材料可用作电洞阻挡材料(hole blocking material)、电子阻挡材料(electron blocking material)、电洞传输材料(hole transporting material)、电子传输材料(electron transporting material),或其他具有类似于一种以上前述功能的材料。
本发明所述的有机材料,其详细制备可以通过例示性实施例阐明,但不限于例示性实施例。实例1至5显示本发明中的衍生物的一些实例的制备。实例6至8显示有机EL元件的制造和有机EL元件测试报告的I-V-B、半衰期时间。
实例1:化合物EX1的合成
合成1-溴-4-甲氧基萘(1-bromo-4-methoxynaphthalene)
将50g(316mmol)1-甲氧基萘(1-methoxynaphthalene)以及600mL乙腈(acetonitrile)添加至反应槽(reaction vessel)中,然后在加冰冷藏(ice-cooled)的环境下,添加62g(348mmol)N-溴代丁二醯亚胺(N-bromosuccinimide)形成混合物。将混合物搅拌6小时后,留置一晚以进行反应。将2000mL水添加于反应后的混合物中,再利用二氯甲烷和水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥以去除溶剂,形成残余物,通过以硅胶填充的管柱层析来纯化残余物,得到50.9g(215mmol)产物,产率为68%。
合成4-甲氧基萘-1-基硼酸(4-methoxynaphthalen-1-ylboronic acid)
取162mL(258mmol)过量的含有1.6M丁基锂(n-BuLi)的己烷溶液,并且-78℃的氮气环境下,将前述溶液在-78℃的氮气环境下添加于含有1-溴-4-甲氧基萘(50.9g,215mmol)的无水四氢呋喃(dry tetrahydrofuran)溶液,形成混合物。将混合物置于0℃环境下1小时,冷却至-78℃,再将35g(335mmol)硼酸三甲酯(tri-methylborate)滴加于冷却后的混合物。将混合物缓慢加温至室温,搅拌24小时;再将250mL的2N氢氯酸(HCl)溶液加入混合物中,搅拌1小时,以进行反应。将反应后的混合物利用乙酸乙酯和水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥以去除溶剂,形成残余物,通过己烷对残余物进行结晶(crystallation),得到31.8g(157mmol)呈白色固体状的4-甲氧基萘-1-基硼酸,产率为61%。
合成2-(4-甲氧基萘-1-基)苯甲酸甲酯(methyl 2-(4-methoxynaphthal-en-1-yl)benzoate)
将26.8g(157mmol)2-氯苯甲酸甲酯(methyl 2-chlorobenzoate)、31.8g(157mmol)4-甲氧基萘-1-基硼酸、3.5g(3mmol)四(三苯基膦)钯(tetra-kis(triphenylphosphine)palladium,Pd(PPh3)4)、157mL 2M碳酸钠(Na2CO3)、200mL乙醇(EtOH)以及400mL甲苯(toluene)的混合物经过脱气处理并且放置在氮气下,随后在100℃下加热12小时进行反应。反应完成后的混合物随后冷却至室温,再利用乙酸乙酯和水萃取出有机层。将有机层用无水硫酸镁干燥以去除溶剂,形成残余物,并且通过以硅胶填充的管柱层析来纯化残余物,得到26.6g(91mmol)呈白色固体状的产物,产率为58%。
合成2-(2-(4-甲氧基萘-1-基)苯基)丙-2-醇(methyl 2-(2-(4-methoxy-naphthalen-1-yl)phenyl)propan-2-ol)
将26.6g(91mmol)2-(4-甲氧基萘-1-基)苯甲酸甲酯置于锥形瓶(flask)中,再将锥形瓶内处理成真空状态并且填充氮气,随后将700mL四氢呋喃添加于瓶内,在-78℃的环境下搅拌10分钟。接着,将含有284mL(455mol)的1.6M甲基锂(MeLi)/己烷混合溶液添加于其中,在-78℃的环境下搅拌10分钟,然后在室温下搅拌6小时进行反应。反应中止后,将反应后的混合物利用乙酸乙酯和蒸馏水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥,并且利用旋转蒸发器(rotary evaporator)移除溶剂,形成残余物,通过由己烷和乙酸乙酯作为展开剂(developing solvent)对残余物进行层析,得到20.7g 2-(2-(4-甲氧基萘-1-基)苯基)丙-2-醇,产率为78%。
合成5-甲氧基-7,7-二甲基-7H-苯并[c]芴(5-methoxy-7,7-dimethyl-7H-benzo[c]fluorene)
将20.7g(70.8mmol)2-(2-(4-甲氧基萘-1-基)苯基)丙-2-醇置于锥形瓶中,再将锥形瓶内处理成真空状态并且填充氮气,随后将200mL醋酸(AcOH)添加于瓶内,在0℃的环境下搅拌10分钟。接着,将400mL的磷酸(phosphoric acid,H3PO4)添加于其中,在室温下搅拌3小时进行反应。反应中止后,将反应后的混合物先以氢氧化纳中和,再利用乙酸乙酯和蒸馏水萃取出有机层。将萃取出的有机层用无水硫酸镁进行干燥后,利用旋转蒸发器移除溶剂,形成残余物,通过由己烷和乙酸乙酯作为展开剂对残余物进行层析,得到16.7g 5-甲氧基-7,7-二甲基-7H-苯并[c]芴,产率为86%。
合成9-溴-5-甲氧基-7,7-二甲基-7H-苯并[c]芴(9-bromo-5-methoxy-7,7-dimethyl-7H-benzo[c]fluorene)
将16.7g(60.9mmol)5-甲氧基-7,7-二甲基-7H-苯并[c]芴置于锥形瓶中,再将锥形瓶内处理成真空状态并且填充氮气,随后将340mL四氢呋喃(tetrahydrofuran)添加于瓶内,在0℃的环境下搅拌10分钟。接着,将11.9g(67mmol)的N-溴代丁二酰亚胺(N-bromosuccinimide,NBS)添加于其中,在室温下搅拌30分钟进行反应。反应中止后,将反应后的混合物利用乙酸乙酯和蒸馏水萃取出有机层。将萃取出的有机层用无水硫酸镁进行干燥后,利用旋转蒸发器移除溶剂,形成残余物,通过由己烷和乙酸乙酯作为展开剂对残余物进行层析,得到18g 9-溴-5-甲氧基-7,7-二甲基-7H-苯并[c]芴,产率为84%。
合成9-(联苯-2-基)-5-甲氧基-7,7-二甲基-7H-苯并[c]芴(9-(biphenyl-2-yl)-5-methoxy-7,7-dimethyl-7H-benzo[c]fluorene)
将35.3g(100mmol)9-溴-5-甲氧基-7,7-二甲基-7H-苯并[c]芴、21.8g(110mmol)联苯-2-基硼酸(biphenyl-2-ylboronic acid)、2.31g(2mmol)四(三苯基膦)钯、75mL 2M碳酸钠(Na2CO3)、150mL乙醇和300mL甲苯的混合物经过脱气处理并且放置在氮气下,随后在100℃下加热12小时。将反应完成后的混合物冷却至室温,再利用乙酸乙酯和水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥以去除溶剂,形成残余物。通过以硅胶填充的管柱层析来纯化残余物,得到31.1g(73.0mmol)呈白色固体状的产物,产率为73%。
合成中间体I(intermediate I)
在经过脱气处理及填充氮气的3000mL三颈烧瓶中,将25.6g(60mmol)9-(联苯-2-基)-5-甲氧基-7,7-二甲基-7H-苯并[c]芴溶解于无水二氯甲烷(1500mL)中,随后再添加97.5g(600mmol)氯化铁(III)(Iron(III)chloride)形成混合物,搅拌混合物1小时,在搅拌后的混合物中添加500mL甲醇并且分离出有机层。在真空中将有机层去除溶剂,形成残余物,通过以硅胶填充的管柱层析(己烷-二氯甲烷)来纯化残余物,得到15.5g(36.6mmol)呈白色固体状的产物,产率为61%。
合成中间体II(intermediate II)
将4.9g(11.6mmol)中间体I与13.4g(1168mmol)盐酸吡啶(pyridinehydrochloride)的混合物经过脱气处理并且放置在氮气下,随后在220℃下加热6小时以进行反应。反应完成后的混合物随后冷却至室温后,并且添加水,形成固状物。之后将固状物进行过滤、用水清洗,以及在高真空(high vacuum)环境下进行干燥,以获得4.4g(10.8mmol)产物,产率93%。
合成中间体III
在经过脱气处理及填充氮气的1000mL三颈烧瓶中,将4.1g(10mmol)中间体II溶解于无水二氯甲烷(660mL)中,随后再添加20mmol吡啶(pyridine)形成混合物,再将混合物冷却于冰盐浴(ice salt bath)中。将含有6.8mL(40mmol)三氟甲磺酸酐(trifluoromethanesulfonic anhydride)的40mL二氯甲烷溶液在氮气环境下逐滴添加于混合物中,反应进行6小时,而后加入甲醇及水以进行淬火(quench),形成固状物。对固状物进行过滤并且用水、甲醇及二氯甲烷洗出残余物,再利用甲苯对残余物进行再结晶,以获得4.0g(7.4mmol)的产物,产率74%。1H NMR(CDCl3,400MHz):化学位移(ppm)9.55(s,1H),9.07(d,J=8.0Hz,1H),8.72(d,J=8.0Hz,1H),8.77~8.74(m,2H),8.71~8.66(m,2H),8.22(d,J=8.0Hz,1H),7.91~7.63(m,7H),1.71(m,6H).
合成中间体IV
将3.7g(6.8mmol)中间体III、7g(27.2mmol)双联频哪醇硼酸酯(bis(pinacolato)diboron)、0.36g(0.31mmol)四(三苯基膦)钯、4g(40.56mmol)醋酸钾(potassium acetate)和200mL1,4-二恶烷(1,4-dioxane)的混合物经过脱气处理并且放置在氮气下,随后在120℃下加热24小时。将反应完成后的混合物冷却至室温,再利用乙酸乙酯和水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥以去除溶剂,形成残余物。使用己烷及乙酸乙酯作为冲提液(eluent),通过管柱层析来纯化残余物,得2.4g呈淡黄色的产物,产率为67%。
合成化合物EX1
将2.0g(3.8mmol)中间体IV、1.9g(4.2mmol)9-(4-溴苯基)-10(萘-1-基)蒽(9-(4-bromophenyl)-10-(naphthalen-1-yl)anthracene)、0.11g(0.1mmol)四(三苯基膦)钯、5mL2M碳酸钠、10mL乙醇和20mL甲苯的混合物经过脱气处理并且放置在氮气下,随后在100℃下加热过夜。将反应完成后的混合物冷却至室温,再利用100mL乙酸乙酯和200mL水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥,在减压环境下蒸散溶剂,形成残余物。通过硅胶填充的管柱层析(Hx~EA)来纯化残余物,得到1.7g产物,产率为57%。MS(m/z,FAB+):772.2.
实例2:化合物EX13的合成
合成双(4-异丙苯基)胺(bis(4-isopropylphenyl)amine)
将10g(50mmol)1-溴-4-异丙苯(1-bromo-4-isopropylbenzene)、7.4g(55mmol)4-异丙苯胺(4-isopropylaniline)、0.25g(1mmol)乙酸钯(II)(palla-dium(II)acetate)、0.75g(2.0mmol)2-(二环己基膦基)联苯(2-(dicyclohexyl-phosphino)biphenyl)、9.6g(100mmol)叔丁醇钠(sodium tert-butoxide)与100mL邻二甲苯(o-xylene)的混合物在氮气环境下进行回流(reflux),随后在100℃下进行过滤,收集滤液(filtrate)。将滤液添加于1L甲醇中同时进行搅拌,形成沉淀物,再对沉淀物进行抽滤(suction)。利用己烷对抽滤后的沉淀物进行再结晶,以获得成4.7g呈黄色状的产物,产率37%。
合成化合物EX2
将3.2g(6mmol)中间体III、1.5g(6mmol)双(4-异丙苯基)胺、0.1g(0.4mmol)乙酸钯(II)、0.48g 2,2'-双二苯膦基-1,1'-联萘(2,2'-bis(diphenyl-phosphino)-1,1'-binaphthyl,BINAP)、4g碳酸钾(potassium carbonate)和50mL甲苯的混合物经过脱气处理并且放置在氮气下,随后在110℃下加热过夜进行反应。将反应完成后的混合物冷却至室温,添加200mL甲醇于混合物中同时搅拌,形成沉淀物,再对沉淀物进行抽滤。利用乙酸乙酯对抽滤后的沉淀物进行再结晶,以获得2.3g呈黄色状的产物,产率61%。MS(m/z,FAB+):645.6.
实例3:化合物EX23的合成
合成N-(联苯-2-基)-9,9'-螺二[芴]-4-胺(N-(biphenyl-2-yl)-9,9'-spiro-bi[fluoren]-4-amine)
将19.8g(50mmol)4-溴-9,9'-螺二[芴](4-bromo-9,9'-spirobi[fluor-ene])、9.3g(55mmol)联苯-2-胺(biphenyl-2-amine)、0.25g(1mmol)乙酸钯(II)、0.75g(2.0mmol)2-(二环己基膦基)联苯、9.6g(100mmol)叔丁醇钠以及100mL邻二甲苯的混合物在氮气环境下回流过夜以进行反应。将反应完成后的混合物置于100℃下进行过滤,收集滤液。将滤液添加至1L甲醇同时搅拌,形成沉淀物,再对沉淀物进行抽滤。利用己烷对抽滤后的沉淀物进行再结晶,以获得12.3g呈黄色的产物,产率51%。
合成化合物EX3
将3.2g(6mmol)中间体III、2.9g(6mmol)N-(联苯-2-基)-9,9'-螺二[芴]-4-胺、0.1g(0.4mmol)乙酸钯(II)、0.48g 2,2'-双二苯膦基-1,1'-联萘、4g碳酸钾与50mL甲苯的混合物在氮气环境经过脱气处理并且放置在氮气下,随后在110℃下加热过夜进行反应。将反应完成后的混合物冷却至室温,随后添加200mL甲醇同时搅拌,形成沉淀物,再对沉淀物进行抽滤。利用乙酸乙酯对抽滤后的沉淀物进行再结晶,以获得1.9g呈黄色的产物,产率37%。MS(m/z,FAB+):875.6.
实例4:化合物EX26的合成
合成化合物EX26
将2.0g(3.8mmol)中间体IV、1.1g(4.2mmol)2-氯-4,6-二苯基-1,3,5-三嗪(2-chloro-4,6-diphenyl-1,3,5-triazine)、0.11g(0.1mmol)四(三苯基膦)钯、5mL 2M碳酸钠、10mL乙醇与20mL甲苯的混合物经过脱气处理并放置在氮气下,随后在100℃下加热过夜进行反应。将反应完成后的混合物冷却至室温,再利用100mL乙酸乙酯和200mL水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥,在减压环境下蒸散溶剂,形成残余物。通过管柱层析(Hx~EA)来纯化残余物,得到1.7g产物,产率为71%。MS(m/z,FAB+):625.2.
实例5:化合物EX30的合成
合成化合物EX30
将2.0g(3.8mmol)中间体IV、1.2g(4.2mmol)2-氯-9-苯基-1,10-啡啉(2-chloro-9-phenyl-1,10-phenanthroline)、0.11g(0.1mmol)四(三苯基膦)钯、5mL 2M碳酸钠、10mL乙醇与20mL甲苯的混合物经过脱气处理并放置在氮气下,随后在100℃下加热过夜进行反应。将反应完成后的混合物冷却至室温,再利用100mL乙酸乙酯和200mL水萃取出有机层,并且将萃取出的有机层用无水硫酸镁进行干燥,在减压环境下蒸散溶剂,形成残余物。利用二氯甲烷对残余物进行再结晶,得到2g产物,产率为83%。MS(m/z,FAB+):648.1.
产生有机EL元件的一般方法
依据本发明,提供一种经铟锡氧化物(indium tin oxide,ITO)涂布的玻璃(下文ITO基材),其电阻为9欧姆/平方(ohm/square)至12欧姆/平方且厚度为120nm到160nm,并且在超声波浴中利用多个清洁步骤(例如:清洁剂、去离子水)进行清洁。在进行有机层的气相沉积过程之前,通过UV和臭氧进一步处理经清洁后的ITO基材。用ITO基材的所有前处理过程均于洁净室(100级)环境中进行。
在诸如电阻加热石英舟(resistively heated quartz boats)等的高真空单元(10-7托)中,通过气相沉积将这些有机层依序涂布于ITO基材上。通过石英晶体监控器(quartz-crystal monitor)精确监控或设定对应层的厚度以及气相沉积速率(0.1nm/sec至0.3nm/sec)。如上所述,个别层还可能由一种以上化合物所组成,意即一般来说掺杂有掺杂剂材料的主体材料。这类型材料可透过从两种或两种以上来源进行共气化(co-vaporization)而达成。
更具体的是,于一较佳实施例中,在本发明所述的有机EL元件中,二吡嗪并[2,3-f:2,3-]喹喔啉-2,3,6,7,10,11-六甲腈(Dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile,HAT-CN)可用作电洞注入材料,N,N-双(萘-1-基)-N,N-双(苯基)-联苯胺(N,N-bis(naphthalene-1-yl)-N,N-bis(phenyl)-benzidine,NPB)最常用于电洞传输材料,N-(联苯-4-基)-9,9-二甲基-N-(4'-苯基联苯-4-基)-9H-芴-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4'-phenylbiphenyl-4-yl)-9H-fluoren-2-amine)(以下称为EB2)可用于电子阻挡材料,10,10-二甲基-12-(4-(芘-1-基)苯基)-10H-茚并[1,2-b]三亚苯(10,10-dimethyl-12-(4-(pyren-1-yl)phenyl)-10H-indeno[1,2-b]triphenylene,)(以下称为PT-312)可用于蓝色发光主体材料,N1,N1,N6,N6-四甲苯基芘-1,6-二胺(N1,N1,N6,N6-tetram-tolylpyrene-1,6-diamine)(以下称为D1)可用于蓝色发光客体材料,2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-13-基)-9-苯基-1,10-啡啉(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-13-yl)-9-phenyl-1,10-phenanthroline)可用于电子传输材料(以下以ET1称之)并且可与5%锂金属(Li)共沉积,2-(10,10-二甲基-10H-茚并[2,1-b]三亚苯-12-基)-4,6-二苯基-1,3,5-三嗪(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,6-diphenyl-1,3,5-triazine)可用于电子传输材料(以下以ET2称之)并且可与8-羟基喹啉-锂(8-hydroxyquinolato-lithium,LiQ),双(2-甲基-8-羟基喹啉)-4-(苯基苯酚)铝(Bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium,BAlq)可用于电洞阻挡材料(HBM)以及/或磷光主体材料,双(2-苯基吡啶)(2,4-二苯基吡啶)铱(III)(Bis(2-phenyl-pyridinato)(2,4-diphenylpyridinato)iridium(III))可用于磷光掺杂剂(以下称为D2),上述可用于产生标准有机EL元件控制组的现有技术的OLED材料和本发明中的比较性材料,如以下化学结构所示:
典型的有机EL元件由诸如含有Al、Mg、Ca、Li、K的低功函数金属材料所构成,并通过热蒸镀作为阴极,低功函数金属材料可辅助电子从阴极注入至电子传输层。此外,为了减少电子注入的屏障,并且改进有机EL元件性能,在阴极与电子传输层之间引入薄膜电子注入层。电子注入层的常规材料是具有低功函数的金属卤化物或金属氧化物,例如:LiF、LiQ、MgO或Li2O。另一方面,在有机EL元件制造之后,通过使用PR650光谱扫描光谱仪(PR650spectra scan spectrometer)测量EL光谱(EL spectra)和CIE座标(CIEcoordination)。此外,用吉时利2400可程式设计电压-电流源(Keithley2400programmable voltage-current source)获得电流/电压、发光/电压以及良率/电压的特性资料。上述设备是于室温(约25℃)及大气压力环境中操作。
实例6
使用类似于上述一般方法的程序,产生具有以下元件结构I的蓝色萤光有机EL元件,元件结构:ITO/HAT-CN(10nm)/NPB(800nm)/电子阻挡材料(EBM)(5nm)/掺杂5%掺杂剂的蓝色发光主体PT-312(30nm)/共沉积5%Li的ET1(40nm)/Al(160nm)。蓝光萤光有机EL元件测试报告的I-V-B(1000尼特(nit)下)和半衰期时间如表1所示。半衰期时间被定义为1000cd/m2的初始亮度降到一半的时间。
表1
实例7
使用类似于上述一般方法的程序,产生具有以下元件结构II的蓝色萤光有机EL元件,元件结构II:ITO/HAT-CN(10nm)/NPB(800nm)/掺杂5%D1的PT-312(30nm)/HBM(5nm)/掺杂5%Li的电子传输材料(ETM)/Al(160nm)。蓝色萤光有机EL元件测试报告的I-V-B(1000尼特(nit)下)和半衰期时间如表2所示。半衰期时间被定义为1000cd/m2的初始亮度降到一半的时间。
表2
ETM | HBM | 电压(V) | 效率(cd/A) | CIE(y) | 半衰期时间(小时) |
ET1 | ET2 | 4.5 | 5.5 | 0.175 | 250 |
ET1 | EX30 | 4.5 | 5.6 | 0.176 | 290 |
EX26 | ET2 | 4.7 | 5.8 | 0.178 | 280 |
EX26 | -- | 5.0 | 5.1 | 0.183 | 160 |
实例8
使用类似于上述一般方法的程序,产生具有以下元件结构III的磷光有机EL元件,元件结构III:ITO/HAT-CN(10nm)/NPB(800nm)/EBM(5nm)/添加15%D2的磷光主体(PHhost)(30nm)/HBM(10nm)/共沉积50%LiQ的ET2(35nm)/LiQ(5nm)/Al(160nm)。磷光有机EL元件测试报告的I-V-B(1000尼特(nit)下)和半衰期时间如表3所示。半衰期时间被定义为3000cd/m2的初始亮度降到一半的时间。
表3
PHhost | HBM | 电压(V) | 效率(cd/A) | CIE(y) | 半衰期时间(小时) |
BAlq | ET2 | 5.8 | 29 | 0.45,0.56 | 250 |
EX39 | ET2 | 4.3 | 36 | 0.43,0.59 | 290 |
EX39 | EX30 | 3.8 | 35 | 0.43,0.59 | 280 |
EX39 | -- | 4.0 | 32 | 0.43,0.59 | 160 |
请参见表1、表2及表3所示,在以上有机EL元件测试报告的较佳实施例中,显示使用本发明含有式(A)化合物的有机材料应用于有机EL元件的发光主体材料、发光掺杂剂材料、电洞阻挡层材料、电子阻挡层材料、电子传输层材料以及电洞传输层材料中,与现有技术的OLED材料相较之下,可使元件达到较为良好的性能。
总而言之,本发明公开一种有机材料,其可以用于有机EL元件中。本发明亦公开一种有机EL元件,可采用前述有机材料作为有机EL元件中的发光主体材料、发光掺杂剂材料、电洞阻挡层材料、电子阻挡层材料、电子传输层材料以及电洞传输层材料,或其他具有替代性功能的材料。所述的有机材料具有由下列式(A)表示的化合物:
其中A表示具有二至三个环的经取代或未经取代的稠环碳氢单元,m表示0至10的整数,G表示选自于由氢原子、卤素、具有6至60个碳原子的经取代或未经取代的芳基以及具有3至60个碳原子的经取代或未经取代的杂芳基所组成的群组。Rs表示氢原子、卤素或含碳取代基,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基、具有6至30个碳原子的经取代或未经取代的芳烷基以及具有3至30个碳原子的经取代或未经取代的杂芳基所组成的群组。
以上所述仅是本发明的较佳实施例而已,并非对本发明有任何形式上的限制,虽然本发明已以较佳实施例公开如上,然而并非用以限定本发明,任何所属技术领域技术人员在不脱离本发明技术方案的范围内,当可利用上述公开的技术内容做出些许更动或修饰等同变化的等效实施例,但凡是未脱离本发明技术方案的内容,依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰,均仍属于本发明技术方案的范围内。
Claims (17)
1.一种化合物,其具有以下式(A)所示的结构:
其中A表示具有二至三个环的经取代或未经取代的稠环碳氢单元,m表示0至10的整数,G表示选自于由氢原子、卤素、具有6至60个碳原子的经取代或未经取代的芳基以及具有3至60个碳原子的经取代或未经取代的杂芳基所组成的群组;Rs表示氢原子、卤素或含碳取代基,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基、具有6至30个碳原子的经取代或未经取代的芳烷基以及具有3至30个碳原子的经取代或未经取代的杂芳基所组成的群组。
2.根据权利要求1所述的化合物,其中G表示选自于由氢原子、卤素、经取代或未经取代的苯基、经取代或未经取代的芴基、经取代或未经取代的苯并芴基、经取代或未经取代的萘基、经取代或未经取代的蒽基、经取代或未经取代的菲基、经取代或未经取代的芘基、经取代或未经取代的屈基、经取代或未经取代的苯胺基、经取代或未经取代的杂芳胺基、经取代或未经取代的咔唑基、经取代或未经取代的双咔唑基、经取代或未经取代的二苯并呋喃基、经取代或未经取代的二苯并噻吩基、经取代或未经取代的三嗪基、经取代或未经取代的二嗪基、经取代或未经取代的吡啶基、经取代或未经取代的啡啉基、经取代或未经取代二氢吖啶基、经取代或未经取代的吩噻嗪基、经取代或未经取代的吩恶嗪基以及经取代或未经取代的二氢吩嗪基所组成的群组。
3.根据权利要求1所述的化合物,其中G具有选自于下列所示结构所组成的群组中的一种:
4.根据权利要求1所述的化合物,其进一步具有下列式(1)至式(9)所示结构中的其中一种:
其中m表示0至10的整数,G表示选自于由氢原子、卤素、具有6至30个碳原子的经取代或未经取代的芳基以及具有3至60个碳原子的经取代或未经取代的杂芳基所组成的群组,Rs表示氢原子、卤素或含碳取代基,R1至R3独立地表示选自于由氢原子、卤素、具有1至30个碳原子的经取代或未经取代的烷基、具有6至30个碳原子的经取代或未经取代的芳基、具有6至30个碳原子的经取代或未经取代的芳烷基以及具有3至30个碳原子的经取代或未经取代的杂芳基所组成的群组。
5.根据权利要求3所述的有机材料,其中式(1)至(9)中的G具有选自于下列所示结构所组成的群组中的一种:
6.一种有机电激发光元件,其包括一对电极、至少一发光层以及一个或多个有机薄膜层,其中所述对电极由阴极和阳极所组成,所述至少一发光层以及所述一个或多个有机薄膜层设置于所述对电极的阴极和阳极之间,且所述至少一发光层或所述一个或多个有机薄膜层包括一种如权利要求1至4中任一项所述的有机材料。
7.根据权利要求6所述的有机电激发光元件,其中所述至少一发光层包括所述有机材料,且所述有机材料为萤光主体材料或磷光主体材料。
8.根据权利要求7所述的有机电激发光元件,其中所述至少一发光层包括所述有机材料,且所述有机材料为热活化延迟萤光主体材料。
9.根据权利要求6所述的有机电激发光元件,其中所述至少一发光层包括所述有机材料,且所述有机材料为萤光掺杂剂材料。
10.根据权利要求9所述的有机电激发光元件,其中所述至少一发光层包括所述有机材料,且所述有机材料为热活化延迟萤光掺杂剂材料。
11.根据权利要求6所述的有机电激发光元件,其中所述一个或多个有机薄膜层包括所述有机材料,且所述有机材料为电洞阻挡材料。
12.根据权利要求6所述的有机电激发光元件,其中所述一个或多个有机薄膜层包括所述有机材料,且所述有机材料为电子阻挡材料。
13.根据权利要求6所述的有机电激发光元件,其中所述一个或多个有机薄膜层包括所述有机材料,且所述有机材料为电洞传输材料。
14.根据权利要求6所述的有机电激发光元件,其中所述一个或多个有机薄膜层包括所述有机材料,且所述有机材料为电子传输材料。
15.一种发光装置,其包括如权利要求6至14中任一项所述的有机电激发光元件。
16.一种发光平板,其包括如权利要求6至14中任一项所述的有机电激发光元件。
17.一种背光平板,其包括如权利要求6至14中任一项所述的有机电激发光元件。
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