CN115440903B - Organic luminescent material composition, organic luminescent ink, luminescent film and device - Google Patents
Organic luminescent material composition, organic luminescent ink, luminescent film and device Download PDFInfo
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- CN115440903B CN115440903B CN202110617796.5A CN202110617796A CN115440903B CN 115440903 B CN115440903 B CN 115440903B CN 202110617796 A CN202110617796 A CN 202110617796A CN 115440903 B CN115440903 B CN 115440903B
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- organic luminescent
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- 239000000463 material Substances 0.000 title claims abstract description 210
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 230000003111 delayed effect Effects 0.000 claims abstract description 37
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 238000001748 luminescence spectrum Methods 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 59
- 230000005281 excited state Effects 0.000 claims description 17
- 238000001228 spectrum Methods 0.000 claims description 14
- NUEUMFZLNOCRCQ-UHFFFAOYSA-N 1-propan-2-yl-4-(4-propan-2-ylphenyl)benzene Chemical group C1=CC(C(C)C)=CC=C1C1=CC=C(C(C)C)C=C1 NUEUMFZLNOCRCQ-UHFFFAOYSA-N 0.000 claims description 13
- NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical class 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 3
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 claims description 2
- LHNUPUGVRFQTLK-UHFFFAOYSA-N 1-propan-2-yl-3-(4-propan-2-ylphenyl)benzene Chemical group C1=CC(C(C)C)=CC=C1C1=CC=CC(C(C)C)=C1 LHNUPUGVRFQTLK-UHFFFAOYSA-N 0.000 claims description 2
- UADWUILHKRXHMM-UHFFFAOYSA-N 2-ethylhexyl benzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1 UADWUILHKRXHMM-UHFFFAOYSA-N 0.000 claims description 2
- DUAYDERMVQWIJD-UHFFFAOYSA-N 2-n,2-n,6-trimethyl-1,3,5-triazine-2,4-diamine Chemical compound CN(C)C1=NC(C)=NC(N)=N1 DUAYDERMVQWIJD-UHFFFAOYSA-N 0.000 claims description 2
- KYZHGEFMXZOSJN-UHFFFAOYSA-N benzoic acid isobutyl ester Natural products CC(C)COC(=O)C1=CC=CC=C1 KYZHGEFMXZOSJN-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims description 2
- UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 claims description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 claims description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- CDKDZKXSXLNROY-UHFFFAOYSA-N octylbenzene Chemical compound CCCCCCCCC1=CC=CC=C1 CDKDZKXSXLNROY-UHFFFAOYSA-N 0.000 claims description 2
- 238000000103 photoluminescence spectrum Methods 0.000 claims description 2
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 3
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 claims 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 claims 1
- ABZRXXLIXJOIOC-UHFFFAOYSA-N 5-methyl-1-phenylisoquinoline Chemical compound N1=CC=C2C(C)=CC=CC2=C1C1=CC=CC=C1 ABZRXXLIXJOIOC-UHFFFAOYSA-N 0.000 claims 1
- ZPHQFGUXWQWWAA-UHFFFAOYSA-N 9-(2-phenylphenyl)carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 ZPHQFGUXWQWWAA-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- DBNYWRKRZTXMCU-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 DBNYWRKRZTXMCU-UHFFFAOYSA-N 0.000 claims 1
- WHLNMCZCHNKKDQ-UHFFFAOYSA-N iridium;3-methylphenanthro[9,10-b]pyrazine Chemical compound [Ir].C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1.C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1 WHLNMCZCHNKKDQ-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- 238000007641 inkjet printing Methods 0.000 abstract description 13
- 230000008569 process Effects 0.000 abstract description 8
- 239000010410 layer Substances 0.000 description 82
- 239000000976 ink Substances 0.000 description 63
- 239000010408 film Substances 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 28
- 239000000758 substrate Substances 0.000 description 26
- 238000012546 transfer Methods 0.000 description 14
- 238000007725 thermal activation Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000010409 thin film Substances 0.000 description 11
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 8
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 7
- 239000002131 composite material Substances 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 5
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 5
- 229920000144 PEDOT:PSS Polymers 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- -1 di (1-phenyl-5-methylisoquinoline) (acetylacetone) iridium Chemical compound 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 2
- GJHHESUUYZNNGV-UHFFFAOYSA-N 2-(2,4-difluorobenzene-6-id-1-yl)pyridine;iridium(3+) Chemical compound [Ir+3].FC1=CC(F)=C[C-]=C1C1=CC=CC=N1.FC1=CC(F)=C[C-]=C1C1=CC=CC=N1.FC1=CC(F)=C[C-]=C1C1=CC=CC=N1 GJHHESUUYZNNGV-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZNSXNNUEMWLJEV-UHFFFAOYSA-N 4-butan-2-yl-n,n-diphenylaniline Chemical compound C1=CC(C(C)CC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ZNSXNNUEMWLJEV-UHFFFAOYSA-N 0.000 description 1
- YFHRIUJZXWFFHN-UHFFFAOYSA-N 9-(1-carbazol-9-yl-5-phenylcyclohexa-2,4-dien-1-yl)carbazole Chemical group C=1C=CC(N2C3=CC=CC=C3C3=CC=CC=C32)(N2C3=CC=CC=C3C3=CC=CC=C32)CC=1C1=CC=CC=C1 YFHRIUJZXWFFHN-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- MULIMVVSVMFDQR-UHFFFAOYSA-N [Ir].C(C)(=O)CC(C)=O.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 Chemical compound [Ir].C(C)(=O)CC(C)=O.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 MULIMVVSVMFDQR-UHFFFAOYSA-N 0.000 description 1
- SROUTDZAHLYYOQ-UHFFFAOYSA-N [Ir]C=O.C1=CC=NC=C1 Chemical compound [Ir]C=O.C1=CC=NC=C1 SROUTDZAHLYYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001296 phosphorescence spectrum Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The embodiment of the application discloses an organic luminescent material composition and organic luminescent ink containing the same. The organic luminescent material composition includes a host material, a phosphorescent material, and a thermally activated delayed fluorescence material. The organic luminescent material composition has higher color purity and high-efficiency fluorescence emission. The organic luminescent ink prepared from the organic luminescent material composition can meet the requirements of an ink-jet printing process on boiling point, viscosity and surface tension, and simultaneously can improve the performances of current efficiency, color purity and the like of an organic electroluminescent device prepared by using the organic luminescent ink, narrow the luminescence spectrum of the organic electroluminescent device and facilitate the realization of high-color-gamut display. The application also discloses an organic light-emitting film prepared by using the organic light-emitting ink and an organic electroluminescent device comprising the organic light-emitting film.
Description
Technical Field
The application relates to the technical field of organic luminescent materials, in particular to an organic luminescent material composition, organic luminescent ink containing the organic luminescent material composition, an organic luminescent film prepared from the organic luminescent ink and an organic electroluminescent device using the organic luminescent film.
Background
An OLED (Organic Light-Emitting Diode), also known as an Organic laser display, an Organic Light-Emitting semiconductor (Organic Electroluminescence Display, OLED), is a device that utilizes a multilayer Organic thin film structure to produce electroluminescence. The luminous principle of the OLED is that an organic luminous film-luminous layer with the thickness of tens of nanometers is manufactured on ITO glass, a metal electrode is arranged above the luminous layer, voltage is applied to the electrode, and the luminous layer generates light radiation; electrons and holes are respectively injected from the cathode and anode, the injected electrons and holes are transmitted in the organic layer and are combined in the light-emitting layer, the molecules of the light-emitting layer are excited to generate singlet excitons, and the singlet excitons radiate to attenuate light emission, so that each pixel point is formed. The OLED does not need an extra light source, is lighter and thinner than an LCD, has high brightness, low power consumption, quick response, high definition, good flexibility and high luminous efficiency, and is favored by wide consumers.
The existing manufacturing process of the organic light-emitting film mainly comprises two processes of evaporation plating and ink-jet printing. The evaporation must be performed in a vacuum chamber, which is costly and complex. The ink-jet printing is like ink-jet printing on paper, adopts soluble OLED materials, is configured into printable functional layer ink, and is printed into pixel pits drop by drop to realize patterned display. Compared with the evaporation technology, the ink-jet printing does not need high vacuum, has low equipment cost, simple process and low material consumption.
However, the organic light-emitting material used in the existing organic light-emitting layer is not high enough in light-emitting efficiency, and the light-emitting color purity of the electroluminescent device is not high due to the wide half-width of the light-emitting spectrum, which is unfavorable for realizing the display effect of high color gamut.
Disclosure of Invention
The embodiment of the application provides an organic luminescent material composition which is used for improving the luminous efficiency of an organic luminescent film.
Embodiments of the present application provide an organic light emitting material composition including a host material, a phosphorescent material, and a thermally activated delayed fluorescence material.
Correspondingly, the embodiment of the application also provides organic luminescent ink which comprises a solvent and the organic luminescent material composition.
Correspondingly, the embodiment of the application also provides an organic luminescent film, which is prepared from the organic luminescent material composition or the organic luminescent ink.
In addition, the embodiment of the application also provides an organic electroluminescent device, which comprises an anode, a luminescent layer and a cathode which are sequentially stacked, wherein the luminescent layer is prepared from the organic luminescent material composition or the organic luminescent ink.
The organic luminescent material composition of the embodiment of the application comprises a main body material, a phosphorescent material and a thermally activated delayed fluorescence material, and has high-efficiency fluorescence emission. The organic luminescent ink prepared from the organic luminescent material composition can meet the requirements of an ink-jet printing process on boiling point, viscosity and surface tension, and can improve the current efficiency and other performances of an organic electroluminescent device prepared by using the organic luminescent ink.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present application, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a schematic view of the luminescence mechanism of an organic luminescent material composition according to an embodiment of the present application;
Fig. 2 is a schematic diagram of an organic electroluminescent device according to an embodiment of the present application;
FIG. 3 is a schematic diagram of another organic electroluminescent device according to an embodiment of the present application;
Fig. 4 is an electroluminescence spectrum of the organic electroluminescent device of example 9 (solid line) and comparative example 6 (broken line).
Detailed Description
The following description of the embodiments of the present application will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to fall within the scope of the application.
Embodiments of the present application provide an organic light emitting material composition. The following will describe in detail. The following description of the embodiments is not intended to limit the preferred embodiments. In addition, in the description of the present application, the term "comprising" means "including but not limited to". The terms first, second, third and the like are used merely as labels, and do not impose numerical requirements or on the order of construction. Various embodiments of the application may exist in a range of forms; it should be understood that the description in a range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the application; it is therefore to be understood that the range description has specifically disclosed all possible sub-ranges as well as single numerical values within the ranges. For example, it should be considered that a description of a range from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the ranges, such as 1, 2, 3,4, 5, and 6, wherever applicable. In addition, whenever a numerical range is referred to herein, it is meant to include any reference number (fractional or integer) within the indicated range.
The preferred embodiment of the application provides an organic luminescent material composition which comprises a main body material, a phosphorescent material and a heat activation delay fluorescent material.
The organic luminescent material composition comprises 65-96.5wt% of host material, 3-30wt% of phosphorescent material and 0.5-5wt% of heat activation delay fluorescent material. Wherein, the content range of the thermal activation delay fluorescent material is determined by the energy transfer efficiency and the charge trap caused by the concentration, and when the content is lower than 0.5wt%, the energy transfer from the phosphorescent material to the thermal activation delay fluorescent material is incomplete, the spectrum is not completely narrowed, and the energy transfer efficiency is lower; at levels above 5wt%, excitons may be directly trapped by the thermally activated delayed fluorescent material, creating a large number of charge traps, leading to energy loss and a decrease in luminous efficiency.
Referring to FIG. 1, in the organic light emitting material composition, triplet energy generated on a host material can be transferred to a phosphorescent material by means of Dexter energy transfer (Dexter ET, dexter excitation transfer), or can be transferred back to a singlet state by reverse intersystem crossing (RISC), and then passed throughThe energy transfer mode is transferred to the singlet state of the phosphorescent material, so that the exciton utilization rate of 100% can be realized. In addition, the singlet state (S 1) and the triplet state (T 1) of the phosphorescent material have a near 0 energy level difference due to the heavy atom coupling effect, thereby having high intersystem crossing (ISC) efficiency, so that the singlet energy of the phosphorescent material can be completely transferred to the triplet state. Triplet excitons of phosphorescent materials may passEnergy transfer (F6 rster ET) to the singlet state of the thermally activated delayed fluorescent material.
In one embodiment, the host material satisfies the following formula:
E S1,H-ET1,H is less than or equal to 0.3eV (formula I),
Wherein E S1,H is the singlet excited state energy level of the host material, and E T1,H is the triplet excited state energy level of the host material.
The difference between the singlet excited state energy level and the triplet excited state energy level of the host material is less than 0.3eV (formula I) to enable the host material to have the characteristic of thermal activation delayed fluorescence, so that the triplet energy of the host material can be transmitted back to the singlet state through reverse intersystem crossing (RISC) and can be further transmitted throughEnergy transferET) process is transferred to phosphorescent material. This can be achieved even when the triplet excited state energy level of the host material is lower than that of the phosphorescent material, contributing to a reduction in efficiency loss caused by triplet exciton quenching, thereby improving light emission efficiency.
In one embodiment, the phosphorescent material and the thermally activated delayed fluorescence material satisfy the following formula:
E T1,PH-ES1,TADF is less than or equal to 0.2eV (formula II),
Wherein E T1,PH is the triplet excited state energy level of the phosphorescent material, and E S1,TADF is the singlet excited state energy level of the thermally activated delayed fluorescent material.
The difference in energy level between the phosphorescent material and the thermally activated delayed fluorescent material is less than 0.2eV (formula II), which can enable the organic luminescent material composition to realize effective energy transfer from the phosphorescent material to the thermally activated delayed fluorescent material, thereby improving energy transfer efficiency.
The singlet and triplet excited states in the above formula I, II are obtained by low-temperature fluorescence and phosphorescence spectrum tests, and are calculated as the value of the initial peak position of the emission spectrum, e=1240/λ.
To further achieve narrow-spectrum luminescence, the luminescence spectrum half-width FWHM TADF of the thermally activated delayed fluorescent material satisfies the following formula:
FWHM TADF.ltoreq.45 nm (formula III).
The formula III defines the half-peak width of the thermally activated delayed fluorescent material such that the thermally activated delayed fluorescent material has the property of narrowing the spectrum, which is beneficial for achieving narrow spectrum fluorescent emission.
In order to make the organic electroluminescent device prepared from the organic luminescent material composition have better luminous efficiency, the half-width FWHM PH of the photoluminescence spectrum of the phosphorescent material and the half-width FWHM TADF of the luminescence spectrum of the thermally activated delayed fluorescent material satisfy the following formulas:
FWHMPH-FWHMTADF≥15nm
(formula IV).
The host material is an acceptor-donating host material having an electron donating group and an electron withdrawing group. The electron donating group can be selected from one or more of aniline, carbazole, thiophene and furan. The electron withdrawing group can be selected from one or more of pyridine, triazine, quinoline and oxazole.
In at least one embodiment, the host material is an n-type host material having electron withdrawing groups. The n-type host material having an electron withdrawing group may be selected from, but is not limited to, one of materials having the following structural formula:
In yet another embodiment, the host material may also be a p-type host material having an electron donating group. The p-type host material having an electron donating group may be selected from, but not limited to, one or more of CBP (Chinese name: 4,4 '-bis (9-carbazole) biphenyl, CAS number 58328-31-7), mCBP (Chinese name: 3, 3-bis (N-carbazolyl) -1, 1-biphenyl, CAS number: 342638-54-4), TCTA (Chinese name: 4,4',4 "-tris (carbazol-9-yl) triphenylamine, CAS number: 139092-78-7), and materials having the following structural formula:
It is understood that in yet another embodiment, the host material in the organic light emitting material composition may include the n-type host material and the p-type host material.
The phosphorescent material may be, but is not limited to, a metal complex that emits light using triplet excitons. The phosphorescent material includes, but is not limited to, one or more of a blue phosphorescent material, a green phosphorescent material, and a red phosphorescent material. The blue phosphorescent material is selected from one or two of FIrpic and Fir 6. The green phosphorescent material is selected from one or more of Ir (ppy) 3, ir (ppy) 2 (acac) and Ir (mppy) 3. The red phosphorescent material is selected from one or more of Ir (piq) 2 (acac), ir (m-piq) 2 (acac) and Ir (MDQ) 2 (acac), but not limited to.
Wherein the Chinese name of FIrpic is bis (4, 6-difluorophenylpyridine-N, C2) pyridine formyliridium, CAS number is 376367-93-0, and the structural formula is as follows:
the Chinese name of Fir6 is iridium (III) bis (2, 4-difluorophenylpyrido) tetra (1-pyrazolyl) borate, the CAS number is 664374-03-2, and the structural formula is as follows:
The Chinese name of Ir (ppy) 3 is tris (2-phenylpyridine) iridium (III), the CAS number is 94928-86-6, and the structural formula is as follows:
The Chinese name of Ir (ppy) 2 (acac) is iridium acetylacetonate di (2-phenylpyridine), the CAS number is 337526-85-9, and the structural formula is as follows:
the Chinese name of Ir (mppy) 3 is tris [2- (p-tolyl) pyridine ] iridium (III), the CAS number is 800394-58-5, and the chemical structural formula is as follows:
the Chinese name of Ir (piq) 2 (acac) is di (1-phenylisoquinoline) (acetylacetone) iridium, the CAS number is 435294-03-4, and the structural formula is as follows:
the Chinese name of Ir (m-piq) 2 (acac) is di (1-phenyl-5-methylisoquinoline) (acetylacetone) iridium, and the structural formula is as follows:
the Chinese name of Ir (MDQ) 2 (acac) is (acetylacetone) bis (2-methyldibenzo [ F, H ] quinoxaline) iridium, the CAS number is 536755-34-7, and the structural formula is as follows:
The thermally activated delayed fluorescence material may be selected from, but is not limited to, one or more of DABNA-1, DABNA-2, t-DABA, TBN-TPA, B2, BBCz-DB, v-DABA, OAB-ABP-1, 3F-BN, m-Cz-BNCz, AZA-BN, BBCz-G, and BBCz-R.
Wherein, the structural formula of DABNA-1 is as follows:
The structural formula of DABNA-2 is as follows:
the structural formula of t-DABNA is as follows:
The structural formula of the TBN-TPA is as follows:
The structural formula of the B2 is as follows:
the BBCz-DB has the following structural formula:
the structural formula of v-DABNA is as follows:
The structural formula of the OAB-ABP-1 is as follows:
the structural formula of the 3F-BN is as follows:
The structural formula of the m-Cz-BNCz is as follows:
The structural formula of the AZA-BN is as follows:
The structural formula of BBCz-G is as follows:
The structural formula of BBCz-R is as follows:
The embodiment of the application also provides organic luminescent ink, which comprises the organic luminescent material composition and a solvent. In the organic luminescent ink, the content of the organic luminescent material composition ranges from 0.5 to 7.5 weight percent, and the content of the solvent ranges from 92.5 to 99.5 weight percent.
The solvent may contain only one kind of solvent, or may contain two or more kinds of solvents at the same time. Preferably, the solvent contains two or more solvents, in other words, the solvent is a mixed solvent formed by mixing two or more solvents. Each of the two or more solvents has a different boiling point, and the difference in boiling point between the solvents is 50 ℃ or more. In this way, an inward flow of Marangoni (Marangoni) may be formed, which may suppress the "coffee ring" effect during the drying film forming process, thereby helping to obtain a uniform film layer.
In at least one embodiment, the solvent consists of solvent a and solvent B. The boiling point difference value of the solvent A and the solvent B is more than or equal to 50 ℃. The solvent A is a benzoate solvent, and the benzoate solvent is one or more selected from methyl benzoate, ethyl p-methylbenzoate, isobutyl benzoate and ethylhexyl benzoate. The solvent B is an alkyl substituted aromatic benzene solvent, and the alkyl substituted aromatic benzene solvent is selected from one or more of cyclohexylbenzene, 1-hexylbenzene, 1-heptylbenzene, 1-octylbenzene, 1-decylbenzene, 4' -diethylbiphenyl, 3,4' -diisopropylbiphenyl and 4,4' -diisopropylbiphenyl.
It will be appreciated that the organic luminescent ink may also include other additives that may be applied to the organic luminescent ink, such as polymerization inhibitors, stabilizers, thickeners, gelling agents, flame retardants, antioxidants, anti-reducing agents, oxidizing agents, reducing agents, surface modifying agents, emulsifiers, defoamers, dispersants, surfactants, and the like.
The viscosity range of the organic luminous ink at room temperature of 25 ℃ is 2-10cp, and the surface tension range is 28-40mN/m. Thus, the organic luminescent ink can be ensured to have good printability and wettability on the substrate.
The embodiment of the application also provides a preparation method of the organic luminescent ink, which comprises the following steps:
step S01: adding a main body material, a phosphorescent material and a thermal activation delay fluorescent material into a certain amount of solvent according to a certain proportion, and uniformly mixing to obtain a mixture;
step S02: heating and stirring the mixture at 50-100deg.C for 0.5-24 hr until the main material, phosphorescent material and thermally activated delayed fluorescence material are completely dissolved;
step S03: filtering to remove impurities to obtain the organic luminous printing ink.
The mixing method in the step S01 may be a known mixing method such as shaking, ultrasonic wave, and shaking.
In at least one embodiment, a filter head of 0.2 μm is used for the filtering in the step S03. It will be appreciated that in other embodiments, other conventionally used filtration devices and methods of filtration may be employed for filtration.
The embodiment of the application also provides an organic light-emitting film prepared from the organic light-emitting ink.
The embodiment of the application also provides a preparation method of the organic light-emitting film, which comprises the following steps:
step S11: providing a substrate;
step S12: depositing the organic luminescent ink on the substrate by inkjet printing;
Step S13: vacuum drying, removing residual solvent, and forming an organic light-emitting film layer;
step S14: and (5) baking at high temperature to obtain the organic light-emitting film.
In the step S14, the high-temperature baking temperature is 80-150 ℃ and the baking time is 15-20min.
Referring to fig. 2, an embodiment of the present application further provides an organic electroluminescent device 100, which may be a top-emitting organic electroluminescent device or a bottom-emitting organic electroluminescent device. The organic electroluminescent device 100 comprises a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, a cathode 7, an encapsulation layer 8 and a cover plate 9 which are sequentially stacked. Wherein the light emitting layer 5 is a layer formed of the organic light emitting thin film.
It will be appreciated that the substrate 1 is a substrate for application to an organic electroluminescent device as known in the art. In at least one embodiment, the substrate 1 is a glass substrate.
It will be appreciated that the anode 2 is an anode as known in the art for use in an organic electroluminescent device. In at least one embodiment, the anode 2 is ITO (tin-indium oxide) or IZO (zinc-indium oxide).
It is understood that the hole injection layer 3 is a hole injection layer applied to an organic electroluminescent device as known in the art. In at least one embodiment, the hole injection layer 3 is PEDOT: PSS (poly 3, 4-ethylenedioxythiophene: polystyrene sulfonate), and has the following structural formula:
It is understood that the hole transport layer 4 is a hole transport layer known in the art to be applied to an organic electroluminescent device. In at least one embodiment, the hole transport layer 4 is a PVK (poly (9-vinylcarbazole)) film or TFB (poly [ (9, 9-dioctylfluorene-2, 7-diyl) -co- (4, 4' - (N- (4-sec-butylphenyl) diphenylamine) ]) having the following structural formula:
It will be appreciated that the electron transport layer 6 is an electron transport layer as known in the art for use in organic electroluminescent devices. In at least one embodiment, the electron transport layer 6 is TmPyPB (3, 3'- [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1 '-terphenyl ] -3, 3' -diyl ] bipyridine).
It will be appreciated that the cathode 7 is a cathode as known in the art for use in an organic electroluminescent device. In at least one embodiment, the cathode 7 is a LiF/Al composite electrode or a Yb/Ag composite electrode.
The encapsulation layer 8 is an encapsulation material known in the art for application to organic electroluminescent devices.
The cover plate 9 is a transparent plate material such as glass, plastic and the like which is known in the art and is applied to an organic electroluminescent device.
Referring to fig. 3, in yet another embodiment, the organic electroluminescent device 100 may further include a reflective layer 10 between the substrate 1 and the anode 2 and an optical coupling layer 20 between the cathode 7 and the encapsulation layer 8.
It is understood that the optical coupling layer 20 is an optical coupling layer applied to an organic electroluminescent device as known in the art. In at least one embodiment, the optical coupling layer 20 is NPB (N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine).
It is understood that the reflective layer 10 is a reflective layer applied to an organic electroluminescent device as known in the art. In at least one embodiment, the reflective layer 10 is Ag.
The embodiment of the application also provides a preparation method of the top-emission organic electroluminescent device, which comprises the following steps:
step S1: providing a substrate 1;
step S2: a reflection layer 10, an anode 2, a hole injection layer 3, and a hole transport layer 4 are sequentially formed on the surface of the substrate 1;
Step S3: forming a light-emitting layer 5 on the surface of the hole transport layer 4 by a solution method;
Step S4: an electron transport layer 6, a cathode 7 and an optical coupling layer 20 are sequentially formed on the surface of the light emitting layer 5;
step S5: providing an encapsulation layer 8 on the surface of the optical coupling layer 20;
step S6: a cover plate 9 is provided on the surface of the encapsulation layer 8 remote from the optical coupling layer 20.
It is understood that the methods for forming the reflective layer 10, the anode 2, the hole injection layer 3, the hole transport layer 4, the electron transport layer 6, the cathode 7, and the optical coupling layer 20 are evaporation methods, sputtering methods, solution methods, and the like, which are known in the art.
It is understood that when the organic electroluminescent device 100 does not include the reflective layer 10 and the optical coupling layer 20, the step of forming the reflective layer 10 and the optical coupling layer 20 may be omitted.
The embodiment of the present application also provides an electroluminescent display device (not shown) comprising a substrate, a driving TFT unit on the substrate, and the organic electroluminescent device 100 on the driving TFT unit.
The present application will now be described in more detail by way of the following examples, which are intended to be illustrative of the application and not limiting thereof.
Example 1
In the organic luminescent ink of the embodiment, the main material is a compound with a structural formula Host-1, the phosphorescent material is Ir (mppy) 3, the thermal activation delay fluorescent material is m-Cz-BNCz, and the solvent is a mixed solvent of ethyl p-methylbenzoate and 4,4' -diisopropylbiphenyl. Wherein, E S1,H of Host-1 is 2.81eV and E T1,H is 2.66eV. E T1,PH of Ir (mppy) 3 was 2.50eV and FWHM PH was 70nm. E S1,TADF of m-Cz-BNCz was 2.50eV and FWHM TADF was 38nm.
In the organic luminescent ink of this embodiment, the mass percentage of the host material is 1.25wt%, the mass percentage of the phosphorescent material is 0.10wt%, the mass percentage of the thermally activated delayed fluorescent material is 0.05wt%, the mass percentage of the solvent ethyl p-methylbenzoate is 34.5wt%, and the mass percentage of the solvent 4,4' -diisopropylbiphenyl is 64.1wt%.
The preparation method of the organic luminescent ink of the embodiment comprises the following steps: adding the main material, the phosphorescent material and the thermal activation delay fluorescent material into a solvent, stirring for 12 hours at 80 ℃, and filtering by a 0.2 mu m filter head to obtain the organic luminous ink.
The organic luminescent ink of this example had a viscosity of 3.5cp at 25℃and a surface tension of 32mN/m.
Example 2
In the organic luminescent ink of the embodiment, the main material is a compound with structural formulas of Host-4 and p-Host-4, the phosphorescent material is Ir (mppy) 3, the thermal activation delay fluorescent material is m-Cz-BNCz, and the solvent is a mixed solvent of ethyl p-methylbenzoate and 4,4' -diisopropylbiphenyl. Wherein, E S1,H of Host-4 is 2.82eV and E T1,H is 2.64eV. E T1,PH of Ir (mppy) 3 was 2.50eV and FWHM PH was 70nm. E S1,TADF of m-Cz-BNCz was 2.50eV and FWHM TADF was 38nm.
In the organic luminescent ink of the embodiment, the mass percentage of the Host material Host-4 is 0.9wt%, the mass percentage of the Host material p-Host-4 is 0.6wt%, the mass percentage of the phosphorescent material is 0.12wt%, the mass percentage of the thermally activated delayed fluorescent material is 0.06wt%, the mass percentage of the solvent ethyl p-methylbenzoate is 36.38wt%, and the mass percentage of the solvent 4,4' -diisopropylbiphenyl is 61.94wt%.
The preparation method of the organic luminescent ink of the embodiment comprises the following steps: adding the main material, the phosphorescent material and the thermal activation delay fluorescent material into a solvent, stirring for 12 hours at 80 ℃, and filtering by a 0.2 mu m filter head to obtain the organic luminous ink.
The organic luminescent ink of this example had a viscosity of 3.6cp at 25℃and a surface tension of 33mN/m.
Example 3
In the organic luminescent ink of the embodiment, the main material is a compound with a structural formula of Host-3, the phosphorescent material is Ir (m-piq) 2 (acac), the thermal activation delay fluorescent material is BBCz-R, and the solvent is a mixed solvent of ethyl p-methylbenzoate and 4,4' -diisopropylbiphenyl. Wherein, E S1,H of Host-3 is 2.82eV and E T1,H is 2.68eV. Ir (m-piq) 2 (acac) has an E T1,PH of 2.08eV and a FWHM PH of 72nm. BBCz-R has an E S1,TADF of 2.10eV and a FWHM TADF of 27nm.
In the organic luminescent ink of this embodiment, the mass percentage of the host material is 1.35wt%, the mass percentage of the phosphorescent material is 0.07wt%, the mass percentage of the thermally activated delayed fluorescent material is 0.03wt%, the mass percentage of the solvent ethyl p-methylbenzoate is 34.5wt%, and the mass percentage of the solvent 4,4' -diisopropylbiphenyl is 64.05wt%.
The preparation method of the organic luminescent ink of the embodiment comprises the following steps: adding the main material, the phosphorescent material and the thermal activation delay fluorescent material into a solvent, stirring for 12 hours at 80 ℃, and filtering by a 0.2 mu m filter head to obtain the organic luminous ink.
The organic luminescent ink of this example had a viscosity of 3.6cp at 25℃and a surface tension of 32mN/m.
Example 4
In the organic luminescent ink of the embodiment, the main material is a compound with structural formulas of Host-7 and m-CBP, the phosphorescent material is FIrpic, the thermal activation delay fluorescent material is t-DABNA, and the solvent is a mixed solvent of ethyl p-methylbenzoate and 4,4' -diisopropylbiphenyl. Wherein Host-7 has an E S1,H of 3.18eV and E T1,H of 2.90eV. FIrpic has an E T1,PH of 2.72eV and a FWHM PH of 60nm. E S1,TADF of t-DABNA was 2.80eV and FWHM TADF was 27nm.
In the organic luminescent ink of the embodiment, the mass percentage of the Host material Host-7 is 0.36wt%, the mass percentage of the m-CBP is 0.84wt%, the mass percentage of the phosphorescent material is 0.12wt%, the mass percentage of the thermally activated delayed fluorescent material is 0.03wt%, the mass percentage of the solvent ethyl p-methylbenzoate is 39.5wt%, and the mass percentage of the solvent 4,4' -diisopropylbiphenyl is 59.15wt%.
The preparation method of the organic luminescent ink of the embodiment comprises the following steps: adding the main material, the phosphorescent material and the thermal activation delay fluorescent material into a solvent, stirring for 12 hours at 80 ℃, and filtering by a 0.2 mu m filter head to obtain the organic luminous ink.
The organic luminescent ink of this example had a viscosity of 3.6cp at 25℃and a surface tension of 33mN/m.
Example 5
The organic light emitting ink prepared in example 1 was deposited on a substrate by inkjet printing, then vacuum dried, and baked at 120 ℃ for 20min to obtain an organic light emitting thin film having a thickness of 62 nm.
The thickness uniformity of the organic light emitting thin film of this example was measured by a white light interferometer to be 70%.
Example 6
The organic light emitting ink prepared in example 2 was deposited on a substrate by inkjet printing, then vacuum dried, and baked at 120 ℃ for 20min to obtain an organic light emitting thin film having a thickness of 60 nm.
The film thickness uniformity of the organic light emitting thin film of this example was measured by a white light interferometer and found to be 72%.
Example 7
The organic light emitting ink prepared in example 3 was deposited on a substrate by inkjet printing, then vacuum dried, and baked at 120 ℃ for 20min to obtain an organic light emitting thin film having a thickness of 81 nm.
The uniformity of the film thickness of the organic light emitting thin film of this example was 73% by white light interferometer test.
Example 8
The organic light emitting ink prepared in example 4 was deposited on a substrate by inkjet printing, then vacuum dried, and baked at 120 ℃ for 20min to obtain an organic light emitting thin film having a thickness of 32 nm.
The organic light emitting thin film of this example was tested by a white light interferometer for film thickness uniformity of 75%.
Example 9
Organic electroluminescent device
The substrate 1 of the organic electroluminescent device of the present embodiment is a glass substrate. The anode 2 is ITO with a thickness of 50nm. The hole injection layer 3 was PEDOT: PSS, 35nm thick. The hole transport layer 4 was PVK and had a thickness of 20nm. The light-emitting layer 5 was an organic light-emitting film prepared in example 1, and the thickness was 60nm. The electron transport layer 6 was TmPyPB and had a thickness of 30nm. The cathode 7 is a LiF/Al composite electrode, wherein the thickness of the LiF film layer is 1nm, and the thickness of the Al film layer is 150nm. The cover plate 9 is a glass cover plate.
Example 10
This example was substantially identical to the preparation method of example 9, except that the light-emitting layer 5 was an organic light-emitting film prepared in example 2.
Comparative example 1
The composition of the organic light-emitting ink of this comparative example was substantially the same as that of the organic light-emitting ink of example 1 and the preparation method was the only difference that p-host-4 was used as the host material in the organic light-emitting ink of this comparative example compared to example 1, wherein E S1,H of p-host-4 was 3.08eV and E T1,H was 2.67eV.
In the organic luminescent ink of the comparative example, the mass percentage of the main material p-host-4 is 1.25wt%, the mass percentage of the phosphorescent material is 0.10wt%, the mass percentage of the thermally activated delayed fluorescent material is 0.05wt%, the mass percentage of the solvent ethyl p-methylbenzoate is 34.5wt%, and the mass percentage of the solvent 4,4' -diisopropylbiphenyl is 64.1wt%.
Comparative example 2
The composition of the organic light-emitting ink of this comparative example was substantially the same as that of the organic light-emitting ink of example 1 and the preparation method was the only difference that Ir (Fppy) 3 was used as a phosphorescent material in the organic light-emitting ink of this comparative example compared with example 1, and the triplet excited state level E T1,PH was 2.63eV.
In the organic luminescent ink of the comparative example, the mass percentage of the Host material Host-3 is 1.25wt%, the mass percentage of the phosphorescent material is 0.10wt%, the mass percentage of the thermally activated delayed fluorescent material is 0.05wt%, the mass percentage of the solvent ethyl p-methylbenzoate is 34.5wt%, and the mass percentage of the solvent 4,4' -diisopropylbiphenyl is 64.1wt%.
Comparative example 3
The composition of the organic luminescent ink of this comparative example was substantially the same as that of the organic luminescent ink of example 1 and the preparation method, except that the organic luminescent ink of comparative example 3 contained no heat-activated delayed fluorescence material m-Cz-BNCz as compared with example 1.
In the organic luminescent ink of the comparative example, the mass percentage of the Host material Host-3 is 1.25wt%, the mass percentage of the phosphorescent material is 0.15wt%, the mass percentage of the solvent ethyl p-methylbenzoate is 34.5wt%, and the mass percentage of the solvent 4,4' -diisopropylbiphenyl is 64.1wt%.
The organic light emitting inks of comparative examples 1 to 3 were deposited on a substrate by inkjet printing, respectively, and then vacuum dried, and baked at 120℃for 20 minutes, to obtain an organic light emitting film having a thickness of 61 nm. The uniformity of film thickness of the organic light emitting thin films of comparative examples 1 to 3 was 73%, 72%, 71%, respectively, as measured by white light interferometer.
Comparative example 4
The substrate of the organic electroluminescent device of this embodiment is a glass substrate. The anode is ITO with the thickness of 50nm. The hole injection layer is PEDOT: PSS with the thickness of 35nm. The hole transport layer was PVK and had a thickness of 20nm. The light-emitting layer was an organic light-emitting film prepared in comparative example 1, which had a thickness of 60nm. The electron transport layer was TmPyPB and had a thickness of 30nm. The cathode is a LiF/Al composite electrode, wherein the thickness of the LiF film layer is 1nm, and the thickness of the Al film layer is 150nm. The cover plate 9 is a glass cover plate.
Comparative example 5
The substrate of the organic electroluminescent device of this embodiment is a glass substrate. The anode is ITO with the thickness of 50nm. The hole injection layer is PEDOT: PSS with the thickness of 35nm. The hole transport layer was PVK and had a thickness of 20nm. The light-emitting layer was an organic light-emitting film prepared in comparative example 2, which had a thickness of 60nm. The electron transport layer was TmPyPB and had a thickness of 30nm. The cathode is a LiF/Al composite electrode, wherein the thickness of the LiF film layer is 1nm, and the thickness of the Al film layer is 150nm. The cover plate 9 is a glass cover plate.
Comparative example 6
The substrate of the organic electroluminescent device of this embodiment is a glass substrate. The anode is ITO with the thickness of 50nm. The hole injection layer is PEDOT: PSS with the thickness of 35nm. The hole transport layer was PVK and had a thickness of 20nm. The light-emitting layer was an organic light-emitting film prepared in comparative example 3, which had a thickness of 60nm. The electron transport layer was TmPyPB and had a thickness of 30nm. The cathode is a LiF/Al composite electrode, wherein the thickness of the LiF film layer is 1nm, and the thickness of the Al film layer is 150nm. The cover plate 9 is a glass cover plate.
The electroluminescent spectra of the organic electroluminescent devices of example 9 and comparative example 6 were examined, and the electroluminescent spectrum graph is shown in fig. 4.
As can be seen from fig. 4, the organic electroluminescent device of example 9 has a narrower half-width of emission spectrum compared to the organic electroluminescent device of comparative example 6 prepared using the organic luminescent ink without the heat-activated delayed fluorescent material. It is explained that by doping the thermally activated delayed fluorescent material, there is sufficient energy transfer between the phosphorescent material and the narrow spectrum thermally activated delayed fluorescent material to achieve narrow spectrum emission.
Evaluation of the Performance of the organic electroluminescent devices of examples 9 to 10 and comparative examples 4 to 6
The evaluation method comprises the following steps: the current of the organic electroluminescent device at different voltages was measured using keithley2400 digital nanovoltmeter, and then divided by the light emitting area to obtain the current density. The luminance and radiant energy density of the organic electroluminescent device at different voltages were tested using Photo RESEARCH PR 655. And obtaining the current efficiency of the organic electroluminescent device according to the current density and the brightness of the organic electroluminescent device under different voltages.
The performance parameters of the organic electroluminescent devices of examples 9 to 10 and comparative examples 4 to 6 are shown in Table I.
Table one:
As can be seen from table one, the organic electroluminescent devices of examples 9 to 10 using Host-3 having the thermally activated delayed fluorescence property have significantly higher current efficiency and smaller decay of current efficiency at 1000nit than the maximum current efficiency, compared to comparative example 4 using Host material p-Host-4 having a larger singlet-triplet excited state energy level difference, which means that the Host material having the thermally activated delayed fluorescence property having a smaller singlet-triplet excited state energy level difference contributes to reduction of triplet exciton quenching through a rapid energy transfer process, thereby improving efficiency and reducing efficiency roll-off. Examples 9-10 use a dual host material to allow for more balanced carrier transport of the device, thus further improving device efficiency.
Compared with comparative example 5, the phosphorescent material Ir (Fppy) 3 with a higher triplet excited state energy level, the triplet excited state energy level E T1,PH is 2.63eV, and the energy transfer between the phosphorescent material and the thermally activated fluorescent material is incomplete, so that the efficiency of the electroluminescent device is lower, and meanwhile, the half-width of the electroluminescent device is not fully narrowed and the color coordinates are poorer as seen from light color.
Whereas comparative example 6 prepared an organic electroluminescent device using an organic luminescent ink without a heat-activated delayed fluorescent material, the half-width thereof was significantly wider than that of the organic electroluminescent devices of examples 9 to 10, whereas the half-width of an organic electroluminescent device using a narrow spectrum heat-activated delayed fluorescent material was narrowed, and CIE coordinates were reached (0.280,0.671) and (0.278,0.678), respectively. Therefore, the current efficiency, the color purity and other performances of the organic electroluminescent device using the organic luminescent ink doped with the narrow-spectrum heat-activated delayed fluorescent material are obviously improved.
The organic luminescent ink comprises a main body material, a phosphorescent material, a narrow-spectrum fluorescence doped luminescent material and a solvent. The organic luminescent ink can meet the requirements of an ink-jet printing process on boiling point, viscosity and surface tension, and meanwhile, the main material, the phosphorescent material and the narrow-spectrum fluorescence doped luminescent material can realize effective energy transfer, so that the performances of current efficiency, color purity and the like of an organic electroluminescent device prepared by using the organic luminescent ink can be improved, the luminescence spectrum of the organic electroluminescent device is narrowed, and high-color-gamut display is facilitated.
The organic luminescent material composition and the organic luminescent ink provided by the embodiment of the application are described in detail, and specific examples are applied to illustrate the principle and the implementation of the application, and the description of the above examples is only used for helping to understand the method and the core idea of the application; meanwhile, as those skilled in the art will have variations in the specific embodiments and application scope in light of the ideas of the present application, the present description should not be construed as limiting the present application.
Claims (15)
1. An organic luminescent material composition, characterized in that: the organic luminescent material composition comprises a host material, a phosphorescent material and a thermally activated delayed fluorescence material, wherein,
The host material is selected from materials shown in the following structural formula:
The phosphorescent material is selected from one or more of bis (4, 6-difluorophenylpyridine-N, C2) pyridine formylairidium, bis (2, 4-difluorophenylpyrido) iridium (III) tetra (1-pyrazolyl) borate, tris (2-phenylpyridine) iridium (III), bis (2-phenylpyridine) iridium acetylacetonate, tris [2- (p-tolyl) pyridine ] iridium (III), bis (1-phenylisoquinoline) (acetylacetonate) iridium, bis (1-phenyl-5-methylisoquinoline) (acetylacetonate) iridium and bis (2-methyldibenzo [ F, H ] quinoxaline) iridium (acetylacetonate);
The thermally activated delayed fluorescence material is selected from one or more of the following materials:
The organic luminescent material composition comprises 65-96.5wt% of host material, 3-30wt% of phosphorescent material and 0.5-5wt% of heat activation delay fluorescent material.
2. The organic luminescent material composition according to claim 1, wherein: the host material satisfies the following formula:
E S1,H-ET1,H is less than or equal to 0.3eV (formula I),
Wherein E S1,H is the singlet excited state energy level of the host material, and E T1,H is the triplet excited state energy level of the host material.
3. The organic luminescent material composition according to claim 1, wherein: the phosphorescent material and the thermally activated delayed fluorescence material satisfy the following formula:
E T1,PH-ES1,TADF is less than or equal to 0.2eV (formula II),
Wherein E T1,PH is the triplet excited state energy level of the phosphorescent material, and E S1,TADF is the singlet excited state energy level of the thermally activated delayed fluorescent material.
4. The organic luminescent material composition according to claim 1, wherein: the light-emitting spectrum half-width FWHM TADF of the heat-activated delayed fluorescent material meets the following formula:
FWHM TADF.ltoreq.45 nm (formula III).
5. The organic luminescent material composition according to claim 1, wherein: the full width at half maximum FWHM PH of the photoluminescence spectrum of the phosphorescent material and the full width at half maximum FWHM TADF of the luminescence spectrum of the thermally activated delayed fluorescent material satisfy the following formula:
FWHM PH-FWHMTADF is not less than 15nm (formula IV).
6. The organic luminescent material composition according to claim 1, wherein: the host material also comprises one or more of 4,4 '-bis (9-carbazole) biphenyl, 3-bis (N-carbazolyl) -1, 1-biphenyl, 4' -tris (carbazole-9-yl) triphenylamine and p-type host material with the following structural formula:
7. An organic luminescent ink comprising a solvent, characterized in that: the organic luminescent ink further comprises the organic luminescent material composition according to any one of claims 1-6.
8. The organic luminescent ink according to claim 7, wherein: in the organic luminescent ink, the content of the organic luminescent material composition ranges from 0.5 to 7.5 weight percent, and the content of the solvent ranges from 92.5 to 99.5 weight percent.
9. The organic luminescent ink according to claim 8, wherein: the solvent comprises two or more solvents, each of the two or more solvents has a different boiling point.
10. The organic luminescent ink according to claim 9, wherein: the difference of boiling points between the solvents in the two or more solvents is greater than or equal to 50 ℃.
11. The organic luminescent ink according to claim 7 or 10, wherein: the solvent comprises at least one of benzoate solvents and at least one of alkyl-substituted aromatic benzene solvents.
12. The organic luminescent ink according to claim 11, wherein: the benzoate solvent is selected from one or more of methyl benzoate, ethyl p-methylbenzoate, isobutyl benzoate and ethylhexyl benzoate, and the alkyl-substituted aromatic benzene solvent is selected from one or more of cyclohexylbenzene, 1-hexylbenzene, 1-heptylbenzene, 1-octylbenzene, 1-decylbenzene, 4' -diethylbiphenyl, 3,4' -diisopropylbiphenyl and 4,4' -diisopropylbiphenyl.
13. The organic luminescent ink according to claim 7, wherein: the viscosity of the organic luminous ink at room temperature ranges from 2 cp to 10cp, and the surface tension ranges from 28 mN/m to 40mN/m.
14. An organic light-emitting film, characterized in that: the organic luminescent film comprises the organic luminescent material composition according to any one of claims 1 to 6 or is made of the organic luminescent ink according to any one of claims 7 to 13.
15. The utility model provides an organic electroluminescent device, its includes positive pole, luminescent layer and the negative pole that stacks gradually and sets up, its characterized in that: the luminescent layer comprises the organic luminescent material composition according to any one of claims 1-6 or is made of the organic luminescent ink according to any one of claims 7-13.
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