TWI617648B - 熱活化延遲螢光材料及其在有機電致發光元件中的應用 - Google Patents
熱活化延遲螢光材料及其在有機電致發光元件中的應用 Download PDFInfo
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- TWI617648B TWI617648B TW105140856A TW105140856A TWI617648B TW I617648 B TWI617648 B TW I617648B TW 105140856 A TW105140856 A TW 105140856A TW 105140856 A TW105140856 A TW 105140856A TW I617648 B TWI617648 B TW I617648B
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- 239000000463 material Substances 0.000 title claims abstract description 73
- 230000003111 delayed effect Effects 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 238000005401 electroluminescence Methods 0.000 claims abstract description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052740 iodine Chemical group 0.000 claims abstract description 8
- 239000011630 iodine Chemical group 0.000 claims abstract description 8
- 229910052738 indium Inorganic materials 0.000 claims abstract description 5
- -1 methoxy, ethoxy Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
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- 239000012312 sodium hydride Substances 0.000 description 10
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- 0 CCC(CCC(C)*)NCC(C)CC*(C)(C)** Chemical compound CCC(CCC(C)*)NCC(C)CC*(C)(C)** 0.000 description 5
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- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
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- CUEFUAJNZWXMLR-UHFFFAOYSA-N BrN1C(OC=C1)C1=CC=CC=C1Br Chemical compound BrN1C(OC=C1)C1=CC=CC=C1Br CUEFUAJNZWXMLR-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
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- ONFSYSWBTGIEQE-UHFFFAOYSA-N n,n-diphenyl-4-[2-[4-[2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]ethenyl]aniline Chemical compound C=1C=C(C=CC=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ONFSYSWBTGIEQE-UHFFFAOYSA-N 0.000 description 3
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- JEWIAYIESCUSKQ-UHFFFAOYSA-N 3-bromo-10h-phenothiazine Chemical compound C1=CC=C2SC3=CC(Br)=CC=C3NC2=C1 JEWIAYIESCUSKQ-UHFFFAOYSA-N 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- YXPTXFACOUYRSO-UHFFFAOYSA-N 3,7-dibromo-10h-phenoxazine Chemical group C1=C(Br)C=C2OC3=CC(Br)=CC=C3NC2=C1 YXPTXFACOUYRSO-UHFFFAOYSA-N 0.000 description 1
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002601 lanthanoid compounds Chemical class 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- JNBXWZGMEVQJTH-UHFFFAOYSA-N n,n-diphenylaniline;3-methyl-n-phenylaniline Chemical compound CC1=CC=CC(NC=2C=CC=CC=2)=C1.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 JNBXWZGMEVQJTH-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007725 thermal activation 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
- C07D241/48—Phenazines with hydrocarbon radicals, substituted by nitrogen atoms, directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/28—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom with other substituents attached to the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Abstract
本發明公開了一種熱活化延遲螢光材料及其在有機電致發光元件中的應用。該熱活化延遲螢光材料為具有式I或式Ⅱ通式結構的化合物:
式I,
式Ⅱ,式I和式Ⅱ中,R1為氰基,p為1、2或3,q為1、2或3,m為1或2,n為1或2,Ar1選自C1-6的烷基、甲氧基、乙氧基或苯基中一種以上的基團取代的苯基,Ar2和Ar3選自以下基團:
X為溴或碘。本發明還公開了所述熱活化延遲螢光材料作為有機電致發光元件的發光層的主體材料或發光染料的應用。
Description
本發明屬於材料領域,具體有關一種熱活化延遲螢光材料及其在有機電致發光元件中的應用。
在有機電致發光元件的電致發光過程中,主要依靠有機發光材料從激發態到基態的電子躍遷產生發光。在室溫下,從三線激發態回到基態的電子躍遷產生的發光極微弱,其能量絕大部分以熱的形式損失掉了,發光主要是由單線激發態到基態的電子躍遷產生,稱為電致螢光。由於三線激發態產生的機率為單線激發態的三倍,因此相當於75%的能量沒有被用於發光。充分利用這一能量,將有效地提高有機電致發光元件的發光效率。
為了充分利用發光層主體材料三線激發態的能量,人們曾提出過多種辦法。例如研究和開發高效的磷光摻雜染料並摻雜於主體材料中,使得主體材料的三線態能量有效地傳遞給磷光摻雜染料,然後磷光摻雜染料產生磷光發光,從而使得發光層主體材料三線激發態的能量得到有效利用。該方法所獲得的有機電致發光元件效率高,但材料合成需要銥、鉑等貴重金屬,價格昂貴。還有一種方法是利用鑭系化合物的系間竄越性質,即利用分子內的能量轉移將
發光層主體材料的三線態能量轉移至鑭系金屬離子的4f能級,然後發光等,但目前所得元件效率低。
熱活化延遲螢光(TADF,Thermal active delay fluorescent)是目前非常熱門的一種利用三線態激子能量的方案。例如,Adachi在其文章中報導了熱活化延遲螢光材料,該類材料的三線態能級(T1)與單線態能級(S1)之差(△EST)較小,則三線態能量可以傳輸給單線態能級,並以螢光輻射發光。專利CN 102709485 A中提到,通過在熱延遲螢光主體中摻雜螢光染料來提高元件效率。為了進一步提高能量傳輸複合效率。Adachi等在文章Nature communications 2014「High-efficiency organic light-emitting diodes with fluorescent emitters」中,提出採用一種寬禁帶主體摻雜TADF材料作為輔助染料方案。但在電荷複合過程中,一部分能量直接複合在主體上,主體將單線態能量傳遞給染料。另一部分在輔助染料上複合。文章報導結構,並不能完全有效利用直接在主體複合的能量。同時採用普通主體材料,禁帶寬度大,所需驅動電壓高。
但是,目前的TADF材料存在壽命較短的問題,原因之一是因為三線態壽命太長,容易產生TPA等過程造成激子的淬滅。因此,減少三線態激子的壽命可以有效地提高TADF元件的壽命。
本發明要解決的技術問題是現有技術中的TADF材料存在壽命較短的問題。
為了解決上述技術問題,本發明提供了一種新的TADF材料,其通過在原TADF分子中引入諸如溴或者碘等重原子,可以通過重原子效應提高TADF材料的反向系間竄越和系間竄越等過程從而減少三線態激子的壽命,最終提高元件的壽命。
本發明提供的熱活化延遲螢光材料為具有式I或式Ⅱ通式結構的化合物:
式I,
式Ⅱ,式I和式Ⅱ中,R1為氰基,p為1,2或3,q為1,2或3,m為1或2,n為1或2,Ar1選自C1-6的烷基、甲氧基、乙氧基或苯基中一種以上的基團取代的苯基,Ar2和Ar3選自以下基團:
X為溴或碘。
較佳地,所述熱活化延遲螢光材料為具有如下結構的化合物:
1-1,
1-2,
1-3,
1-4,
1-5,
2-1,
2-2,
2-3,
2-4,
2-5,
2-6,
2-7,
2-8,
2-9。
本發明還提供所述熱活化延遲螢光材料作為有機電致發光元件的發光層的主體材料或發光染料應用。
本發明另提供一種有機電致發光元件,包括發光層,所述發光層包括主體材料和摻雜在主體材料中的發光染料,所述發光染料為上述的熱活化延遲螢光材料。較佳地,所述發光染料在發光層中所占的比例為0.5wt%-10wt%,更佳為5wt%。
作為較佳技術方案,上述的有機電致發光元件,包括在基板上依次沉積彼此層疊的陽極、空穴傳輸層、發光層、電子傳輸層及陰極。
較佳地,所述陽極與空穴傳輸層之間還設有空穴注入層。
本發明還提供一種有機電致發光元件,包括發光層,所述發光層包括主體材料和摻雜在主體材料中的發光染料,所述主體材料為上述的熱活化延遲螢光材料。
較佳地,所述發光染料在發光層中所占的比例為1wt%-10wt%。
本發明能夠達到以下技術效果:本發明提供的TADF材料,其分子中引入諸如溴或者碘等重原子,減少TADF三線態壽命,減少效率滾降,從而提高有機電致發光元件的壽命。
01‧‧‧基板
02‧‧‧陽極
03‧‧‧陰極
04‧‧‧空穴注入層
05‧‧‧空穴傳輸層
06‧‧‧發光層
07‧‧‧電子傳輸層
圖1是本發明的有機電致發光元件的結構示意圖。
下面結合附圖和具體實施例對本發明作進一步說明,以使本領域的技術人員可以更好的理解本發明並能予以實施,但所舉實施例不作為對本發明的限定。
本發明提供的熱活化延遲螢光材料,為具有式I或式Ⅱ通式結構的化合物:
式I,
式Ⅱ,式I和式Ⅱ中,R1為氰基,p為1,2或3,q為1,2或3,m為1或2,n為1或2,Ar1選自C1-6的烷基、甲氧基、乙氧基或苯基中一種以上的基團取代的苯基,Ar2和Ar3選自以下基團:
X為溴或碘。
本發明的熱活化延遲螢光材料通過在TADF分子中引入諸如溴或者碘等重原子,可以通過重原子效應提高TADF材料的反向系間竄越和系間竄越等過程從而減少三線態激子的壽命,最終提高元件的壽命。
具體地,本發明的熱活化延遲螢光材料為如下結構化合物,各化合物的性質及製備方法如下:
式(1-1),△EST=0.16eV
其製備方法:式(1-1)所示結構化合物合成方法:在氮氣範圍下,將3-溴哢唑(5mmol),溶於無水2mL THF中,然後加入氫化鈉(5mmol),混合物在室溫下攪拌30分鐘。隨後,將1,2-二氰基-4,5-二氟基苯(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(1-1),將產物在真空中乾燥。產率:75%。
質譜分析得到的分子量:615.97。
元素分析得到的各元素相對分子質量百分比:C:62.36;H:2.62;N:9.09;Br:25.93。
其製備方法:式(1-2)所示結構化合物合成方法:在氮氣範圍下,將3-溴吩噻嗪(10mmol),溶於無水4mL THF中,然後加入氫化鈉(10mmol),混合物在室溫下攪拌30分鐘。隨後,將2,3,5,6-四氟基腈基苯(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(1-2),將產物在真空中乾燥。產率:62%。
質譜分析得到的分子量:1206.80。
元素分析得到的各元素相對分子質量百分比:C:54.70;H:2.42;N:5.80;S:10.62;Br:26.46。
其製備方法:式(1-3)所示結構化合物合成方法:反應物3-溴吩噻嗪替換為3-溴吩噁嗪,經過與式(1-2)相同的合成方法,得式(1-3)所示結構化合物,產率:59%。
質譜分析得到的分子量:1142.89。
元素分析得到的各元素相對分子質量百分比:C:57.77;H:2.56;N:6.12;O:5.60;Br:27.95。
其製備方法:式(1-4)所示結構化合物合成方法:反應物3-溴吩噻嗪替換為9-對碘苯吩嗪,經過與式(1-2)相同的合成方法,得式(1-4)所示結構化合物,產率:55%。
質譜分析得到的分子量:1631.03。
元素分析得到的各元素相對分子質量百分比:C:58.14;H:3.03;N:7.72;I:31.11。
其製備方法:式(1-5)所示結構化合物合成方法:在氮氣範圍下,將(1,1’-二對溴苯)對氨基苯(15mmol),溶於無水6mL THF中,然後加入氫化鈉(15mmol),混合物在室溫下攪拌30分鐘。隨後,將2,4,6-四氟基-1,3,5-三氰基苯(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到
混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(1-5),將產物在真空中乾燥。產率:31%。
質譜分析得到的分子量:1355.80。
元素分析得到的各元素相對分子質量百分比:C:55.78;H:2.68;N:6.20;Br:35.34。
其製備方法:式(2-1)所示結構化合物合成方法:在氮氣範圍下,將3,6-二溴哢唑基苯(10mmol),溶於無水4mL THF中,然後加入氫化鈉(15mmol),混合物在室溫下攪拌30分鐘。隨後,將1-苯基-1,3,5-三嗪(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(2-1),將產物在真空中乾燥。產率:49%。
質譜分析得到的分子量:955.33。
元素分析得到的各元素相對分子質量百分比:C:56.58;H:2.64;N:7.33;Br:33.46。
其製備方法:式(2-2)所示結構化合物合成方法:在氮氣範圍下,將對溴苯(5mmol),溶於無水4mL THF中,然後加入氫化鈉(5mmol),混合物在室溫下攪拌30分鐘。隨後,將2,4-二(3-聯哢唑)-6-氟基-1,3,5-三嗪(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(2-2),將產物在真空中乾燥。產率:53%。
質譜分析得到的分子量:895.21。
元素分析得到的各元素相對分子質量百分比:C:76.34;H:3.82;N:10.93;Br:8.91。
其製備方法:式(2-3)所示結構化合物合成方法:在氮氣範圍下,將對碘苯(10mmol),溶於無水4mL THF中,然後加入氫化鈉(10mmol),混合物在室溫下攪拌30分鐘。隨後,將2,4-二(3-聯哢唑)-1,3,5-三嗪(1mmol)
加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(2-3),將產物在真空中乾燥。產率:53%。
質譜分析得到的分子量:891.04。
元素分析得到的各元素相對分子質量百分比:C:60.62;H:3.05;N:7.86;I:28.47。
其製備方法:式(2-4)所示結構化合物合成方法:在氮氣範圍下,將二對碘苯-4,4’-二連氨基苯(5mmol),溶於無水4mL THF中,然後加入氫化鈉(5mmol),混合物在室溫下攪拌30分鐘。隨後,將4-氟基-2,6-苯基-1,3,5-三嗪(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(2-4),將產物在真空中乾燥。產率:40%。
質譜分析得到的分子量:1313.93。
元素分析得到的各元素相對分子質量百分比:C:52.08;H:2.91;N:6.39;I:38.61。
其製備方法:式(2-5)所示結構化合物合成方法:反應物3,6-二溴哢唑基苯替換為3,7-二溴吩噁嗪苯,經過與式(2-1)相同的合成方法,得式(2-5)所示結構化合物,產率:61%。
質譜分析得到的分子量:986.87。
元素分析得到的各元素相對分子質量百分比:C:54.74;H:2.55;N:7.09;O:3.24;Br:32.37。
其製備方法:式(2-6)所示結構化合物合成方法:反應物3,6-二溴哢唑基苯替換為3,7-二溴吩噁嗪間苯,經過與式(2-1)相同的合成方法,得式(2-6)所示結構化合物,產率:61%。
質譜分析得到的分子量:1174.82。
元素分析得到的各元素相對分子質量百分比:C:45.99;H:2.14;N:5.96;O:2.72;I:43.19。
其製備方法:式(2-7)所示結構化合物合成方法:在氮氣範圍下,將二溴苯(10mmol),溶於無水4mL THF中,然後加入氫化鈉(10mmol),混合物在室溫下攪拌30分鐘。隨後,將2,4-二氟基-6-(11-苯基-11,12-二氫吲哚並[3,2b]哢唑基)-2,6-苯基-1,3,5-三嗪(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(2-7),將產物在真空中乾燥。產率:34%。
質譜分析得到的分子量:721.03。
元素分析得到的各元素相對分子質量百分比:C:64.93;H:3.21;N:9.71;Br:22.15。
其製備方法:式(2-8)所示結構化合物合成方法:在氮氣範圍下,將6-苯基-2,9-二碘-吲哚並[2,3a]哢唑(10mmol),溶於無水4mL THF中,然後加入氫化鈉(10mmol),混合物在室溫下攪拌30分鐘。隨後,將6-氟基-2,4-二苯基-1,3,5-三嗪(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加
入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(2-8),將產物在真空中乾燥。產率:31%。
質譜分析得到的分子量:815.44。
元素分析得到的各元素相對分子質量百分比:C:57.44;H:2.84;N:8.59;I:31.13。
其.製備方法:式(2-9)所示結構化合物合成方法:在氮氣範圍下,將11-對溴苯基-吲哚並[2,3a]哢唑(7mmol),溶於無水4mL THF中,然後加入氫化鈉(10mmol),混合物在室溫下攪拌30分鐘。隨後,將6-氟基-2,4-二對溴苯基-1,3,5-三嗪(1mmol)加入反應瓶中,繼續攪拌1小時。最後將2mL冷水加入到混合物中將反應淬滅。待混合物冷卻至室溫後,通過真空抽濾,接著通過柱色譜提純產物式(2-9),將產物在真空中乾燥。產率:36%。
質譜分析得到的分子量:800.34。
元素分析得到的各元素相對分子質量百分比:C:58.53;H:2.77;N:8.75;Br:29.95。
本發明的熱活化延遲螢光材料可用作有機電致發光元件發光層的發光染料。
如圖1所示,本發明的有機電致發光元件包括在基板01上依次沉積彼此層疊的陽極02、空穴注入層04、空穴傳輸層05、發光層06、電子傳輸層07及陰極03。
其中發光層06的材料包括主體材料和摻雜在主體材料中的發光染料,發光材料為具有式I結構或式Ⅱ結構的化合物。
本發明的有機發光顯示元件實施例:陽極02可以採用無機材料或有機導電聚合物。無機材料一般為氧化銦錫(ITO)、氧化鋅(ZnO)、氧化銦鋅(IZO)等金屬氧化物或金、銅、銀等功函數較高的金屬,較佳ITO;有機導電聚合物較佳為聚噻吩/聚乙烯基苯磺酸鈉(以下簡稱PEDOT/PSS)、聚苯胺(以下簡稱PANI)中的一種。
陰極03一般採用鋰、鎂、鈣、鍶、鋁、銦等功函數較低的金屬或它們與銅、金、銀的合金,或金屬與金屬氟化物交替形成的電極層。本發明中陰極較佳為層疊的LiF層和Al層(LiF層在外側)。
空穴傳輸層05的材料可以選自芳胺類和枝聚物類低分子材料,較佳NPB。
電子傳輸層07的材料可採用有機金屬配合物(如Alq3、Gaq3、BAlq或Ga(Saph-q))或其他常用於電子傳輸層的材料,如芳香稠環類(如pentacene、苝)或鄰菲咯啉類(如Bphen、BCP)化合物。
本發明的有機電致發光元件還可在陽極02和空穴傳輸層05之間具有空穴注入層04,所述空穴注入層04的材料例如可採用4,4',4''-三(3-甲基苯基苯胺)三苯胺摻雜F4TCNQ,或者採用銅酞菁(CuPc),或可為金屬氧化物類,如氧化鉬,氧化錸。
上述各層的厚度可採用本領域中這些層常規的厚度。
本發明還提供所述有機電致發光元件的製備方法,包括在基板01上依次沉積彼此層疊的陽極02、空穴注入層04、空穴傳輸層05、發光層06、電子傳輸層07及陰極03,然後封裝。
基板可以是玻璃或是柔性基片,所述柔性基片可採用聚酯類、聚醯亞胺類化合物材料或者薄金屬片。所述層疊及封裝可採用本領域技術人員已知的任意合適方法。
對比例1:
本對比例以ITO(氧化銦錫)作為陽極;以NPB作為空穴注入層;以TCTA作為空穴傳輸層;發光層採用CBP作為主體材料,DSA-Ph為發光染料,在發光層中摻雜的質量百分比為5wt%);Bphen作為電子傳輸層;LiF(5nm)/Al作為陰極。結構如下:ITO/NPB(40nm)/TCTA(10nm)/CBP:5wt% DSA-Ph(30nm)/Bphen(40nm)/LiF(5nm)/Al
對比例2:
本對比例的結構與對比例1的區別僅在於發光層採用的發光染料為2CzPN:ITO/NPB(40nm)/TCTA(10nm)/CBP:5wt% 2CzPN(30nm)/Bphen(40nm)/LiF(5nm)/Al
實施例1
本實施例的結構與對比例1的區別僅在於發光層採用的發光染料為本發明的化合物1-1:
1-1
ITO/NPB(40nm)/TCTA(10nm)/CBP:5wt%化合物1-1(30nm)/Bphen(40nm)/LiF(5nm)/Al
實施例1的TADF材料由於引入了重原子,重原子效應提高TADF材料的反向系間竄越和系間竄越等過程從而減少三線態激子的壽命,最終提高元件的壽命。
實施例2~5
實施例2~5的結構與實施例1的區別僅在於發光層中發光染料化合物1-1摻雜濃度不同:ITO/NPB(40nm)/TCTA(10nm)/CBP:0.5~10wt%化合物1-1(30nm)/Bphen(40nm)/LiF(5nm)/Al
設計不同的摻雜濃度實施例
從上表看出,發光染料濃度的增加導致了元件的電流效率先增後減,在摻雜濃度為5wt%時元件的電流效率最高,元件的電壓基本無明顯改變,但元件的壽命隨著發光染料摻雜濃度的提高而增加。
實施例6
本實施例中的OLED結構與實施例1的區別僅在於發光層中摻雜不同的具有式I或式Ⅱ結構的化合物作為發光染料:ITO/NPB(40nm)/TCTA(10nm)/CBP:5wt%(具有式I或式Ⅱ結構的化合物)(30nm)/Bphen(40nm)/LiF(5nm)/Al
從上表看出,本發明所保護的含有溴或碘重原子的熱活化延遲螢光材料元件壽命均增加了,這是因為通過重原子效應提高TADF材料的反向系間竄越和系間竄越等過程從而減少三線態激子的壽命,最終提高元件的壽命。
實施例7~9
本實施例中的OLED結構與實施例1的區別在於發光層中的主體材料為化合物2-2,發光染料為Ir(ppy)3。Ir(ppy)3摻雜濃度(在發光層中所占的重量百分比)為1~10wt%。
ITO/NPB(40nm)/TCTA(10nm)/化合物2-2:1~10wt% Ir(ppy)3(30nm)/Bphen(40nm)/LiF(5nm)/Al。
對比例3
本對比例的結構與實施例7~9的區別僅在於發光層採用的主體材料為CBP:
ITO/NPB(40nm)/TCTA(10nm)/CBP:5wt% Ir(ppy)3(30nm)/Bphen(40nm)/LiF(5nm)/Al。
對比例4
本對比例的結構與實施例7~9的區別僅在於發光層採用的主體材料為CC2TA:
CC2TA
從上表看出,對比三種不同摻雜濃度的實施例7,實施例8和實施例9,元件的電學性能隨發光染料的摻雜濃度的提高先升後降,在5wt%的摻雜濃度時達到最優,但是元件壽命隨染料的摻雜濃度的提高而提高。另外,本發明所保護的含有溴重原子的熱活化延遲螢光材料做主體的元件壽命均比傳統主體CBP做主體的元件(對比例3)壽命高,與相同結構但是不帶重原子的熱活化敏化螢光材料做主體的元件(對比例4)對比,電學性能並沒有很大區別,但是實施例7的元件壽命比對比例4的元件壽命要高,這是由於重原子效應提高了TADF材料的反向系間竄越係數,從而減少三線態激子的壽命,最終提高元件的壽命。
以上所述實施例僅是為充分說明本發明而所舉的較佳的實施例,本發明的保護範圍不限於此。本技術領域的技術人員在本發明基礎上所作的等同替代或變換,均在本發明的保護範圍之內。本發明的保護範圍以申請專利範圍為準。
01‧‧‧基板
02‧‧‧陽極
03‧‧‧陰極
04‧‧‧空穴注入層
05‧‧‧空穴傳輸層
06‧‧‧發光層
07‧‧‧電子傳輸層
Claims (8)
- 一種熱活化延遲螢光材料,其特徵在於,所述熱活化延遲螢光材料為具有式I或式Ⅱ通式結構的化合物:
- 根據請求項1所述的熱活化延遲螢光材料,其中,所述熱活化延遲螢光材料為具有如下結構的化合物:
- 一種請求項1或2所述的熱活化延遲螢光材料的應用,其特徵在於,所述熱活化延遲螢光材料作為有機電致發光元件的發光層的主體材料或發光染料應用。
- 一種有機電致發光元件,包括發光層,其中,所述發光層包括主體材料和摻雜在主體材料中的發光染料,所述發光染料為請求項1或2所述的熱活化延遲螢光材料,所述發光染料在發光層中所占的比例為0.5wt%-10wt%。
- 根據請求項4所述的有機電致發光元件,其中,所述發光染料在 發光層中所占的比例為5wt%。
- 根據請求項4所述的有機電致發光元件,其中,包括在基板上依次沉積彼此層疊的陽極、空穴傳輸層、發光層、電子傳輸層及陰極。
- 根據請求項6所述的有機電致發光元件,其中,所述陽極與空穴傳輸層之間還設有空穴注入層。
- 一種有機電致發光元件,包括發光層,其中,所述發光層包括主體材料和摻雜在主體材料中的發光染料,所述主體材料為請求項1或2所述的熱活化延遲螢光材料,所述發光染料在發光層中所占的比例為1wt%-10wt%。
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