WO2022242584A1 - Dispositif électroluminescent organique et appareil d'affichage - Google Patents
Dispositif électroluminescent organique et appareil d'affichage Download PDFInfo
- Publication number
- WO2022242584A1 WO2022242584A1 PCT/CN2022/092948 CN2022092948W WO2022242584A1 WO 2022242584 A1 WO2022242584 A1 WO 2022242584A1 CN 2022092948 W CN2022092948 W CN 2022092948W WO 2022242584 A1 WO2022242584 A1 WO 2022242584A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- emitting layer
- ito
- lif
- dpypa
- Prior art date
Links
- -1 bipyridyl compound Chemical class 0.000 claims abstract description 102
- 239000000463 material Substances 0.000 claims abstract description 73
- 239000010410 layer Substances 0.000 claims description 202
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 239000002346 layers by function Substances 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl 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])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 125000005266 diarylamine group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 abstract description 6
- BVBRZOLXXOIMQG-UHFFFAOYSA-N fluoroborane Chemical compound FB BVBRZOLXXOIMQG-UHFFFAOYSA-N 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 165
- 230000000052 comparative effect Effects 0.000 description 23
- 230000005525 hole transport Effects 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 13
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 239000002356 single layer Substances 0.000 description 6
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 238000010549 co-Evaporation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 230000009191 jumping Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- LECWCFCIHFAJRO-UHFFFAOYSA-N 3-methylidene-2-pyridin-2-yl-4h-pyridine Chemical class C=C1CC=CN=C1C1=CC=CC=N1 LECWCFCIHFAJRO-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 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
- 230000007423 decrease Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000003944 tolyl 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
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Definitions
- the invention relates to an organic electroluminescence device and a display device, belonging to the technical field of organic electroluminescence.
- Organic Light Emitting Diode (Organic Light Emitting Diode, referred to as OLED) is a device that is driven by current to achieve the purpose of emitting light. Its main characteristics come from the organic light-emitting layer. When an appropriate voltage is applied, electrons and holes Excitons are combined in the organic light-emitting layer to emit light of different wavelengths according to the characteristics of the organic light-emitting layer.
- the light-emitting layer is composed of host materials and doped dyes, and the dyes are mostly selected from traditional fluorescent materials and phosphorescent materials. Specifically, traditional fluorescent materials have the disadvantage of not being able to utilize triplet excitons.
- phosphorescent materials can achieve 100% energy use efficiency by introducing heavy metal atoms, such as iridium or platinum, to realize the transition from singlet excitons to triplet states, but Heavy metals such as iridium or platinum are very scarce, expensive and easily cause environmental pollution, so phosphorescent materials cannot be the first choice for dyes.
- Thermally activated delayed fluorescent materials can realize reverse intersystem jumping from triplet excitons to singlet states by absorbing ambient heat, and then emit fluorescence from singlet states.
- the lifetime of triplet excitons in TADF materials is long, and the device efficiency drops Large drop, poor stability and other shortcomings.
- the purpose of the present invention is to provide an organic electroluminescence device, the organic light-emitting layer of the device uses a wide bandgap material as the main material, doped with a boron-nitrogen compound of a specific structure as a luminescent dye, and realizes 100% exciton utilization, thereby improving the efficiency and stability of organic light-emitting devices.
- An organic electroluminescent device comprising a first electrode, a second electrode and an organic functional layer
- the organic functional layer includes an organic light-emitting layer
- the organic light-emitting layer includes a host material and a luminescent dye
- the host material is Wide bandgap material
- the singlet energy level (S 1 h ) of the host material is greater than the singlet energy level (S 1 g ) of the luminescent dye
- the triplet energy level (T 1 h ) of the host material is greater than or equal to the second triplet energy level (T 2 g ) of the luminescent dye
- the second triplet energy level (T 2 g ) of the luminescent dye is greater than or equal to the first singlet energy level (S 1 g )
- the luminescent dye is a fluoroborazine methylene bipyridine compound or a fluoroboron methylene bipyridine compound.
- the doping ratio of the fluoroborazine methylene bipyridine compound or the fluoroboron methylene bipyridine compound in the organic light-emitting layer as a luminescent dye is 0.1-50wt%; the proportion of the wide bandgap material as the host material in the organic light-emitting layer is 50-99.9wt%.
- fluoroborazine methylene bipyridine compound or fluoroboromethylene bipyridine compound used as a luminescent dye has a structure shown in the following formula [1]:
- Y is C or N
- Ring A and ring A' are respectively independently represented as azine rings, and the number of carbon atoms in the azine rings is 4-12;
- R 1 and R 2 are independently represented as halogen
- R 3 and R 4 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C36 chain alkyl, substituted or unsubstituted C3-C36 cycloalkyl, C1-C10 alkoxy, cyanide C6-C30 arylamino group, C3-C30 heteroarylamino group, substituted or unsubstituted C6-C60 monocyclic aryl group, C6-C60 fused-ring aryl group, C6-C60 aryloxy group, C5 - one of C60 monocyclic heteroaryl, C5-C60 condensed ring heteroaryl, trimethylsilyl, said R 3 and R 4 are independently connected to the connected azine ring to form a ring or Not connected into a ring;
- n are each independently selected from 1 to the maximum allowed integer value
- the substituents are selected from deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, cyano, C6-C30 Arylamino, C3 ⁇ C30 heteroarylamino, C6 ⁇ C60 monocyclic aryl, C6 ⁇ C60 condensed ring aryl, C6 ⁇ C60 aryloxy, C5 ⁇ C60 monocyclic heteroaryl, C5 One or a combination of at least two of ⁇ C60 fused-ring heteroaryl groups.
- fluoroborazine methylene bipyridine compound or the fluoroboromethylene bipyridine compound used as a luminescent dye has a structure as shown in formula [2]:
- X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently selected from a carbon atom or a nitrogen atom;
- n and n are independently selected from 2 to 4 integers;
- Y, R 1 , R 2 are the same as those defined in formula [1]
- the definitions of R 3 and R 4 are the same as those defined in formula [1]
- at least one R 3 can be phenyl and Ring B is fused and connected, and there may be at least one R 4 that is phenyl and is fused and connected with ring B'.
- X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently selected from carbon atoms;
- R 1 and R 2 are both fluorine atoms
- one R3 is phenyl and is fused to ring B
- one R4 is phenyl and is fused to ring B' .
- the fluoroborazine methylene bipyridine compound as a luminescent dye has a structure as shown in any one of formula (1), formula (2), formula (3) or formula (4):
- the fluoroboromethylene bipyridine compound as a luminescent dye has a structure as shown in any one of formula (5), formula (6), formula (7) or formula (8):
- formula (2), formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), R 3 , R 4 Each independently selected from hydrogen, deuterium or one of the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2 -Methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethyl Hexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthy
- the fluoroborazine methylene bipyridine compound or the fluoroboromethylene bipyridine compound used as a luminescent dye is selected from any of the formulas (F-1)-(F-400) Compound:
- the host material in the light-emitting layer it is selected from carbazole derivatives, carboline derivatives, spirofluorene derivatives, fluorene derivatives, silicon-containing derivatives, phosphine-containing derivatives , at least one compound in derivatives containing sulfone groups;
- the wide bandgap material is preferably selected from but not limited to compounds shown in any of the following structures:
- the present invention also provides the application of the above-mentioned organic electroluminescent device of the present invention, and the application is an application in an organic electronic device, and the organic electronic device includes an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field Effect transistors, organic thin-film solar cells, information labels, electronic artificial skin sheets, sheet-type scanners or electronic paper.
- the present invention also protects a display device including the above-mentioned organic electroluminescent device of the present invention, and the display device includes but not limited to display elements, lighting elements, information labels, electronic artificial skin sheets or electronic paper.
- Fig. 1 is a diagram of the light emitting mechanism of the organic electroluminescent device of the present invention.
- Fig. 2 is a schematic structural view of an organic electroluminescent device prepared in an example of the present invention.
- the light emitting mechanism of the organic electroluminescent device of the present invention is as follows:
- the second triplet energy level (T 2 ) of this type of dye is quite different from the first triplet energy level (T 1 ), so the radiative transition rate (k p T2 ) from T 2 to S 0 is greater than that from T 2 to S 0
- the internal conversion rate (k IC ) of T 1 that is, the triplet state of this kind of dye has the phenomenon of anti-Kasha rule.
- the T 2 energy level of this type of dye is close to the S 1 energy level, and there is a reverse intersystem jumping process from T 2 to S 1. Therefore, singlet and triplet excitons are generated when holes and electrons recombine. All types of dyes can be utilized.
- the above-mentioned dye is matched with a wide-bandgap host, so that the dye concentration can be diluted, and the triplet-triplet annihilation (TTA) and triplet-polaron annihilation (TPA) are reduced.
- TTA triplet-triplet annihilation
- TPA triplet-polaron annihilation
- the exciton utilization rate of the dye is further improved, and the stability of the device is enhanced.
- the boron compound-doped dye with a specific structure used in the present invention does not have obvious intramolecular charge transfer, so it is beneficial to the narrowing of the spectrum and improves the color purity of the device.
- the organic electroluminescent device of the present invention includes an anode 2 , a hole transport region 3 , an organic light-emitting layer 4 , an electron transport region 5 and a cathode 6 sequentially deposited on a substrate 1 .
- the substrate can be made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency.
- a thin-film transistor (TFT) may be provided on a substrate for a display.
- the anode can be formed by sputtering or depositing the anode material on the substrate, wherein the anode material can be indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and other oxide transparent conductive materials and any combination thereof;
- the cathode can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg- In), magnesium-silver (Mg-Ag) and other metals or alloys and any combination thereof.
- the organic material layer of the hole transport region, the light-emitting layer, the electron transport region and the cathode can be sequentially prepared on the anode by vacuum thermal evaporation, spin coating, printing and other methods.
- the compound used as the organic material layer may be small organic molecules, organic macromolecules, polymers, and combinations thereof.
- the present invention innovates the composition of the organic light-emitting layer, specifically, the organic light-emitting layer of the present invention includes a host material and a fluoroborazamethylene bipyridine compound or a fluoroboromethylene bipyridine compound as a luminescent dye .
- the host material is a wide bandgap material, the singlet energy level (S 1 h ) of the wide bandgap material is greater than that of the doped dye (S 1 g ), and the triplet energy level (T 1 h ) of the wide bandgap material greater than the second triplet energy level (T 2 g ) of the dopant dye; the second triplet energy level (T 2 g ) of the luminescent dye is greater than the first singlet energy level (S 1 g ) of the luminescent dye.
- the host material of the present invention is a wide bandgap material, which can dilute the concentration of fluoroborazine methylene bipyridine compounds or fluoroboron methylene bipyridine compounds as luminescent dyes, effectively reducing the exciton density , so as to effectively suppress triplet-triplet annihilation (TTA) and exciton-polaron quenching (TPA), further enhance the stability of organic electroluminescent devices, improve device life, and reduce efficiency roll-off.
- TTA triplet-triplet annihilation
- TPA exciton-polaron quenching
- the difference between the HOMO energy level and the LUMO energy level of the wide bandgap material of the present invention is greater than or equal to 2eV, thereby ensuring that the singlet state and triplet state of the wide bandgap material are at a higher energy level, which is beneficial to the wide bandgap material to the luminescent dye of the present invention.
- the fluoroborazine methylene bipyridine compound or the fluoroboron methylene bipyridine compound used as a luminescent dye in the present invention has a planar aromatic rigid structure and a stable structure. Its second triplet energy level (T 2 ) is quite different from the first triplet energy level (T 1 ), so the radiative transition rate (k p T2 ) from T 2 to S 0 is greater than that from T 2 to T 1
- the internal conversion rate (k IC ) that is, the triplet state of such dyes has the phenomenon of anti-Kasha rule.
- the T 2 energy level of this type of dye is close to the S 1 energy level, and there is a reverse intersystem crossing process from T 2 to S 1. Therefore, singlet and triplet excitons are generated when holes and electrons recombine. All types of dyes can be utilized.
- the first singlet energy level of the host material wide bandgap material is greater than the first singlet energy level of the boron compound dye, and the first singlet energy level of the host material wide bandgap material is greater than the second singlet energy level of the luminescent dye.
- the first triplet energy level of the host material wide bandgap material is greater than the second triplet energy level of the luminescent dye, therefore, after the organic electroluminescent device is electrically excited, the singlet energy level of the wide bandgap host
- Both the heavy state and the triplet excitonic energy can be transferred to the singlet state and triplet state of the dye material respectively; or the holes and electrons are directly recombined on the dye, which is realized through the reverse intersystem crossing process of the dye T 2 to S 1 High-efficiency light emission, and finally the singlet and triplet energy in the organic electroluminescent device has been fully utilized, which improves the luminous efficiency of the organic electroluminescent device; therefore, the present invention can effectively reduce the concentration of triplet excitons, thereby solving the problem of The problem of serious roll-off decline under high brightness effectively enhances the stability of the organic electroluminescent device.
- the first triplet energy level (T 1 h ) of the host material wide bandgap material is at least 0.1eV higher than the second triplet energy level (T 2 g ) of the luminescent dye, that is, T 1 h -T 2 g >0.1eV;
- the first singlet energy level (S 1 g ) of the luminescent dye is at least 0.3eV higher than the first triplet energy level (T 1 g ), that is, S 1 g -T 1 g >0.3eV;
- the second triplet energy level (T 2 g ) of the compound dye is at least 0.3eV higher than the first triplet energy level (T 1 g ), ie T 2 g -T 1 g >0.3eV;
- the present invention innovates the composition of the organic light-emitting layer, and uses a wide-bandgap host to match such a fluoroborazamethylene bipyridine compound or a fluoroboromethylene bipyridine compound as a luminescent dye, which can not only improve the organic light emission
- a fluoroborazamethylene bipyridine compound or a fluoroboromethylene bipyridine compound as a luminescent dye
- the proportion of the wide bandgap material in the organic light-emitting layer is 50wt%-99.9wt%; the proportion of the luminescent dye in the organic light-emitting layer is 0.1wt%-50wt%.
- the stability of the device is higher and the lifetime is gradually extended.
- An organic electroluminescent device includes an anode, a cathode, and a layer of organic material between the two electrodes.
- the organic material can be divided into multiple regions.
- the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.
- the material of the anode can be oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof.
- the cathode material can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag ) and other metals or alloys and any combination of them.
- the hole transport region is located between the anode and the light emitting layer.
- the hole transport region can be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole-transport layer containing only one compound and a single-layer hole-transport layer containing multiple compounds.
- the hole transport region may also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).
- HIL hole injection layer
- HTL hole transport layer
- EBL electron blocking layer
- the material of the hole transport region can be selected from but not limited to phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4 - Styrene sulfonate) (Pani/PSS), aromatic amine derivatives, etc.
- phthalocyanine derivatives such as CuPc
- conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-
- the luminescent layer includes luminescent dyes (that is, dopant) that can emit different wavelength spectra, and can also include a host material (Host) at the same time.
- the light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, or blue.
- a plurality of monochromatic light-emitting layers of different colors can be arranged planarly according to the pixel pattern, and can also be stacked together to form a colored light-emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other.
- the light-emitting layer can also be a single color light-emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
- the electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron-transport layer containing only one compound and a single-layer electron-transport layer containing multiple compounds.
- the electron transport region may also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
- EIL electron injection layer
- ETL electron transport layer
- HBL hole blocking layer
- the present invention also provides a preparation method of the organic electroluminescent device, which is illustrated by taking FIG. 1 as an example, including sequentially depositing an anode 2, a hole transport region 3, an organic light-emitting layer 4, an electron transport region 5, and a cathode 6 on a substrate 1, Then package.
- the organic light-emitting layer 4 is formed by co-evaporating a wide bandgap material source, an electron donor material source, an electron acceptor material source and a resonant TADF material source.
- the preparation method of the organic electroluminescent device of the present invention comprises the following steps:
- the light-emitting layer includes the host material and TADF dye.
- the evaporation rate of the host material and the evaporation rate of the sensitizer material are adjusted by the method of multi-source co-evaporation. and the evaporation rate of the dye to make the dye reach the preset doping ratio;
- the electron transport layer material of the device is vacuum evaporated on the organic light-emitting layer, and the evaporation rate is 0.1-0.5nm/s;
- An embodiment of the present invention also provides a display device, which includes the organic electroluminescent device as provided above.
- the display device may be a display device such as an OLED display, and any product or component having a display function such as a TV, a digital camera, a mobile phone, a tablet computer, etc. including the display device.
- the display device has the same advantages as that of the above-mentioned organic electroluminescent device over the prior art, which will not be repeated here.
- the organic electroluminescence device of the present invention will be further introduced through specific examples below.
- the OLED includes sequentially stacked anode/hole injection layer/hole transport layer/first exciton blocking layer/light emitting layer/second exciton blocking layer/electron transport layer/electron injection layer /cathode.
- the anode is ITO; the hole injection layer is HATCN; the hole transport layer is NPB; the electron transport layer is DPyPA and Liq co-evaporation; the electron injection layer is LiF; the cathode is Al.
- the glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent, baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light. Light and ozone cleaning, and bombardment of the surface with a beam of low-energy cations;
- HATCN was vacuum evaporated on the ITO transparent conductive layer as the hole injection layer of the device, the evaporation rate was 0.1nm/s, and the total film thickness was 5nm;
- NPB hole transport layer of the device
- the evaporation rate was 0.1nm/s
- the total film thickness was 30nm
- the light-emitting layer of the device is vacuum-evaporated on the hole-transporting layer, and the light-emitting layer of the present invention includes a host material and a dye material. Adjust the evaporation rate of the main material to 0.1nm/s, adjust the evaporation rate of the dye in the luminescent layer to be 1% of the evaporation rate of the main body, and set the total film thickness of the luminescent layer to 30nm;
- the co-evaporation ratio is 1:1, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
- LiF with a thickness of 0.5 nm was vacuum evaporated on the electron transport layer as the electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.
- the first triplet energy level of the host material, the first singlet state and the second triplet energy level of the boron compound dye are shown in Table 1.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the device structure of this comparison example is as follows:
- the meaning of the device of this comparative example is roughly the same as that of Example 1, the only difference is that the main body of the organic light-emitting layer and the type of dye are different.
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the organic electroluminescent device (embodiment 1-100, comparative example 1-10) prepared by the above-mentioned process is subjected to following performance measurement: the characteristics such as the current, voltage, luminance, luminescence spectrum, current efficiency, external quantum efficiency of the prepared device Adopt PR 655 spectral scanning luminance meter and Keithley K2400 digital source meter system to test synchronously.
- Turn-on voltage increase the voltage at a rate of 0.1V per second, and measure the voltage when the brightness of the organic electroluminescent device reaches 1cd/m2, which is the turn - on voltage;
- this type of organic electroluminescent device of the present invention adopts a brand-new combination scheme of host materials and dyes, and the devices prepared thereby have excellent photoelectric properties, and the electroluminescence external quantum efficiencies of all devices All are above 12%, showing overall superiority.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
L'invention concerne un dispositif électroluminescent organique et un appareil d'affichage, se rapportant au domaine technique de l'électroluminescence organique. Le dispositif électroluminescent organique selon la présente invention comprend une couche électroluminescente organique (4). La couche électroluminescente organique (4) comprend un matériau hôte et un colorant électroluminescent ; le matériau hôte est un matériau à large bande interdite, le niveau d'énergie de singulet du matériau hôte est supérieur au premier niveau d'énergie de singulet du colorant électroluminescent, et le niveau d'énergie de triplet du matériau hôte est supérieur ou égal au second niveau d'énergie de triplet du colorant électroluminescent ; et le second niveau d'énergie de triplet du colorant électroluminescent est supérieur ou égal au premier niveau d'énergie de singulet du colorant électroluminescent ; et le colorant électroluminescent est un composé bipyridyle d'azaméthylène fluoroboré ou un composé bipyridyle de méthylène fluoroboré. Le dispositif selon la présente invention atteint 100 % d'utilisation d'excitons par régulation d'une relation de niveau d'énergie sujet-objet, ce qui permet d'améliorer l'efficacité et la stabilité du dispositif électroluminescent organique.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022564365A JP2023529546A (ja) | 2021-05-17 | 2022-05-16 | 有機電界発光デバイスおよび表示装置 |
| KR1020227036685A KR20220156916A (ko) | 2021-05-17 | 2022-05-16 | 유기 전계 발광 소자 및 디스플레이 장치 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110534029.8 | 2021-05-17 | ||
| CN202110534029.8A CN113437229B (zh) | 2021-05-17 | 2021-05-17 | 一种有机电致发光器件和显示装置 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2022242584A1 true WO2022242584A1 (fr) | 2022-11-24 |
Family
ID=77802669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2022/092948 WO2022242584A1 (fr) | 2021-05-17 | 2022-05-16 | Dispositif électroluminescent organique et appareil d'affichage |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2023529546A (fr) |
| KR (1) | KR20220156916A (fr) |
| CN (1) | CN113437229B (fr) |
| WO (1) | WO2022242584A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113437229B (zh) * | 2021-05-17 | 2022-04-01 | 清华大学 | 一种有机电致发光器件和显示装置 |
| WO2023179986A1 (fr) * | 2022-03-24 | 2023-09-28 | Sony Group Corporation | Colorants à base d'aza-bore-diquinométhène utilisés comme matériau photoactif pour couches de conversion photoélectrique organiques dans des photodiodes organiques |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200523339A (en) * | 2003-12-11 | 2005-07-16 | Eastman Kodak Co | Synthesis of bis(azinyl)amine-bf2 complex |
| CN103183697A (zh) * | 2013-02-26 | 2013-07-03 | 南京大学 | 基于二联杂环并吡咯基团的近红外氟硼二吡咯化合物及其制法和用途 |
| CN107507921A (zh) * | 2017-09-29 | 2017-12-22 | 江苏三月光电科技有限公司 | 一种含硼有机电致发光器件及其制备方法 |
| CN109346614A (zh) * | 2018-08-31 | 2019-02-15 | 昆山国显光电有限公司 | 一种有机电致发光器件和显示装置 |
| CN113437229A (zh) * | 2021-05-17 | 2021-09-24 | 清华大学 | 一种有机电致发光器件和显示装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1951155A (zh) * | 2004-05-14 | 2007-04-18 | 出光兴产株式会社 | 有机电致发光器件 |
| CN110729408B (zh) * | 2019-10-23 | 2021-09-28 | 昆山国显光电有限公司 | 一种有机电致发光器件和显示装置 |
-
2021
- 2021-05-17 CN CN202110534029.8A patent/CN113437229B/zh active Active
-
2022
- 2022-05-16 KR KR1020227036685A patent/KR20220156916A/ko unknown
- 2022-05-16 WO PCT/CN2022/092948 patent/WO2022242584A1/fr active Application Filing
- 2022-05-16 JP JP2022564365A patent/JP2023529546A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200523339A (en) * | 2003-12-11 | 2005-07-16 | Eastman Kodak Co | Synthesis of bis(azinyl)amine-bf2 complex |
| CN103183697A (zh) * | 2013-02-26 | 2013-07-03 | 南京大学 | 基于二联杂环并吡咯基团的近红外氟硼二吡咯化合物及其制法和用途 |
| CN107507921A (zh) * | 2017-09-29 | 2017-12-22 | 江苏三月光电科技有限公司 | 一种含硼有机电致发光器件及其制备方法 |
| CN109346614A (zh) * | 2018-08-31 | 2019-02-15 | 昆山国显光电有限公司 | 一种有机电致发光器件和显示装置 |
| CN113437229A (zh) * | 2021-05-17 | 2021-09-24 | 清华大学 | 一种有机电致发光器件和显示装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113437229B (zh) | 2022-04-01 |
| CN113437229A (zh) | 2021-09-24 |
| KR20220156916A (ko) | 2022-11-28 |
| JP2023529546A (ja) | 2023-07-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2022257817A1 (fr) | Dispositif électroluminescent organique et appareil d'affichage | |
| CN110407859B (zh) | 一种发光材料及其应用以及包含其的有机电致发光器件 | |
| CN110317139B (zh) | 一种化合物及其应用以及包含该化合物的有机电致发光器件 | |
| CN111333671B (zh) | 一种发光材料及其应用以及包含其的有机电致发光器件 | |
| CN110872316B (zh) | 一种新型化合物及其应用及采用该化合物的有机电致发光器件 | |
| CN111153919B (zh) | 一种发光材料及其应用以及包含其的有机电致发光器件 | |
| CN112174992B (zh) | 一种发光材料及其应用以及包含其的有机电致发光器件 | |
| WO2020042607A1 (fr) | Dispositif électroluminescent organique, son procédé de préparation et dispositif d'affichage associé | |
| WO2022237668A1 (fr) | Composé cyclique fusionné, son utilisation, et dispositif électroluminescent organique le contenant | |
| JP7429055B2 (ja) | 新規化合物及びその応用、並びにこの化合物を使用する有機エレクトロルミネッセンスデバイス | |
| WO2022242584A1 (fr) | Dispositif électroluminescent organique et appareil d'affichage | |
| CN111320612A (zh) | 化合物及有机电致发光器件 | |
| WO2023284103A1 (fr) | Composé organique et son application | |
| CN111943829B (zh) | 一种激基复合物及其应用及采用该激基复合物的有机电致发光器件 | |
| CN111808082A (zh) | 一种发光材料及其应用 | |
| WO2023125276A1 (fr) | Composé organique et son utilisation | |
| CN112142605A (zh) | 一种化合物及其应用、包含其的有机电致发光器件 | |
| CN115197252A (zh) | 一种有机化合物及其应用 | |
| WO2023273998A1 (fr) | Composé et son utilisation, et dispositif électroluminescent organique | |
| CN115043863A (zh) | 一种有机半导体发光化合物及其应用 | |
| CN111153810B (zh) | 一种化合物及其应用、包含该化合物的有机电致发光器件 | |
| CN114478267A (zh) | 用于发光器件的有机化合物及有机电致发光器件 | |
| CN113444090A (zh) | 一种化合物及其应用 | |
| CN116615038A (zh) | 一种有机电致发光器件和显示装置 | |
| CN112661760A (zh) | 用于有机电子材料的化合物及含有其的有机电致发光器件 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENP | Entry into the national phase |
Ref document number: 20227036685 Country of ref document: KR Kind code of ref document: A |
|
| ENP | Entry into the national phase |
Ref document number: 2022564365 Country of ref document: JP Kind code of ref document: A |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22803906 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 22803906 Country of ref document: EP Kind code of ref document: A1 |