CN112750957B - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN112750957B CN112750957B CN202110004228.8A CN202110004228A CN112750957B CN 112750957 B CN112750957 B CN 112750957B CN 202110004228 A CN202110004228 A CN 202110004228A CN 112750957 B CN112750957 B CN 112750957B
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- electroluminescent device
- organic electroluminescent
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- 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 1
- 239000005725 8-Hydroxyquinoline Chemical class 0.000 description 1
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- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
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- DVNOWTJCOPZGQA-UHFFFAOYSA-N 9-[3,5-di(carbazol-9-yl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 DVNOWTJCOPZGQA-UHFFFAOYSA-N 0.000 description 1
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- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 229910052772 Samarium Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052769 Ytterbium Inorganic materials 0.000 description 1
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- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 description 1
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- 230000009471 action Effects 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
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- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical class C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
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- 229910052788 barium Inorganic materials 0.000 description 1
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- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
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- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 125000005566 carbazolylene group Chemical group 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 239000011147 inorganic material Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 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 description 1
- 239000002346 layers by function Substances 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
- MORCTKJOZRLKHC-UHFFFAOYSA-N lithium;oxoboron Chemical compound [Li].O=[B] MORCTKJOZRLKHC-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- CWIUXGVIFIAHGZ-UHFFFAOYSA-N n-[4-[4-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 CWIUXGVIFIAHGZ-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
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- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 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
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/856—Arrangements for extracting light from the devices comprising reflective means
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic electroluminescent device, and relates to the technical field of organic electroluminescence. The cover layer in the organic electroluminescent device provided by the invention comprises the first cover layer and the second cover layer, and compared with the traditional single-layer cover layer organic electroluminescent device, the combination of two materials with different refractive indexes can better reduce total reflection loss, thereby improving the luminous efficiency of the organic electroluminescent device and ensuring good stability of the film. The organic electroluminescent device has good application effect and industrialization prospect, and can be widely applied to the fields of panel display, illumination light sources, organic solar cells, organic photoreceptors or organic thin film transistors and the like.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device.
Background
An organic light-emitting diode (OLED) is an all-solid-state light-emitting device, and has advantages of light weight, high efficiency, low power consumption, flexibility, simple manufacturing process, etc., and has been used in the fields of mobile phones and televisions. At the same time, OLEDs are beginning to penetrate increasingly into the fields of automobiles, virtual Reality (VR), and health lighting, among others, highlighting their irreplaceable superior properties. Taking healthy illumination as an example, the OLED integrating the advantages of light weight, thinness, softness, no blue light hazard, low glare and the like is praised as a fourth light source revolution product.
The light emitting principle of the OLED is that electrons and holes are injected into the device from the cathode and anode, respectively, by applying a direct current to the cathode and anode, carriers migrate in the auxiliary transport material under the action of an electric field, meet in the light emitting layer to generate excitons, and the exciton radiation transitions back to the ground state and emits light. Organic electroluminescent devices can be classified into bottom emission and top emission according to the direction of light emission. In the bottom emission device, light is emitted from the substrate, the reflective electrode is over the organic light emitting layer, and the transparent electrode is under the organic light emitting layer. The light of the thin film transistor part in bottom emission cannot pass through, and the light emitting area becomes smaller. In the top emission device, the transparent electrode is on the organic light emitting layer, and the reflective electrode is under the organic light emitting layer, so that light is emitted from the opposite direction of the substrate, thereby increasing the light transmission area. So that the application now dominates over top-emitting devices. In order to improve the light emitting efficiency of the top emission organic light emitting diode, the simplest and effective method is to form a cover layer as a light extraction functional layer on a transparent electrode, adjust the optical interference distance, suppress external light reflection, suppress extinction reaction caused by surface plasmon movement, and the like.
The coating material has good heat conductivity, light transmittance, corrosion resistance, mechanical strength, adhesion with a substrate and the like. According to the properties of materials, inorganic materials and organic materials are generally classified, and organic materials are widely used with advantages of low cost and convenience in processing. According to the report of the prior literature, the organic coating layer mostly selects amine derivative materials with high refractive index, the structure has certain steric hindrance, the materials are not easy to crystallize after being heated and cooled, and the chemical properties are stable. However, in the conventional organic electroluminescent device, a single-layer coating is often used, so that total reflection loss cannot be well reduced, and thus the improvement range of luminous efficiency is not very large, so that the organic electroluminescent device made of a coating material with reasonable and excellent performance is an urgent problem to be solved.
Disclosure of Invention
The invention aims to solve the technical problems in the prior art and provides an organic electroluminescent device which has good luminous efficiency.
In order to solve the above technical problems. The invention provides an organic electroluminescent device, which sequentially comprises an anode electrode, an organic layer, a cathode electrode and a cover layer, wherein the cover layer comprises a first cover layer and a second cover layer, the refractive index of the first cover layer at 450-630 nm is 1.4-1.8, and the refractive index of the second cover layer at 450-630 nm is 1.9-3.0; the first capping layer comprises a silicon-containing triarylamine compound represented by formula I,
Wherein A is selected from one of the formulas (1) - (3):
r is the same or different and is selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
Ar a one selected from the group consisting of substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, wherein- - -is a single bond or none;
L a 、L b independently selected from one of single bond, substituted or unsubstituted C6-C25 arylene, and substituted or unsubstituted C2-C20 heteroarylene;
R a identically or differently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent two R a The groups bond to form a ring structure;
R b identically or differently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent two R b The groups bond to form a ring structure;
r is 0, 1, 2, 3 or 4; a is 0, 1, 2, 3 or 4; b is 0, 1, 2, 3 or 4.
The invention has the beneficial effects that:
the invention provides an organic electroluminescent device which sequentially comprises an anode electrode, a hole injection layer, a hole transmission layer, a light-emitting layer, an electron transmission layer, an electron injection layer, a cathode electrode and a cover layer, wherein the cover layer comprises a first cover layer and a second cover layer, compared with the traditional single-layer cover layer organic electroluminescent device, the combination of two materials with different refractive indexes can better reduce total reflection loss and improve light extraction efficiency, so that the light-emitting efficiency of the organic electroluminescent device is improved.
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.
The alkyl group according to the present invention is a hydrocarbon group having at least one hydrogen atom in the alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
Cycloalkyl as used herein refers to a hydrocarbon group having at least one hydrogen atom in the cycloparaffin molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 3 to 6 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, etc., but are not limited thereto. The alkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, or a norbornyl group.
Aryl in the context of the present invention means that after removal of one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, a monovalent radical is left, which may be a monocyclic aryl group, a polycyclic aryl group or a fused ring aryl group, preferably having from 6 to 25 carbon atoms, more preferably from 6 to 20 carbon atoms, particularly preferably from 6 to 14 carbon atoms. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but is not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, for example, but not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirobifluorenyl, and the like. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthryl group (preferably a 2-anthryl group), a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylenyl group, or a spirobifluorenyl group.
Heteroaryl according to the present invention refers to the generic term for groups in which one or more aromatic nucleus carbon atoms in the aryl group are replaced by heteroatoms, including but not limited to oxygen, sulfur, nitrogen or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms, the attachment site of the heteroaryl group may be located on a ring-forming carbon atom or on a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl, a polycyclic heteroaryl or a fused ring heteroaryl. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl, and the like; the polycyclic heteroaryl group includes bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, and the like. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a benzodibenzothienyl group, a benzodibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.
The arylene group according to the present invention means a generic term for divalent groups remaining after removal of two hydrogen atoms from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms. The monocyclic arylene group includes phenylene and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, etc., but is not limited thereto; the condensed ring arylene includes, but is not limited to, naphthylene, anthrylene, phenanthrylene, fluorenylene, pyreylene, triphenylene, fluoranthenylene, phenylenedenyl, and the like. The arylene group is preferably phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, or phenylenediyl.
Heteroaryl, as used herein, refers to the generic term for groups in which one or more of the aromatic nucleus carbons in the arylene group is replaced with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably having from 6 to 25 carbon atoms, more preferably from 6 to 20 carbon atoms, particularly preferably from 6 to 15 carbon atoms, the heteroarylene group may be attached to a ring-forming carbon atom or to a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group or a fused ring heteroarylene group. The monocyclic heteroarylene group includes, but is not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thienyl group, and the like; the polycyclic heteroarylene group includes bipyridylene group, bipyrimidiylene group, phenylpyridylene group, etc., but is not limited thereto; the condensed ring heteroarylene group includes quinolinylene, isoquinolylene, indolylene, benzothienyl, benzofuranylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofuranylene, benzodibenzofuranylene, dibenzothiophenylene, benzodithiorenylene, carbazolylene, benzocarbazolylene, acridinylene, 9, 10-dihydroacridinylene, phenoxazinylene, phenothiazinylene, phenoxazinylene, and the like, but is not limited thereto. The heteroaryl group is preferably a pyridyl group, a pyrimidylene group, a thienyl group, a furanylene group, a benzothienyl group, a benzofuranylene group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzodibenzothiophenyl group, a benzodibenzofuranyl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.
"substituted …" as used herein, such as substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene refers to a group that is mono-or poly-substituted with, but not limited to, a group selected independently from deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted amine, and the like, preferably a group selected from deuterium, methyl, ethyl, isopropyl, t-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, benzophenyl, perylene, pyrenyl, benzyl, fluorenyl, 9-dimethylfluorenyl, diphenylamino, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophenyl, phenoxazinyl, or poly-substituted with a group selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenylenyl, fluorenyl, thiophenyl, phenanthrenyl, or poly-substituted with a group.
The bonding together to form a cyclic structure as used herein means that the two groups are attached to each other by chemical bonds and optionally aromatized. As exemplified below:
In the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a condensed ring, for example, phenyl, naphthyl, cyclopentenyl, cyclopentanyl, cyclohexanephenyl, quinolinyl, isoquinolinyl, dibenzothienyl, phenanthryl or pyrenyl, but is not limited thereto.
The term "refractive index" as used herein means a refractive index at 450nm to 630nm, particularly a refractive index at 450nm to 550nm, particularly a refractive index at 450 nm. Preferably, the "refractive index" as used herein refers to a refractive index at 450nm,550nm or 630nm, and more preferably, the "refractive index" as used herein refers to a refractive index at 450 nm.
The organic electroluminescent device has the structure of a substrate/an anode/an organic layer/a cathode/a covering layer. In the present invention, the organic layer includes one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a charge generation layer, a light emitting auxiliary layer, and the like. In the invention, the covering layer comprises a first covering layer and a second covering layer; wherein the first cover layer is located between the cathode and the second cover layer, or the second cover layer is located between the cathode and the first cover layer. The organic electroluminescent device of the invention is preferably:
A substrate/anode/hole transport layer/light emitting layer/electron transport layer/cathode/second cover layer/first cover layer;
a substrate/anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/second capping layer/first capping layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/second capping layer/first capping layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/first cover layer/second cover layer;
a substrate/anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/second capping layer/first capping layer;
the substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode/second capping layer/first capping layer.
However, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the device parameter requirement and the material characteristics, and partial organic layers can be added or omitted. For example, an electron blocking layer may be provided between the hole transporting layer and the light emitting layer, a hole blocking layer may be provided between the electron transporting layer and the light emitting layer, and an organic layer having the same function may be formed in a stacked structure of two or more layers.
The light emitting device of the present invention is generally formed on a substrate. The substrate may be a substrate made of glass, plastic, polymer film, silicon, or the like, as long as it is not changed when an electrode is formed or an organic layer is formed. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.
At least one of the anode and the cathode of the light-emitting device of the present invention is transparent or translucent, and preferably, the light-emitting device of the present invention is transparent or translucent on the cathode side.
The anode material is generally preferably a material having a large work function so that holes are smoothly injected into the organic material layer, and a conductive metal oxide film, a semitransparent metal thin film, or the like is often used. For example, a film (NESA or the like) made of a conductive inorganic compound such as indium oxide, zinc oxide, tin oxide, indium tin oxide (abbreviated as ITO) or indium zinc oxide (abbreviated as IZO) as a composite thereof, or gold, platinum, silver, copper or the like is used, and examples of the production method include vacuum vapor deposition, sputtering, ion plating, and the like. As the anode, an organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof, or the like can be used. The anode may have a laminate structure of 2 or more layers, and preferably, a transparent ITO substrate is used for the anode of the present invention.
The hole injection layer is to improve efficiency of injecting holes from the anode into the hole transport layer and the light emitting layer. The hole injection material of the present invention may be a metal oxide such as molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, or titanium oxide, a low molecular organic compound such as a phthalocyanine compound or a polycyano-containing conjugated organic material, but is not limited thereto. The hole injection layer of the present invention may have a single structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances.
The hole transport layer is a layer having a function of transporting holes. The hole transport material of the present invention is preferably a material having a good hole transport property, and may be selected from polymer materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, and the like, and poly-p-phenylene derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, but not limited thereto. The hole transport layer of the present invention may have a single structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances.
The light-emitting layer is a layer having a light-emitting function. As for the light emitting layer of the organic electroluminescent device of the present invention, a red light emitting material, a green light emitting material, or a blue light emitting material may be used as the light emitting material, and two or more light emitting materials may be mixed and used as necessary. The light-emitting material may be a host material alone or a mixture of a host material and a dopant material, and the light-emitting layer is preferably a mixture of a host material and a dopant material.
Preferably, the host material of the present invention is selected from 4,4' -bis (9-carbazole) biphenyl (abbreviation: CBP), 9, 10-bis (2-naphthyl) anthracene (abbreviated as ADN), 4-bis (9-carbazolyl) biphenyl (abbreviated as CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (abbreviated as mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (abbreviated as TCTA), 9, 10-bis (1-naphthyl) anthracene (abbreviated as α -AND), N ' -bis- (1-naphthyl) -N, N ' -diphenyl- [1,1':4',1":4",1 '" -tetrabenzo ] -4, 4' "-diamine (abbreviated as 4P-NPB), 1,3, 5-tris (9-carbazolyl) benzene (abbreviated as TCP), etc., which may be a single layer structure composed of a single substance, or a single layer structure or a multi-layer structure formed of different substances, the above materials may further include other known materials suitable for the light emitting layer, such as a green light emitting layer represented by the following GH-12-host layer, for example:
The light emitting layer guest material of the present invention may include one material or a mixture of two or more materials, and the light emitting material is classified into a blue light emitting material, a green light emitting material, and a red light emitting material. Preferably, the luminescent material of the invention is green luminescent material, and the green luminescent layer object is selected from tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)) and the like. In addition to the above materials, the light-emitting layer guest material may include other known materials suitable for use as a light-emitting layer, such as green light-emitting layer guest materials represented by GD-1 to GD-10 as follows:
the doping ratio of the host material and the guest material of the light-emitting layer may be varied depending on the materials used, and is usually 0.01 to 20% by mass, preferably 0.1 to 15% by mass, and more preferably 1 to 10% by mass.
The electron transport layer is a layer having a function of transporting electrons, and functions to inject electrons and balance carriers. The electron transport material of the present invention may be selected from known oxadiazole derivatives, anthraquinone dimethanes and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinone dimethanes and derivatives thereof, fluorenone derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and metal complexes of derivatives thereof, and the electron transport layer of the present invention may have a single structure formed of a single material, or may have a single structure or a multilayer structure formed of different materials. In addition to the above materials, the electron transport layer material may include other known materials suitable for use as an electron transport layer. Preferably, the electron transport layer of the present invention is selected from the group consisting of a mixture of one or more of the following compounds:
The film thickness of the hole transport layer and the electron transport layer may be selected depending on the material used, and may be selected so as to have a suitable value for the driving voltage and the luminous efficiency, but it is not preferable that the film thickness does not cause pinholes at least, and if the film thickness is too large, the driving voltage of the device is increased. Therefore, the film thickness of the hole transport layer and the electron transport layer is, for example, 1nm to 1. Mu.m, preferably 2nm to 500nm, more preferably 5nm to 200nm.
The electron injection layer material is a material that assists electron injection from the cathode into the organic layer. The best choice for this material is typically corrosion resistant, high work function metals as cathodes, with commonly used materials being Al and Ag. Electron injecting materials have evolved to date to include two classes; one is an alkali metal compound, such as lithium oxide (Li 2 O), lithium boron oxide (LiBO) 2 ) Cesium carbonate (Cs) 2 CO 3 ) Potassium silicate (K) 2 SiO 3 ) And the like, the optimal thickness is generally 0.3-1.0 nm, and the device formed by the compound can reduce the driving voltage and improve the device efficiency. In addition, an acetate Compound (CH) 3 COOM, where M is Li, na, K, rb, cs) also has a similar effect. The other is alkali metal fluoride (MF, where M is Li, na, K, rb, cs), and if Al is used as the cathode material, these materials are typically less than 1.0nm thick at best. The electron injection layer according to the present invention may be selected from LiF.
A cathode material is generally preferably a metal material having a small work function in order to inject electrons into the electron injection/transport layer or the light-emitting layer. For example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, or an alloy of 2 or more of them, or an alloy of 1 or more of them with 1 or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, or a graphite interlayer compound, etc. can be used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The cathode may have a laminate structure of 2 or more layers. The cathode may be prepared by forming a thin film of these electrode materials by vapor deposition, sputtering, or the like. Among them, when light emission of the light emitting layer is taken out from the cathode, the light transmittance of the cathode is preferably more than 10%. The sheet resistivity of the cathode is preferably hundreds Ω/≡or less, and the film thickness is usually 10nm to 1 μm, preferably 50 to 200nm.
Preferably, the cathode of the present invention adopts Ag or Mg-Ag alloy or thin Al.
The cladding material is to reduce total emission loss and waveguide loss in the OLED device and to improve light extraction efficiency. The cover layer comprises a first cover layer and a second cover layer, wherein the refractive index of the first cover layer at 450-630 nm is 1.4-1.8, and the refractive index of the second cover layer at 450-630 nm is 1.9-3.0; the first capping layer comprises a silicon-containing triarylamine compound represented by formula I,
wherein A is selected from one of the formulas (1) - (3):
r is the same or different and is selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
Ar a one selected from the group consisting of substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, wherein- - -is a single bond or none;
L a 、L b independently selected from single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C20One of heteroarylene groups;
R a identically or differently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent two R a The groups bond to form a ring structure;
R b identically or differently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent two R b The groups bond to form a ring structure;
r is 0, 1, 2, 3 or 4; a is 0, 1, 2, 3 or 4; b is 0, 1, 2, 3 or 4.
Preferably, the Ar a One selected from the following groups:
wherein R is 12 One of methyl, n-propyl, n-butyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl and naphthyl;
R p one selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl;
q is 0, 1 or 2;
L c Selected from one of the following formulas:
preferably, L a Selected from single bond or one of the following groups:
preferably, R a And R is b Independently selected from one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, phenyl, pentadeuterated phenyl, tolyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, 9-diphenylfluorenyl, spirofluorenyl;
r is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, perylenyl, pyrenyl, benzyl, fluorenyl, 9-dimethylfluorenyl, carbazolyl, 9-phenylcarbazolyl, acridinyl, dibenzofuranyl, dibenzothiophenyl.
Preferably, the silicon-containing triarylamine compound represented by formula I is selected from any one of the chemical structures shown in the following:
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preferably, the second cover layer contains a spirofluorene-containing triarylamine compound represented by the following formula ii:
wherein R is 1 、R 2 、R 3 Independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
L 1 、L 2 、L 3 Independently selected from one of single bond, substituted or unsubstituted C6-C25 arylene, and substituted or unsubstituted C2-C20 heteroarylene;
X 1 selected from O, S or NR 0 Wherein R is 0 One selected from the group consisting of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, and a substituted or unsubstituted C2-C20 heteroaryl group;
R 4 one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl;
x is selected from O, S, NR 00 Or CR (CR) 11 R 11 Wherein R is 00 One selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, R 11 Identically or differently selected from hydrogen, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroarylOne of the bases;
R 5 one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl;
m is selected from 0, 1, 2, 3 or 4; n is selected from 0, 1, 2, 3 or 4; p is selected from 0, 1, 2, 3 or 4; q is selected from 0, 1, 2, 3 or 4; o is selected from 0, 1, 2, 3 or 4;
When m is greater than 1, each R 1 Identical or different, adjacent R' s 1 Can form benzene ring; when n is greater than 1, each R 2 Identical or different, adjacent R' s 2 Can form benzene ring; when p is greater than 1, each R 3 Identical or different, adjacent R' s 3 Can form benzene ring; when q is greater than 1, each R 4 Identical or different, adjacent R' s 4 Can form benzene ring or naphthalene ring; when o is greater than 1, each R 5 Identical or different, adjacent R' s 5 Can be benzene ring.
Preferably, said R 1 、R 2 、R 3 Independently selected from one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, phenyl, pentadeuterated phenyl, tolyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, 9-diphenylfluorenyl, spirofluorenyl;
m is selected from 0, 1 or 2; n is selected from 0, 1 or 2; p is selected from 0, 1 or 2.
Preferably, the X 1 Selected from O, S or NR 0 Wherein R is 0 One selected from methyl, ethyl, isopropyl, tertiary butyl, cyclohexyl, phenyl, tolyl, biphenyl and naphthyl; q is selected from 0, 1, 2, 3 or 4;
R 4 selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl or one of the following substituents:
Preferably, the saidOne selected from the following groups: />
Preferably, said R 5 One of the following substituents is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, camphene, norbornyl or the like:
x is selected from O, S, NR 00 Or CR (CR) 11 R 11 Wherein R is 00 One selected from phenyl, pentadeuterated phenyl, tolyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl and fluorenyl, R 11 The two groups are selected from one of hydrogen, phenyl, pentadeuterated phenyl, tolyl, biphenyl, terphenyl and naphthyl identically or differently;
o is selected from 0, 1 or 2.
Preferably, the L 1 、L 2 、L 3 Independently selected from a single bond or any one of the following groups:
preferably, the triarylamine compound containing spirofluorene represented by formula II is selected from any one of the chemical structures shown in the following:
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the order of the layers to be laminated, the number of layers, and the thickness of each layer can be appropriately selected in consideration of the luminous efficiency and the lifetime of the device.
The method for preparing and forming each layer in the organic electroluminescent device is not particularly limited, and any one of vacuum evaporation method, spin coating method, vapor deposition method, blade coating method, laser thermal transfer method, electrospray coating method, slit coating method, and dip coating method may be used, and in the present invention, a vacuum evaporation method is preferably used.
In the organic electroluminescent device according to the present invention, the cover layer includes a first cover layer and a second cover layer, which may be formed into a film alone or may be mixed with other materials to form a film. Preferably, the sum of the thicknesses of the first cover layer and the second cover layer is 30nm to 120nm. The evaporation of the first cover layer and the second cover layer may be performed sequentially, the first cover layer may be evaporated, the second cover layer may be evaporated, or the second cover layer may be evaporated, and the first cover layer may be evaporated.
The organic electroluminescent device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, indication boards, signal lamps and the like.
The silicon-containing triarylamine compound represented by the formula I and the spirofluorene-containing triarylamine compound represented by the formula II can be obtained by the following methods:
the silicon-containing triarylamine compound shown in the formula I can be obtained through a Buch-Wald reaction, namely, raw materials, a catalyst, organic base, a ligand and a solution are added in the nitrogen atmosphere, and the corresponding compound is obtained through the reaction at a corresponding temperature.
The triarylamine compound containing spirofluorene represented by the formula II can be obtained through a Buch-Ward reaction, namely, raw materials, a catalyst, organic base, a ligand and a solution are added in the nitrogen atmosphere, and the corresponding compound is obtained through the reaction at a corresponding temperature.
The source of the raw materials used in the above-mentioned various reactions is not particularly limited in the present invention, and the compounds represented by the formula I and the formula II according to the present invention may be obtained using commercially available raw materials or using a preparation method well known to those skilled in the art.
The present invention is not particularly limited to the above reaction, and conventional reactions well known to those skilled in the art may be employed.
The present invention is explained more fully by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue burden.
Description of the starting materials, reagents and characterization equipment:
the source of the raw materials used in the following examples is not particularly limited and may be commercially available products or prepared by a preparation method well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis was carried out using a Vario EL cube organic elemental analyzer from Elementar, germany, and the sample mass was 5 to 10mg.
EXAMPLE 1 Synthesis of Compound 1-1
Step1: synthetic intermediate A-1
To a 1L reaction flask were successively added toluene (600 mL), a-1 (20.00 g,0.06 mol), b-1 (17.35 g,0.06 mol), palladium acetate (0.21 g,0.95 mmol), sodium t-butoxide (11.53 g,0.12 mol) and tri-t-butylphosphine (8 mL of toluene solution) under nitrogen. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give intermediate a-1 (25.03 g, 77% yield) as a recrystallized solid, which was > 99.6% pure by HPLC.
Step2: synthesis of Compound 1-1
Toluene solvent (600 ml), c-1 (9.32 g,40 mmol), intermediate A-1 (21.67 g,40 mmol) and Pd were added sequentially to a 1L reactor under nitrogen 2 (dba) 3 (366 mg,0.40 mmol), BINAP (0.67 g,1.08 mmol) and sodium tert-butoxide (4.81 g,50 mmol) were dissolved by stirring and reacted under reflux for 24 hours under the protection of nitrogen, after the reaction was completed, the reaction solution was washed with dichloromethane and distilled water and extracted by liquid separation. For organic layersDried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, and cyclohexane was used: ethyl acetate=9:1 is used as an eluent for column chromatography separation, purification and refining, and finally the compound 1-1 (18.32 g, yield 66%) is obtained, and the purity of the solid detected by HPLC is not less than 99.4%.
Mass spectrum m/z:693.2898 (theory: 693.2852). Theoretical element content (%) C 51 H 39 NSi: c,88.27; h,5.66; n,2.02 measured element content (%): c,88.28; h,5.63; n,2.06.
EXAMPLE 2 Synthesis of Compounds 1-13
By the method of the above compound 1-1, compound 1-13 (18.97 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:667.2713 (theory: 667.2695). Theoretical element content (%) C 49 H 37 NSi: c,88.11; h,5.58; n,2.10 measured element content (%): c,88.14; h,5.55; n,2.10.
EXAMPLE 3 Synthesis of Compounds 1-17
By the method of the above compound 1-1, compound 1-17 (18.97 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:707.2686 (theory: 707.2644). Theoretical element content (%) C 51 H 37 NOSi: c,86.53; h,5.27; n,1.98 measured element content (%): c,86.55; h,5.28; n,1.95.
EXAMPLE 4 Synthesis of Compounds 1-38
By the method of compound 1-1 described above, compound 1-38 (18.17 g) was synthesized and the solid purity was ≡ 99.3% by HPLC. Mass spectrum m/z:698.3198 (theory: 698.3166). Theoretical element content (%) C 51 H 34 D 5 NSi: c,87.63; h,6.34; n,2.00 measured element content (%): c,87.65; h,6.32; n,1.98.
EXAMPLE 5 Synthesis of Compounds 1-45
By the method of the above compound 1-1, compound 1-45 (21.33 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:783.3359 (theory: 783.3321). Theoretical element content (%) C 58 H 45 NSi: c,88.85; h,5.79; n,1.79 measured element content (%): c,88.87; h,5.78；N，1.72。
EXAMPLE 6 Synthesis of Compounds 1-50
By the method of the above compound 1-1, compound 1-50 (21.63 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:857.3543 (theory: 857.3478). Theoretical element content (%) C 64 H 47 NSi: c,89.57; h,5.52; n,1.63 measured element content (%): c,89.55; h,5.54; n,1.68.
EXAMPLE 7 Synthesis of Compounds 1-66
By the method of the above compound 1-1, compound 1-66 (23.59 g) was synthesized, and the purity of the solid was not less than 98.7% by HPLC. Mass spectrum m/z:906.3498 (theory: 906.3430). Theoretical element content (%) C 67 H 46 N 2 Si: c,88.71; h,5.11; n,3.09 measured element content (%): c,88.73; h,5.16; n,3.07.
EXAMPLE 8 Synthesis of Compounds 1-81
By the method of the above compound 1-1, compound 1-81 (21.23 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:855.3346 (theoretical value: 855.3321 theoretical element content (%) C 64 H 45 NSi: c,89.79; h,5.30; n,1.64 measured element content (%): c,89.75; h,5.34; n,1.63.
EXAMPLE 9 Synthesis of Compounds 1-118
By the method of compound 1-1 described above, compound 1-118 (20.50 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:853.3188 (theory: 853.3165). Theoretical element content (%) C 64 H 43 NSi: c,90.00; h,5.07; n,1.64 measured element content (%): c,90.00; h,5.09; n,1.62.
EXAMPLE 10 Synthesis of Compounds 1-153
By the method of the above compound 1-1, compound 1-153 (19.96 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:817.3793 (theory: 817.3740). Theoretical element content (%) C 59 H 51 NOSi: c,86.62; h,6.28; n,1.71 measured element content (%): c,86.65; h,6.25; n,1.66.
The compound thus obtained by the above example 2-example 10 is as follows:
EXAMPLE 11 Synthesis of Compound 2-1
Step1: synthetic intermediate B-1
Toluene (600 mL), M-1 (12.61 g,0.06 mol), n-1 (23.64 g,0.06 mol), palladium acetate (0.18 g,0.80 mmol), sodium t-butoxide (8.65 g,0.09 mol) and tri-t-butylphosphine (11 mL of a 1.0M toluene solution) were sequentially added to a 1L reaction flask under nitrogen, and reacted at 100℃for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give intermediate B-1 (23.90 g, 76% yield) as a recrystallized solid, which was > 99.5% pure by HPLC.
Step2: synthesis of Compound 2-1
Toluene solvent (600 ml), p-1 (7.91 g,32 mmol), intermediate B-1 (16.77 g,32 mmol) and Pd were added sequentially to a 1L reaction flask under nitrogen 2 (dba) 3 (458 mg,0.5 mmol), BINAP (0.20 g,3.2 mmol) and sodium tert-butoxide (7.68 g,80 mmol) were dissolved by stirring and reacted under reflux for 24 hours under the protection of nitrogen, after the reaction was completed, the reaction solution was washed with dichloromethane and distilled water and extracted by liquid separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, and the organic layer was purified with cyclohexane: ethyl acetate=10:1 is used as an eluent for column chromatography separation, purification and refining, and finally the solid compound 2-1 (19.68 g, yield 80%) is obtained, and the purity of the solid detected by HPLC is not less than 99.8%.
Mass spectrum m/z:690.2385 (theory: 690.2307). Theoretical element content (%) C 50 H 30 N 2 O 2 : c,86.94; h,4.38; n,4.06 actual measurement elementContent (%) of element: c,86.97; h,4.33; n,4.13.
EXAMPLE 12 Synthesis of Compounds 2-4
By the method of compound 2-1 described above, compound 2-4 (17.66 g) was synthesized and the solid purity was ≡ 99.4% by HPLC. Mass spectrum m/z:766.2629 (theory: 766.2620). Theoretical element content (%) C 56 H 34 N 2 O 2 : c,87.71; h,4.47; n,3.65 measured element content (%): c,87.73; h,4.45; n,3.72.
EXAMPLE 13 Synthesis of Compounds 2-33
By the method of compound 2-1 described above, compound 2-33 (16.17 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:664.2172 (theory: 664.2151). Theoretical element content (%) C 48 H 28 N 2 O 2 : c,86.73; h,4.25; n,4.21 measured element content (%): c,86.78; h,4.20; n,4.19.
EXAMPLE 14 Synthesis of Compounds 2-46
By the method of compound 2-1 described above, compound 2-46 (17.87 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:706.2095 (theory: 706.2079). Theoretical element content (%) C 50 H 30 N 2 OS: c,84.96; h,4.28; n,3.96 measured element content (%): c,84.97; h,4.27; n,3.88.
EXAMPLE 15 Synthesis of Compounds 2-77
By the method of compound 2-1 described above, compound 2-77 (18.89 g) was synthesized and the solid purity was ≡ 99.7% by HPLC. Mass spectrum m/z:802.3565 (theory: 802.3559). Theoretical element content (%) C 58 H 46 N 2 O 2 : c,86.75; h,5.77; n,3.49 measured element content (%): c,86.77; h,5.75; n,3.47.
EXAMPLE 16 Synthesis of Compounds 2-81
By the method of compound 2-1 described above, compound 2-81 (19.27 g) was synthesized and the solid purity was ≡ 99.9% by HPLC. Mass spectrum m/z:802.3573 (theory: 802.3559). Theoretical element content (%) C 58 H 46 N 2 O 2 : c,86.75; h,5.77; n,3.49 measured element content (%): c,86.77; h,5.71; n,3.53.
EXAMPLE 17 Synthesis of Compounds 2-87
By the method of compound 2-1 described above, compound 2-87 (21.79 g) was synthesized and the solid purity was. Mass spectrum m/z:883.4199 (theory: 883.4186). Theoretical element content (%) C 64 H 45 D 5 N 2 O 2 : c,86.94; h,6.27; n,3.17 measured element content (%): c,86.96; h,6.33; n,3.11.
EXAMPLE 18 Synthesis of Compounds 2-129
By the method of compound 2-1 described above, compound 2-129 (18.53 g) was synthesized and the solid purity was ≡ 99.6% by HPLC. Mass spectrum m/z:824.3436 (theory: 824.3403). Theoretical element content (%) C 60 H 44 N 2 O 2 : c,87.35; h,5.38; n,3.40 measured element content (%): c,87.33; h,5.35; n,3.43.
EXAMPLE 19 Synthesis of Compounds 2-182
By the method of compound 2-1 described above, compound 2-182 (19.39 g) was synthesized, and the purity of the solid was. Mass spectrum m/z:877.4086 (theory: 877.4032). Theoretical element content (%) C 64 H 51 N 3 O: c,87.54; h,5.85; n,4.79 measured element content (%): c,87.50; h,5.90; n,4.78.
EXAMPLE 20 Synthesis of Compounds 2-199
By the method of compound 2-1 described above, compound 2-199 (20.72 g) was synthesized and the purity of the solid was. Mass spectrum m/z:840.3185 (theory: 840.3141). Theoretical element content (%) C 63 H 40 N 2 O: c,89.97; h,4.79; n,3.33 measured element content (%): c,89.99; h,4.74; n,3.36.
The compound thus obtained by the above example 12-example 20 was as follows:
refractive index (n) is determined by J.A. Woollam, inc., model: m-2000 spectrum ellipsometer measurement, the test is atmospheric environment, the scanning range of the instrument is 245 nm-1000 nm; the glass substrate has a size of 200X 200mm and a material film thickness of 20-60 nm. Refractive index tests were performed on the silicon-containing triarylamine compound and the spirofluorene-containing triarylamine compound of the present invention, respectively, and the results are shown in table 1 below.
TABLE 1 photophysical property test of light emitting device
Comparative example 1 device preparation example:
the organic electroluminescent device is prepared by utilizing a vacuum thermal evaporation method. The experimental steps are as follows: repeatedly washing the ITO-Ag-ITO substrate with a glass cleaner, washing the ITO-Ag-ITO substrate in distilled water for 2 times, ultrasonically washing for 15 minutes, sequentially ultrasonically washing solvents such as isopropanol, acetone, methanol and the like after the distilled water is washed, drying at 120 ℃, and delivering the materials into an evaporator.
A hole injection layer compound HIL/40nm, a hole transport layer HT/40nm, a light emitting layer (host GH-1: GH-2: GD-1 (45%: 10% mixing))/30 nm, then an electron transport layer ET/30nm, an electron injection layer LiF/1nm, a cathode Mg-Ag (Mg: ag doping ratio 9:1)/25 nm, and then a capping layer compound 2-1/50nm were evaporated on the cathode layer, on the ready ITO-Ag-ITO electrode by layer vacuum evaporation.
Application examples 1 to 10
Application example 1: the organic electroluminescent device is prepared by utilizing a vacuum thermal evaporation method. The experimental steps are as follows: repeatedly washing the ITO-Ag-ITO substrate with a glass cleaner, washing the ITO-Ag-ITO substrate in distilled water for 2 times, ultrasonically washing for 15 minutes, sequentially ultrasonically washing solvents such as isopropanol, acetone, methanol and the like after the distilled water is washed, drying at 120 ℃, and delivering the materials into an evaporator.
The hole injection layer compound HIL/40nm, the hole transport layer HT/40nm, the light emitting layer (host GH-1: GH-2: GD-1 (45%: 10% mixing))/30 nm, then the electron transport layer ET/30nm, the electron injection layer LiF/1nm, the cathode Mg-Ag (Mg: ag doping ratio 9:1)/25 nm, then the second capping layer compound 2-1/20nm, the first capping layer compound 1-1/30nm, were evaporated on the prepared ITO-Ag-ITO electrode by layer vacuum evaporation.
Application example 2: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-13 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-4 of the present invention.
Application example 3: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-17 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-33 of the present invention.
Application example 4: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-38 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-46 of the present invention.
Application example 5: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-45 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-77 of the present invention.
Application example 6: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-50 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-81 of the present invention.
Application example 7: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-66 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-87 of the present invention.
Application example 8: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-81 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-129 of the present invention.
Application example 9: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-118 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-182 of the present invention.
Application example 10: the first capping layer compound 1-1 of the organic electroluminescent device was exchanged for compound 1-153 and the second capping layer compound 2-1 of the organic electroluminescent device was exchanged for compound 2-199 of the present invention.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company, U.S. are combined into a combined IVL test system to test the luminous efficiency and CIE color coordinates of the organic electroluminescent device.
The results of the luminescence characteristic test of the obtained organic electroluminescent device are shown in table 1. Table 1 shows the results of the light emitting characteristics test of the light emitting devices prepared with the compounds prepared in the examples of the present invention and the comparative substances.
TABLE 1 test of light emitting characteristics of light emitting device
As can be seen from the results of table 1, the organic electroluminescent device of the present invention can better improve the luminous efficiency of the organic electroluminescent device by selecting a double-layered cover layer composed of two materials having different refractive indexes as compared with comparative example 1.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.
Claims (8)
1. An organic electroluminescent device sequentially comprising an anode electrode, an organic layer, a cathode electrode and a cover layer, wherein the cover layer comprises a first cover layer and a second cover layer, the refractive index of the first cover layer at 450-630 nm is 1.4-1.8, and the refractive index of the second cover layer at 450-630 nm is 1.9-3.0; the first capping layer comprises a silicon-containing triarylamine compound represented by formula I,
wherein A is selected from one of the formulas (1) - (3):
r is selected from one of hydrogen and deuterium identically or differently;
the Ar is as follows a One selected from the following groups:
Wherein R is 12 One selected from phenyl, tolyl, biphenyl and naphthyl;
R p selected from deuterium;
q is 0, 1 or 2;
L c one selected from the following groups:
-is a single bond or none;
L a 、L b selected from single bonds;
R a the hydrogen, deuterium, and substituted or unsubstituted C1-C6 alkyl are selected from the same or different;
R b the hydrogen, deuterium, and substituted or unsubstituted C1-C6 alkyl are selected from the same or different;
r is 0, 1, 2, 3 or 4; a is 0, 1, 2, 3 or 4; b is 0, 1, 2, 3 or 4;
the term "substituted" refers to mono-or poly-substitution with deuterium.
2. The organic electroluminescent device of claim 1, wherein R a And R is b Independently selected from one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl.
3. The organic electroluminescent device according to claim 1, wherein the silicon-containing triarylamine compound represented by formula i is selected from any one of the chemical structures shown below:
4. the organic electroluminescent device according to claim 1, wherein the second cover layer contains a spirofluorene-containing triarylamine compound represented by the following formula ii:
wherein R is 1 、R 2 、R 3 Independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
L 1 、L 2 、L 3 Independently selected from one of single bond, substituted or unsubstituted C6-C25 arylene, and substituted or unsubstituted C2-C20 heteroarylene;
X 1 selected from O, S or NR 0 Wherein R is 0 One selected from the group consisting of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C25 aryl group, and a substituted or unsubstituted C2-C20 heteroaryl group;
R 4 one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl;
x is selected from O, S, NR 00 Or CR (CR) 11 R 11 Wherein R is 00 Selected from substituted or unsubstitutedOne of C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, R 11 The compounds are selected from one of hydrogen, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
R 5 one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl;
m is selected from 0, 1, 2, 3 or 4; n is selected from 0, 1, 2, 3 or 4; p is selected from 0, 1, 2, 3 or 4; q is selected from 0, 1, 2, 3 or 4; o is selected from 0, 1, 2, 3 or 4;
When m is greater than 1, each R 1 Identical or different, adjacent R' s 1 Can form benzene ring; when n is greater than 1, each R 2 Identical or different, adjacent R' s 2 Can form benzene ring; when p is greater than 1, each R 3 Identical or different, adjacent R' s 3 Can form benzene ring; when q is greater than 1, each R 4 Identical or different, adjacent R' s 4 Can form benzene ring or naphthalene ring; when o is greater than 1, each R 5 Identical or different, adjacent R' s 5 Can be benzene ring.
5. The organic electroluminescent device of claim 4, wherein the R 1 、R 2 、R 3 Independently selected from one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, phenyl, pentadeuterated phenyl, tolyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, 9-diphenylfluorenyl, spirofluorenyl;
m is selected from 0, 1 or 2; n is selected from 0, 1 or 2; p is selected from 0, 1 or 2.
6. The organic electroluminescent device of claim 4, wherein the X 1 Selected from O, S or NR 0 Wherein R is 0 Selected from methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, phenyl, methylOne of phenyl, biphenyl and naphthyl; q is selected from 0, 1, 2, 3 or 4;
R 4 One of the following substituents is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl or:
7. the organic electroluminescent device of claim 4, wherein the R 5 One of the following substituents is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, camphene, norbornyl or the like:
x is selected from O, S, NR 00 Or CR (CR) 11 R 11 Wherein R is 00 One selected from phenyl, pentadeuterated phenyl, tolyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl and fluorenyl, R 11 The two groups are selected from one of hydrogen, phenyl, pentadeuterated phenyl, tolyl, biphenyl, terphenyl and naphthyl identically or differently;
o is selected from 0, 1 or 2.
8. The organic electroluminescent device of claim 4, wherein the L 1 、L 2 、L 3 Independently selected from a single bond or any one of the following groups:
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| KR20160066635A (en) * | 2014-12-02 | 2016-06-13 | 엘지디스플레이 주식회사 | Organic light emitting display device |
| CN111933818A (en) * | 2020-08-12 | 2020-11-13 | 长春海谱润斯科技有限公司 | Organic light-emitting device |
| CN111943902A (en) * | 2020-08-21 | 2020-11-17 | 长春海谱润斯科技有限公司 | Triarylamine compound and organic light-emitting device thereof |
| CN112038501A (en) * | 2020-09-08 | 2020-12-04 | 长春海谱润斯科技股份有限公司 | Top-emitting organic electroluminescent device |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160066635A (en) * | 2014-12-02 | 2016-06-13 | 엘지디스플레이 주식회사 | Organic light emitting display device |
| CN111933818A (en) * | 2020-08-12 | 2020-11-13 | 长春海谱润斯科技有限公司 | Organic light-emitting device |
| CN111943902A (en) * | 2020-08-21 | 2020-11-17 | 长春海谱润斯科技有限公司 | Triarylamine compound and organic light-emitting device thereof |
| CN112038501A (en) * | 2020-09-08 | 2020-12-04 | 长春海谱润斯科技股份有限公司 | Top-emitting organic electroluminescent device |
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