CN116615038A - Organic electroluminescent device and display device - Google Patents
Organic electroluminescent device and display device Download PDFInfo
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- CN116615038A CN116615038A CN202310534767.1A CN202310534767A CN116615038A CN 116615038 A CN116615038 A CN 116615038A CN 202310534767 A CN202310534767 A CN 202310534767A CN 116615038 A CN116615038 A CN 116615038A
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- 239000000463 material Substances 0.000 claims abstract description 81
- 238000001228 spectrum Methods 0.000 claims abstract description 45
- -1 nitro, cyano, amino Chemical group 0.000 claims description 269
- 150000001875 compounds Chemical class 0.000 claims description 73
- 239000010410 layer Substances 0.000 claims description 70
- 125000001424 substituent group Chemical group 0.000 claims description 46
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 34
- 229910052805 deuterium Inorganic materials 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000001769 aryl amino group Chemical group 0.000 claims description 24
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 21
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 19
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 18
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 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 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 10
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 10
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 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 10
- 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 10
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 10
- 125000001725 pyrenyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 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 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 9
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 238000000295 emission spectrum Methods 0.000 claims description 9
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 9
- 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 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
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- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 8
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 8
- 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 8
- 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 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 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 7
- 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 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 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 7
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 7
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 6
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 6
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 6
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 238000002189 fluorescence spectrum Methods 0.000 claims description 6
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 6
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 6
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 6
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 6
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 5
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 5
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005577 anthracene group Chemical group 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012964 benzotriazole Substances 0.000 claims description 4
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 4
- 125000003748 selenium group Chemical group *[Se]* 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
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- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
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- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 claims 1
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- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 230000007547 defect Effects 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
- 239000011777 magnesium Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 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
- FWXNJWAXBVMBGL-UHFFFAOYSA-N 9-n,9-n,10-n,10-n-tetrakis(4-methylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C2C=CC=CC2=1)C1=CC=C(C)C=C1 FWXNJWAXBVMBGL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 1
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000005465 channeling Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001748 luminescence spectrum 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DCVOWNNIQFCMDW-UHFFFAOYSA-N methoxysilicon Chemical compound CO[Si] DCVOWNNIQFCMDW-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005582 pentacene group Chemical group 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
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
- H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/20—Delayed fluorescence emission
- H10K2101/25—Delayed fluorescence emission using exciplex
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/27—Combination of fluorescent and phosphorescent emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an organic electroluminescent device and a display device, belonging to the technical field of organic electroluminescence. The organic electroluminescent device comprises an organic luminescent layer, wherein the organic luminescent layer comprises a first main body material, a second main body material, a phosphorescent sensitizer and a resonance type narrow spectrum fluorescent material, the first main body material and the second main body material can form an exciplex, the resonance type narrow spectrum fluorescent material has a narrow spectrum emission characteristic, and the Stokes shift of the resonance type narrow spectrum fluorescent material meets the following conditions: lambda is less than or equal to 60nm, and half-peak width meets the following conditions: FWHM is less than or equal to 60nm. The invention can realize 100% exciton utilization rate of the device, and the prepared electroluminescent device has the characteristics of high efficiency and long service life.
Description
Technical Field
The invention relates to an organic electroluminescent device and a display device, which are provided with the organic electroluminescent device which adopts phosphorescent material sensitization as luminescent dye and thermally activates delayed fluorescence, and belongs to the technical field of organic electroluminescence.
Background
An organic electroluminescent diode (Organic Light Emitting Diode, abbreviated as OLED) is a device that emits light by current driving, and has a main characteristic from an organic light emitting layer thereof, in which electrons and holes are combined to generate excitons and emit light of different wavelengths according to the characteristics of the organic light emitting layer when a proper voltage is applied. In the present stage, the light-emitting layer is composed of a host material and a doped dye, and the dye is mostly selected from the traditional fluorescent material and phosphorescent material. Or a thermally activated delayed fluorescence (Thermally Activated Delayed Fluorescence, abbreviated as TADF) material.
In particular, the conventional fluorescent material has a defect that triplet excitons cannot be utilized, and the phosphorescent material can achieve 100% energy use efficiency by introducing heavy metal atoms such as iridium or platinum to realize transition from the singlet excitons to the triplet state, but the heavy metals such as iridium or platinum are very rare, expensive and extremely easy to cause environmental pollution, so the phosphorescent material cannot be the first choice of dye.
Thermally activated delayed fluorescence (Thermally Activated Delayed Fluorescence, abbreviated as TADF) material. Compared with phosphorescent materials and traditional fluorescent materials, the TADF material can realize the reverse intersystem jump of triplet excitons to singlet states through absorbing environmental heat, and further emit fluorescence from the singlet states, so that 100% utilization of the excitons is realized, and no heavy metal is needed. Thus, 100% energy use efficiency is currently achieved primarily by doping the bulk material with TADF material. Transition to singlet state and singlet excitons are able to return to the ground state to fluoresce, thus achieving 100% utilization of excitons without resorting to any heavy metals. At present, higher luminous efficiency is realized mainly by doping a main body material with a TADF material. However, most TADF materials have certain defects, such as too wide light emission spectrum, large roll-off of devices, short lifetime, and the like.
Disclosure of Invention
In order to solve the technical problems, the invention provides an organic electroluminescent device, comprising a substrate, a first electrode, a second electrode and an organic functional layer, wherein the organic functional layer comprises an organic luminescent layer, the organic luminescent layer comprises a main body material, a phosphorescence sensitizer and a resonance type narrow spectrum fluorescent material used as luminescent dye, and the organic electroluminescent device is characterized in that:
the host material is composed of a first host compound and a second host compound, and the first host compound and the second host compound form an exciplex;
the resonance type narrow spectrum fluorescent material is a material with narrow band spectrum emission characteristics, and Stokes displacement of the resonance type narrow spectrum fluorescent material meets the following conditions: lambda is less than or equal to 60nm, and half-peak width meets the following conditions: FWHM is less than or equal to 60nm;
the resonance type narrow spectrum fluorescent material is a compound with a core structure adopting a resonance molecular structure formed by boron atoms and nitrogen atoms, or a compound with a core structure adopting a resonance molecular structure formed by boron atoms, oxygen, sulfur and selenium atoms, or a compound with a core structure adopting a resonance molecular structure formed by carbonyl groups and nitrogen atoms, or a compound with a core structure adopting a resonance molecular structure formed by carbonyl groups, oxygen, sulfur and selenium atoms, or a compound with a core structure adopting an indolocarbazole resonance molecular structure, and the singlet energy level S1 and the triplet energy level T1 of the resonance type narrow spectrum fluorescent material satisfy the formula:
ΔEst＝S1-T1≤0.4eV；
The singlet energy level and the triplet energy level of the second host compound are higher than those of the phosphorescent sensitizer, and the singlet energy level and the triplet energy level of an exciplex formed by the first host compound and the second host compound are also higher than those of the phosphorescent sensitizer;
the triplet state energy level of the exciplex is higher than that of the resonance type narrow spectrum fluorescent material;
the triplet state energy level of the phosphorescence sensitizer is higher than that of the resonance type narrow spectrum fluorescent material.
In the organic electroluminescent device, under the electro-excitation, the singlet excitons of the first host compound and the second host compound forming the exciplex transfer energy to the phosphorescent sensitizer through Forrest energy transfer, and the triplet excitons of the first host compound and the second host compound forming the exciplex transfer energy to the phosphorescent sensitizer through reverse gap channeling to form the singlet excitons and then through Forrest energy transfer, or directly transfer energy to the phosphorescent sensitizer through Dexter energy transfer.
Compared with the traditional host-guest matching mode, the organic electroluminescent device can effectively balance carriers in the device, reduce exciton quenching effect and improve carrier recombination rate of the device; meanwhile, the exciplex formed by the first main body compound and the second main body compound can effectively reduce driving voltage and improve device efficiency and working stability. On the other hand, the multiple energy transfer paths present in the system of the present invention can reduce long-life exciton accumulation, thereby suppressing energy loss and stability degradation caused by the annihilation process of excitons. As shown in fig. 1 of the specification, it is particularly important in the energy transfer diagram that the triplet Dexter Energy Transfer (DET) of the exciplex and the phosphorescent material is particularly important, especially in the case that the excitation in the device generates a high proportion of initial triplet state, because it can effectively convert the TADF triplet state with long service life into the phosphorescent triplet state exciton with shorter service life, and transfer the phosphorescent triplet state exciton to the narrow spectrum dye, so that the prepared electroluminescent device has the characteristics of high efficiency, high color purity and long service life under high brightness.
Further, in the organic electroluminescent device of the present invention, the first host compound is a hole-transporting host having the highest occupied track E HOMO P And the lowest unoccupied track E LUMO P Having a first singlet energy level S 1 P And a first triplet energy level T 1 P (calculated from the Oset values of the fluorescence emission spectrum and the phosphorescence emission spectrum at 77K);
the second host compoundIs an electron transport body with a highest occupied track E HOMO N And the lowest unoccupied track E LUMO N Having a first singlet energy level S 1 N And a first triplet energy level T 1 N (calculated from the Oset values of the fluorescence emission spectrum and the phosphorescence emission spectrum at 77K);
the exciplex formed by the first host compound and the second host compound has a first singlet energy level S 1 EX And a first triplet energy level T 1 EX (calculated from the set values of the fluorescence emission spectrum and the phosphorescence emission spectrum at 77K), the first host compound, the second host compound and the formed exciplex satisfy the following equation:
S 1 EX ━T 1 EX ≤0.3Ev；
E HOMO P ＞E HOMO N ；
E LUMO P ＞E LUMO N ；
E HOMO P －E HOMO N ＞0.2eV；
E LUMO P －E LUMO N ＞0.3eV；
S 1 P ＞S 1 N ≧S 1 EX 。
further, in the organic electroluminescent device of the present invention, the phosphorescent sensitizer has a first singlet energy level S 1 Phos And a first triplet energy level T 1 Phos (S 1 Phos Calculated according to Oset value of tail absorption in the longest wavelength direction of ultraviolet visible absorption spectrum, T 1 Phos Calculated from the Onset value of the phosphorescence emission spectrum at 77K), the following equation is satisfied:
S 1 EX ＞S 1 Phos
T 1 EX ＞T 1 Phos 。
further, in the organic electroluminescent device of the present invention, the first host compound is selected from the group consisting of compounds represented by the following formula 1-1:
in the formula (1-1), the Ar 4 One selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R 001 and R is 002 A substituent group representing a single substitution up to the allowable number, R 001 And R is 002 Each independently selected from one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; and R is 001 、R 002 Are not connected or are connected into a ring between two adjacent to each other;
when substituents are present on the above groups, the substituents are each independently selected from any one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryloxy, C6-C60 aryl, C5-C60 heteroaryl.
Further, in the organic electroluminescent device according to the present invention, the first host compound has a structure as described by formula (1-2) or formula (1-3):
in the formula (1-2) and the formula (1-3), m and n are each independently integers of 1-4;
the Ar is as follows 4 、R 001 And R is 002 Is the same as that in formula (1-1);
the Ar is as follows 5 One selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
the L is selected from one of single bond, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R 003 、R 004 a substituent group representing a single substitution up to the allowable number, R 001 And R is 002 Each independently selected from one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
when substituents are present on the above groups, the substituents are each independently selected from any one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryloxy, C6-C60 aryl, C5-C60 heteroaryl;
Preferably, the Ar 4 、Ar 5 Each independently selected from one or more of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted indole, substituted or unsubstituted indolocarbazole, substituted or unsubstituted carbazole, substituted or unsubstituted fluorene; when Ar is 4 、Ar 5 When a substituent is present on the aromatic hydrocarbon, the substituent is independently selected from any one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl and C5-C30 heteroaryl.
Further, in the organic electroluminescent device of the present invention, the second host compound is a nitrogen-containing aromatic heterocyclic compound having a structure as shown in formula (2-1):
in the formula (2-1), the Q 1 ～Q 5 Independently selected from nitrogen or CR 011 ，R 011 Independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl silicon base, substituted or unsubstituted C6-C30 aryl amino, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; adjacent R 011 Are not connected or are connected and condensed to form a ring;
when R is as above 011 When a substituent is present on the aromatic hydrocarbon, the substituent groups are respectively and independently selected from any one of deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryloxy of C6-C60, aryl of C6-C60 and heteroaryl of C5-C60;
preferably, the Q 1 ～Q 5 One or both of which are nitrogen; more preferably, the Q 1 ～Q 5 Two of which are nitrogen;
preferably, said R 011 Independently selected from the group consisting of hydrogen, deuterium, 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-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthryl, pyrenyl, hole-yl, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, trimericPhenyl, tetrabenzoyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl benzooxazolyl, naphthazolyl, anthracenyl, oxazolyl, phenanthrazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetrazolyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-diazolyl, 1,2, 3-diazolyl, 1,2, 3-diazolyl, 1, 3-diazolyl 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylacridyl, halobenzene, cyanobenzene, trifluoromethyl benzene;
More preferably, said R 011 Independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, phenyl, halobenzene, cyanobenzene, trifluoromethylbenzonaphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthryl, pyrenyl, grottoOne or a combination of two of a group, a perylene group, a fluoranthenyl group, a tetracene group, a pentacene group, a benzopyrene group, a biphenyl group, a terphenyl group, a trimeric phenyl group, a tetrabiphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthrenyl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis-or trans-indenofluorenyl group, a trimeric indenyl group, a spirotrimeric indenyl group, a spiroheterotrimentyl group, a furanyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an isoindolyl group, a carbazolyl group, an indenocarbazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, an acridinyl group, a phenanthridinyl group, a benzo-5, 6-quinolinyl group, a benzo-6, 7-quinolinyl group, and a benzo-7, 8-quinolinyl group.
Further, in the organic electroluminescent device of the present invention, the resonant narrow spectrum fluorescent material is selected from the structures shown in any one of the following formulas (1), (2), (3), (4) or (5):
in the formula (1):
the R is 21 ～R 28 Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl or C5-C60 fused ring heteroaryl, and R 21 ～R 28 Wherein two adjacent groups are not connected or bonded to each other and form one of a C5-C30 five-membered or six-membered aryl ring and a C5-C30 five-membered or six-membered heteroaryl ring together with the adjacent benzene ring, and at least one hydrogen in the formed ring structure can be selected from the group consisting of C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, and C5-C60 fused ring arylAny one of condensed ring heteroaryl, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano and amino is substituted;
The X is 5 、X 6 Each independently selected from the group consisting of NR, the R may be bonded to the adjacent ring structure by-O-, -S-, -C (-R ') 2-, or a single bond, each of R and R' is independently selected from one of the following substituted or unsubstituted groups: C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C30 haloalkyl, C1-C30 alkoxy, C2-C30 alkenyl, C3-C30 alkynyl, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl;
in formula (1), ring F represents a group represented by B and X, respectively 5 A six-membered ring structure consisting of B and X 6 A group formed by fusing and connecting a six-membered ring structure, wherein the ring F is selected from one of a substituted or unsubstituted C6-C60 aromatic ring and a substituted or unsubstituted C5-C60 nitrogen-containing heteroaromatic ring;
when the above groups have substituents, the substituents are each independently selected from one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C3-C30 heteroaryl;
in the formula (2), the X 1 、X 2 、X 3 And X 4 Are each independently NR 1 Or O, and X 1 、X 2 、X 3 And X 4 Not simultaneously O, X 1 、X 2 、X 3 And X 4 Not at the same time NR 1 ；
The R is 1 One selected from the following substituted or unsubstituted groups: a C6-C60 monocyclic aryl group, a C6-C60 fused ring aryl group, a C5-C60 monocyclic heteroaryl group, or a C5-C60 fused ring heteroaryl group; the R is 1 With or without adjacent benzene rings by single bonds, or R 1 Condensed with adjacent benzene rings to bond with each other to form a ring;
the X is 1 And X is 4 The two can be connected by single bond, or can be thickBonded to each other to form a ring; the X is 2 And X is 3 The two can be connected by single bond or can be condensed to bond with each other to form a ring;
the R is a 、R b 、R c And R is d Each independently represents a single substituent to the maximum permissible substituent, and each is independently selected from hydrogen, deuterium, or one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, cave, perylene, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, tripolyphenyl, tetrabenzoyl, fluorenyl, spirobifluorenyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl; the R is a 、R b 、R c And R is d Optionally bonded to each other by single bond connection or disconnection, or by fusion to form a ring;
when the above groups have substituents, the substituents are each independently selected from any one of deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 fused ring heteroaryl;
in formula (3), the dotted line represents a single bond or no bond;
X 1 and X 2 Each independently is N or B;
ring A represents a benzene ring, naphthalene ring or anthracene ring;
ring B and ring C each independently represent a benzene ring, a naphthalene ring, or an anthracene ring;
ring D and ring E each independently represent a C8 to C60 fused aromatic hydrocarbon;
the R is A 、R B 、R C 、R D And R is E Each independently represents a substituent group from a monosubstituted group to a maximum allowable number of substituents, R A 、R B 、R C 、R D And R is E Each independently selected from one of hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, silicon-based, substituted or unsubstituted C1-C36 chain alkyl, substituted or unsubstituted C3-C36 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 thioalkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 monocyclic or fused ring aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C5-C60 heteroaryl;
The R is A 、R B 、R C 、R D And R is E Each of which is linked to the ring A, ring B, ring C, ring D and ring E by a single bond, or R A 、R B 、R C 、R D And R is E Each of which is fused to the attached ring A, ring B, ring C, ring D and ring E;
when R is as above A 、R B 、R C 、R D And R is E When a substituent is present, the substituent groups are independently selected from one of deuterium, halogen, nitro, cyano, amino, carbonyl, carboxyl, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl;
in the formulas (4) and (5), Y 1 And Y 2 Each independently is represented as O, S or N; a is that 1 、A 2 Each independently represents a single bond or O;
Z 1 -Z 12 represented as CR independently of each other 4 ；R 4 Each independently selected from any one of hydrogen, deuterium, C1-C10 alkyl, C3-C10 cycloalkyl and C6-C30 aryl;
the ring D is represented by hydrogen or a structure represented by the following formula (a) or (b), and the ring E is represented by the following formula (a) or (b):
in the formulae (a) and (b), the dotted line represents the connection position to the parent nucleus of the formula (1) or (2);
in the formula (a), Y 3 Represented by Y in formula (1) or formula (2) 1 And/or Y 2 ；
In the formula (a), X 1 -X 11 Represented as CR independently of each other 5 ；
In the formula (b), Y 4 Represented by Y in formula (1) or formula (2) 1 And/or Y 2 ，Y 5 Represent O, S or N;
in the formula (b), X 21 -X 35 Represented as CR independently of each other 7 ；
R 5 And R is 7 Each independently selected from any one of hydrogen, deuterium, C1-C10 alkyl, C3-C10 cycloalkyl and C6-C30 aryl;
preferably, in formula (1), ring F represents a substituted or unsubstituted C13-C60 nitrogen atom-containing heteroaromatic ring; in the formula (1), R 21 ～R 28 Each independently selected from the group consisting of hydrogen, deuterium, 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-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole-forming, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, tetraphenyl, tetrabipyrene, fluorenyl, spirobifrenyl, dihydrophenanthrenyl, dihydropyrrenyl, tetrahydroyl, cis-or trans-indenofluorenyl, trimeric indenyl, heterotrimindenyl, spiroisocyanatoindenyl, spiroisothenyl, furanyl, benzofuranyl, isobenzofuranyl, isobenzofuryl Pyranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthizolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridinyl, anthracenozolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, kazadienyl, kazanyl, kazazolyl, and kazazolyl 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylacridyl, one of (poly) halobenzene, (poly) cyanobenzene, (poly) trifluoromethylbenzene, etc., or a combination of the two groups.
Further, in the organic electroluminescent device of the present invention, the resonant narrow spectrum fluorescent material is selected from the structures shown in any one of the following formulas (6), (7), (8) and (9):
in the formula (6), R is selected from one of the following substituted or unsubstituted groups: C1-C10 alkyl, C6-C30 monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon; r is R 1 、R 2 、R 3 、R 4 、R 5 、R 5 、R 7 、R 8 、R 9 、R 10 Independently selected from the group consisting of hydrogen, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, hole, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, iso-trimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, pyrrolyl, isoindolyl, carbazole, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzofuranyl, and the like benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, napthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyrideazolyl, anthracenooxazolyl, phenanthroazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, carbozolyl, benzophenzolinyl, pyrrolinyl, phenanthroline, benzotriazole group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, 9-dimethylacridyl group, or a combination of the two groups;
In the formula (6), R 40 One selected from the group consisting of fluorophenyl, benzonitrile, substituted or unsubstituted triazinyl;
when the substituent groups exist in the groups, the substituent groups are respectively and independently selected from one of C1-C10 alkyl or cycloalkyl, C1-C6 alkoxy or thioalkoxy groups, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon groups, and C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon groups;
in the formulas (7), (8) and (9), X 1 And X 2 Each independently is N or B;
the R is B 、R C 、R D And R is E Each of which is connected to the linked ring structure by a single bond or by a fused connection.
The R is A 、R B 、R C 、R D And R is E Are each independently selected from the group consisting of hydrogen, deuterium, 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-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, and benzo-anthryl, phenanthryl, benzo-phenanthryl, pyrenyl, hole-yl, perylene, fluoranthenyl, naphthacene, pentacene, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, spiroisoperifenyl, spiro-or spirobifluorenyl furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthazenyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthazenyl, anthracenozolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl Pyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylacridyl, diarylamino, triarylamino, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, silicon-based, or a combination of two substituents selected from the above;
preferably, said R A 、R B 、R C 、R D And R is E Each independently selected from one of hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, adamantyl, fluoro, trifluoromethyl, phenyl, trimethylphenyl, naphthyl, anthryl, furyl, tetrahydrofuranyl, pyrrolyl, tetrahydropyrrolyl, thienyl, carbazolyl, triazinyl, pyridyl, quinolinyl, acridinyl, cyano, methoxy, silicon, dimethylamino, triarylamino, fluorenyl, dibenzofuranyl, dibenzothienyl, or a combination of the two substituents.
More preferably, in the organic electroluminescent device according to the present invention, the resonant narrow spectrum fluorescent material is selected from the following specific structural compounds, which are representative only:
12. the organic electroluminescent device of claim 1, wherein the phosphorescent sensitizer is selected from one of the following compounds:
more preferably, in the organic electroluminescent device of the present invention, the first host compound is selected from one of the following compounds:
more preferably, in the organic electroluminescent device of the present invention, the second host compound is selected from one of the following compounds:
further, in the organic electroluminescent device of the present invention, the doping concentration of the resonant narrow spectrum fluorescent material in the light emitting layer is 0.1wt% to 30wt%, and the doping concentration of the phosphorescent sensitizer in the light emitting layer is 1wt% to 50wt%;
preferably, the doping concentration of the resonance type narrow spectrum fluorescent material in the light-emitting layer is 0.1wt% to 10wt%, and the doping concentration of the phosphorescence sensitizer in the light-emitting layer is 1wt% to 20wt%;
more preferably, the doping concentration of the resonance type narrow spectrum fluorescent material in the light-emitting layer is 0.1-5wt%, and the doping concentration of the phosphorescence sensitizer in the light-emitting layer is 1-10wt%.
Still further, the invention protects the use of an organic electroluminescent device, which is in an organic electronic device comprising an optical sensor, a solar cell, an illumination element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper.
Further, the present invention provides a display device comprising the organic electroluminescent device of claim 1, wherein the display device is a display element, an illumination element, an information tag, an electronic artificial skin sheet, or electronic paper.
Drawings
Fig. 1 is a light emitting schematic diagram of an organic electroluminescent device according to the present invention, in which FET is Forster energy transfer, DET is Dexter energy transfer, ISC is intersystem crossing, and RISC is reverse intersystem crossing.
Fig. 2 is a schematic structural diagram of an organic electroluminescent device prepared in an embodiment of the present invention.
As shown in fig. 2, 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, which are sequentially deposited on a substrate 1.
Specifically, the substrate may be made of glass or a polymer material having excellent mechanical strength, thermal stability, water repellency, and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The anode may be formed by sputtering or depositing an anode material on the substrate, wherein the anode material may be an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or any combination thereof; the cathode may be made of metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The hole transport region, the light emitting layer, the electron transport region, and the organic material layer of the cathode may be sequentially prepared on the anode by vacuum thermal evaporation, spin coating, printing, and the like. Among them, the compound used as the organic material layer may be small organic molecules, large organic molecules, and polymers, and combinations thereof.
The hole transport region 3, the electron transport region 5, and the cathode 6 of the present invention will be described. The hole transport region 3 is located between the anode 2 and the organic light emitting layer 4. The hole transport region 3 may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region 3 may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region 3 (including HIL, HTL, and EBL) may be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers, or conductive dopant-containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives.
Among them, aromatic amine derivatives are compounds shown as HT-1 to HT-34 below. If the material of the hole transport region 3 is an aromatic amine derivative, it may be one or more of the compounds shown as HT-1 through HT-34.
The hole injection layer is located between the anode 2 and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-34 described above, or one or more of the compounds HI1 through HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1 to HI3 described below.
The electron transport region 5 may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region 5 may have a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-57 listed below.
The light emitting device may further include an electron injection layer between the electron transport layer and the cathode 6, the electron injection layer material including, but not limited to, one or more combinations of the following: liQ, liF, naCl, csF Li 2 O,Cs 2 CO 3 ,BaO,Na,Li,Ca。
The thickness of the layers described above may be conventional in the art.
Hereinafter, the light emitting layer will be described in detail. In the preparation of the organic light emitting layer 4, the organic light emitting layer 4 is formed by co-evaporation of a wide bandgap host material source, a TADF dye source, and a phosphorescent sensitizer material source.
The organic electroluminescent device according to the present invention will be further described by way of specific examples.
The preparation method of the organic electroluminescent device comprises the following steps:
1. the anode material coated glass plate was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
2. Placing the above glass plate with anode in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -3 Pa, vacuum evaporating a hole injection layer on the anode layer film, wherein the evaporation rate is 0.1-0.5nm/s;
3. vacuum evaporating a hole transport layer on the hole injection layer at an evaporation rate of 0.1-0.5nm/s,
4. and vacuum evaporating a light-emitting layer of the device on the hole transport layer, wherein the light-emitting layer comprises a host material, a TADF dye and a phosphorescence sensitizer. The evaporation rate of the main material and the evaporation rate of the TADF dye and the evaporation rate of the phosphorescent sensitizer material are regulated by utilizing a multisource co-evaporation method so that the dye reaches a preset doping proportion;
5. vacuum evaporating electron transport layer material of the device on the organic light emitting layer, wherein the evaporation rate is 0.1-0.5nm/s;
6. and (3) vacuum evaporation LiF with the concentration of 0.1-0.5nm/s is used as an electron injection layer on the electron transport layer, and vacuum evaporation Al with the concentration of 0.5-1nm/s is used as a cathode of the device.
Some organic materials adopted in the embodiment of the invention have the following structural formulas:
example 1
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode is ITO; the hole injection layer is made of HI-2, and the total thickness is generally 5-30nm, and the embodiment is 10nm; the hole transport layer is made of HI-27, and the total thickness is generally 5-500nm, in this embodiment 40nm; the main material of the organic light-emitting layer is the equimolar mixture of an exciplex D-2 and an exciplex A-01, the phosphorescent sensitizer material is PH-3, the doping concentration is 10wt%, the dye is a resonance TADF material MR-228, the doping concentration is 1wt%, and the thickness of the organic light-emitting layer is generally 1-200nm, and the embodiment is 30nm; the electron transport layer is made of ET-53, and the thickness is generally 5-300nm, and the thickness is 30nm in the embodiment; the electron injection layer and the cathode material are LiF (0.5 nm) and metallic aluminum (150 nm).
The device examples 1-85 and comparative examples 1-12 of the present invention were completed according to the above-described preparation steps and test methods, and the specific light-emitting layer designs are described in the following examples and table 1.
Example 2
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device has the same meaning as that of the embodiment 1, and the only difference is that the resonance type narrow spectrum fluorescent material is different.
Example 3
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-3:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device has the same meaning as that of the embodiment 1, and the only difference is that the resonance type narrow spectrum fluorescent material is different.
Example 4
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device has the same meaning as that of the embodiment 1, and the only difference is that the resonance type narrow spectrum fluorescent material is different.
Example 5
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device has the same meaning as that of the embodiment 1, and the only difference is that the resonance type narrow spectrum fluorescent material is different.
Example 6
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-5:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 7
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-5:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 8
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-5:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 9
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-5:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 10
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-5:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 11
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-67:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 12
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-67:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 13
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-67:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 14
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-67:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 15
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-01:10wt％PH-67:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in example 1, with the only difference that the phosphorescent sensitizer was different.
Example 16
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-3:A-08:10wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 1, with the only difference being the main body.
Example 17
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-3:A-08:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 2, with the only difference being the main body.
Example 18
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-3:A-08:10wt％PH-3:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 3, with the only difference being the main body.
Example 19
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-6:A-08:10wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 4, with the only difference being the main body.
Example 20
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-6:A-08:10wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 5, with the only difference being the main body.
Example 21
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-6:A-08:10wt％PH-5:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 6, with the only difference being the main body.
Example 22
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-3:A-08:10wt％PH-5:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 7, with the only difference being the main body.
Example 23
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-3:A-09:10wt％PH-5:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 8, with the only difference being the main body.
Example 24
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-6:A-09:10wt％PH-5:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device sense is substantially the same as that of example 9, with the only difference that the main body is different.
Example 25
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-6:A-09:10wt％PH-5:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 10, with the only difference being the main body.
Example 26
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-09:10wt％PH-67:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 11, with the only difference being the main body.
Example 27
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-2:A-09:10wt％PH-67:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 12, with the only difference being the main body.
Example 28
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-6:A-01:10wt％PH-67:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device sense was substantially the same as in example 13, with the only difference being the main body.
Example 29
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-6:A-01:10wt％PH-67:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 14, with the only difference being the main body.
Example 30
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-3:A-01:10wt％PH-67:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 15, with the only difference being the main body.
Example 31
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 5, with the only difference being the main body.
Example 32
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance is almost the same as that of the embodiment 31, and the only difference is that the resonance type narrow spectrum fluorescent material is different.
Example 33
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance is almost the same as that of the embodiment 31, and the only difference is that the resonance type narrow spectrum fluorescent material is different.
Example 34
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-18:10wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 1, with the only difference being the main body.
Example 35
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-18:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 2, with the only difference being the main body.
Example 36
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-36:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 35, with the only difference being the main body.
Example 37
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-36:10wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 33, with the only difference being the main body.
Example 38
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-36:10wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 31, with the only difference being the main body.
Example 39
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-36:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 35, with the only difference being the main body.
Example 40
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-5:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 6, with the only difference being the main body.
Example 41
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-5:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 7, with the only difference being the main body.
Example 42
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-5:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 8, with the only difference being the main body.
Example 43
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-5:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device sense is substantially the same as that of example 9, with the only difference that the main body is different.
Example 44
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-5:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 10, with the only difference being the main body.
Example 45
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-18:10wt％PH-67:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device sense was substantially the same as in example 13, with the only difference being the main body.
Example 46
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-67:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 40, with the only difference being the phosphorescent sensitizer.
Example 47
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-67:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 41, with the only difference that the phosphorescent sensitizer was different.
Example 48
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-67:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 42, with the only difference being the phosphorescent sensitizer.
Example 49
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-67:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 43, with the only difference that the phosphorescent sensitizer was different.
Example 50
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-67:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 44, with the only difference being the phosphorescent sensitizer.
Example 51
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:15wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 31, with the only difference that the doping concentration of the phosphorescent sensitizer is different.
Example 52
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:20wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 41, the only difference being the doping concentration of the phosphorescent sensitizer.
Example 53
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:25wt％PH-67:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 48, with the only difference being the doping concentration of the phosphorescent sensitizer.
Example 54
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:30wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 32, with the only difference being the doping concentration of the phosphorescent sensitizer.
Example 55
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:5wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 33, the only difference being the doping concentration of the phosphorescent sensitizer.
Example 56
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-27:10wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as that of embodiment 32, with the only difference being the main body.
Example 57
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-27:10wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 33, with the only difference being the main body.
Example 58
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-27:10wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 3, with the only difference being the main body.
Example 59
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-27:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 35, with the only difference being the main body.
Example 60
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-18:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in embodiment 36, with the only difference being the main body.
Example 61
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-18:10wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 37, with the only difference being the main body.
Example 62
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-18:10wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as that of embodiment 38, with the only difference being the main body.
Example 63
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-27:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in embodiment 39, with the only difference being the main body.
Example 64
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-36:10wt％PH-5:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as embodiment 40, with the only difference being the main body.
Example 65
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-25:A-36:10wt％PH-5:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in embodiment 41, with the only difference being the main body.
Example 66
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-36:10wt％PH-5:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as embodiment 42, with the only difference being the main body.
Example 67
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-36:10wt％PH-67:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 48, with the only difference being the main body.
Example 68
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-36:10wt％PH-67:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in embodiment 39, with the only difference being the main body.
Example 69
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-3:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 1, with the only difference being the main body.
Example 70
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-3:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 2, with the only difference being the main body.
Example 71
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-3:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 3, with the only difference being the main body.
Example 72
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-3:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 4, with the only difference being the main body.
Example 73
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 5, with the only difference being the main body.
Example 74
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-5:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 6, with the only difference being the main body.
Example 75
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-5:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 7, with the only difference being the main body.
Example 76
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-5:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 8, with the only difference being the main body.
Example 77
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-5:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device sense is substantially the same as that of example 9, with the only difference that the main body is different.
Example 78
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-5:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 10, with the only difference being the main body.
Example 79
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-67:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 11, with the only difference being the main body.
Example 80
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-67:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 12, with the only difference being the main body.
Example 81
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-67:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance is almost the same as that of the embodiment 31, and the only difference is that the doping concentration of the resonance type narrow spectrum fluorescent material is different.
Example 82
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-67:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance is approximately the same as that of the embodiment 33, and the only difference is that the doping concentration of the resonance type narrow spectrum fluorescent material is different.
Example 83
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-53:A-44:10wt％PH-67:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as that of example 50, with the only difference that the doping concentration of the resonant narrow spectrum fluorescent material is different.
Example 84
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-75:A-59:10wt％PH-5:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as that of example 42, with the only difference that the doping concentration of the resonant narrow spectrum fluorescent material is different.
Example 85
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-75:A-82:10wt％PH-5:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as that of example 44, with the only difference that the doping concentration of the resonant narrow spectrum fluorescent material is different.
Example 86
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-240:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 31, with the only difference that the phosphorescent sensitizer was different.
Example 87
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-241:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 43, with the only difference that the phosphorescent sensitizer was different.
Example 88
The device structure of this embodiment is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:10wt％PH-242:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was essentially the same as in example 52, with the only difference being the phosphorescent sensitizer.
Comparative example 1
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 43, with the only difference that no phosphorescent sensitizer is present.
Comparative example 2
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 44, with the only difference that no phosphorescent sensitizer is present.
Comparative example 3
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 41, with the only difference that no phosphorescent sensitizer is present.
Comparative example 4
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％MR-10(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 42, with the only difference that no phosphorescent sensitizer is present.
Comparative example 5
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％MR-228(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device is substantially the same as in example 40, with the only difference that no phosphorescent sensitizer is present.
Comparative example 6
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％TBPe(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in comparative example 31, with the only difference that the light-emitting layer was replaced with a conventional fluorescent dye.
Comparative example 7
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％TTPA(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in comparative example 31, with the only difference that the light-emitting layer was replaced with a conventional fluorescent dye.
Comparative example 8
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％TBRb(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in comparative example 31, with the only difference that the light-emitting layer was replaced with a conventional fluorescent dye.
Comparative example 9
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/D-14:A-18:1wt％DBP(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance was approximately the same as in comparative example 31, with the only difference that the light-emitting layer was replaced with a conventional fluorescent dye.
Comparative example 10
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/W-7:10wt％PH-3:1wt％MR-82(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance is substantially the same as in example 5, the only difference being that the body is replaced by a wide bandgap body.
Comparative example 11
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/W-19:10wt％PH-5:1wt％MR-802(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance is substantially the same as in example 9, the only difference being that the body is replaced by a wide bandgap body.
Comparative example 12
The device structure of this comparative example is as follows:
ITO/HI-2(10nm)/HT-27(40nm)/W-1:10wt％PH-67:1wt％MR-1217(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)
the device significance is substantially the same as in example 27, the only difference being that the body is replaced by a wide bandgap body.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the following performance measurements were performed on the devices prepared in examples 1 to 85 and comparative examples 1 to 12: the characteristics of the prepared device such as current, voltage, brightness, luminescence spectrum, current efficiency, external quantum efficiency and the like are synchronously tested by adopting a PR 655 spectrum scanning luminance meter and a Keithley K2400 digital source meter system, and the service life is finished through an MC-6000 test.
1. Switching on voltage: increasing the voltage at a rate of 0.1V per second, and determining that the brightness of the organic electroluminescent device reaches 1cd/m 2 The voltage at that time is the turn-on voltage;
2. the lifetime test of LT90 is as follows: and obtaining a brightness and service life decay curve of the organic electroluminescent device by setting different test brightness, thereby obtaining the service life value of the device under the condition of requiring the decay brightness. I.e. the test brightness is set to 1000cd/m 2 Maintaining constant current, and measuring brightness drop of the organic electroluminescent device to 900cd/m 2 Time in hours;
the specific test results are shown in Table 1.
Table 1:
the electroluminescent external quantum efficiency of the organic electroluminescent device structure is about 30%, and the efficiency roll-off is small under high brightness, and the half-peak width is narrower, so that the color purity is good. In addition, the device of the invention has longer service life and shows overall superiority.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device. The display device can be a display device such as an OLED display, and any product or component with a display function such as a television, a digital camera, a mobile phone, a tablet personal computer and the like comprising the display device. The display device has the same advantages as the organic electroluminescent device described above with respect to the prior art, and will not be described in detail herein.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same. Although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may be modified or some or all of the technical features may be replaced with other technical solutions, which do not depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (14)
1. An organic electroluminescent device comprising a substrate, a first electrode, a second electrode and an organic functional layer, wherein the organic functional layer comprises an organic luminescent layer, the organic luminescent layer comprises a main body material, a phosphorescent sensitizer and a resonant narrow-spectrum fluorescent material used as a luminescent dye, and the organic electroluminescent device is characterized in that:
The host material is composed of a first host compound and a second host compound, and the first host compound and the second host compound form an exciplex;
the resonance type narrow spectrum fluorescent material is a material with narrow band spectrum emission characteristics, and Stokes displacement of the resonance type narrow spectrum fluorescent material meets the following conditions: lambda is less than or equal to 60nm, and half-peak width meets the following conditions: FWHM is less than or equal to 60nm;
the resonance type narrow spectrum fluorescent material is a compound with a core structure adopting a resonance molecular structure formed by boron atoms and nitrogen atoms, or a compound with a core structure adopting a resonance molecular structure formed by boron atoms, oxygen, sulfur and selenium atoms, or a compound with a core structure adopting a resonance molecular structure formed by carbonyl groups and nitrogen atoms, or a compound with a core structure adopting a resonance molecular structure formed by carbonyl groups, oxygen, sulfur and selenium atoms, or a compound with a core structure adopting an indolocarbazole resonance molecular structure, and the singlet energy level S1 and the triplet energy level T1 of the resonance type narrow spectrum fluorescent material satisfy the formula:
ΔEst＝S1-T1≤0.4eV；
the singlet energy level and the triplet energy level of the second host compound are higher than those of the phosphorescent sensitizer, and the singlet energy level and the triplet energy level of an exciplex formed by the first host compound and the second host compound are also higher than those of the phosphorescent sensitizer;
The triplet state energy level of the exciplex is higher than that of the resonance type narrow spectrum fluorescent material;
the triplet state energy level of the phosphorescence sensitizer is higher than that of the resonance type narrow spectrum fluorescent material.
2. The organic electroluminescent device of claim 1, wherein the first host compound is a hole transporting host having a highest occupied track E HOMO P And the lowest unoccupied track E LUMO P Having a first singlet energy level S 1 P And a first triplet energy level T 1 P (calculated from the Oset values of the fluorescence emission spectrum and the phosphorescence emission spectrum at 77K);
the second host compound is an electron transport host and has the highest occupied track E HOMO N And the lowest unoccupied track E LUMO N Having a first singlet energy level S 1 N And a first triplet energy level T 1 N (calculated from the Oset values of the fluorescence emission spectrum and the phosphorescence emission spectrum at 77K);
the exciplex formed by the first host compound and the second host compound has a first singlet energy level S 1 EX And a first triplet energy level T 1 EX (calculated from the set values of the fluorescence emission spectrum and the phosphorescence emission spectrum at 77K), the first host compound, the second host compound and the formed exciplex satisfy the following equation:
S 1 EX ━T 1 EX ≤0.3Ev；
E HOMO P ＞E HOMO N ；
E LUMO P ＞E LUMO N ；
E HOMO P －E HOMO N ＞0.2eV；
E LUMO P －E LUMO N ＞0.3eV；
S 1 P ＞S 1 N ≧S 1 EX 。
3. The organic electroluminescent device of claim 1, wherein the phosphorescent sensitizer has a first singlet energy level S 1 Phos And a first triplet energy level T 1 Phos (S 1 Phos Calculated according to Oset value of tail absorption in the longest wavelength direction of ultraviolet visible absorption spectrum, T 1 Phos Calculated from the Onset value of the phosphorescence emission spectrum at 77K), the following equation is satisfied:
S 1 EX ＞S 1 Phos
T 1 EX ＞T 1 Phos 。
4. the organic electroluminescent device of claim 1, wherein the first host compound is selected from the group consisting of compounds represented by the following formulas 1-1:
in the formula (1-1), the Ar 4 One selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R 001 and R is 002 A substituent group representing a single substitution up to the allowable number, R 001 And R is 002 Each independently selected from one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; and R is 001 、R 002 Are not connected or are connected into a ring between two adjacent to each other;
when substituents are present on the above groups, the substituents are each independently selected from any one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryloxy, C6-C60 aryl, C5-C60 heteroaryl.
5. The organic electroluminescent device of claim 4, wherein the first host compound has a structure according to formula (1-2) or formula (1-3):
in the formula (1-2) and the formula (1-3), m and n are each independently integers of 1-4;
the Ar is as follows 4 、R 001 And R is 002 Is the same as that in formula (1-1);
the Ar is as follows 5 One selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
the L is selected from one of single bond, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R 003 、R 004 a substituent group representing a single substitution up to the allowable number, R 001 And R is 002 Each independently selected from one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
When substituents are present on the above groups, the substituents are each independently selected from any one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryloxy, C6-C60 aryl, C5-C60 heteroaryl;
preferably, the Ar 4 、Ar 5 Each independently selected from one or more of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted indole, substituted or unsubstituted indolocarbazole, substituted or unsubstituted carbazole, substituted or unsubstituted fluorene; when Ar is 4 、Ar 5 When a substituent is present on the aromatic hydrocarbon, the substituent is independently selected from any one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl and C5-C30 heteroaryl.
6. The organic electroluminescent device of claim 1 or 4, wherein the first host compound is selected from one of the following compounds:
7. The organic electroluminescent device of claim 1, wherein the second host compound is selected from one of the following compounds:
8. the organic electroluminescent device according to claim 1, wherein the resonant narrow spectrum fluorescent material is selected from a structure represented by any one of the following formulas (1), (2), (3), (4) or (5):
in the formula (1):
the R is 21 ～R 28 Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl or C5-C60 fused ring heteroaryl, and R 21 ～R 28 Wherein two adjacent groups are not connected or bonded to each other and form one of a C5-C30 five-membered or six-membered aryl ring and a C5-C30 five-membered or six-membered heteroaryl ring together with an adjacent benzene ring, and at least one hydrogen in the formed ring structure may be substituted by any one of a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C60 monocyclic aryl group, a C6-C60 fused ring aryl group, a C6-C60 aryloxy group, a C5-C60 monocyclic heteroaryl group, a C5-C60 fused ring heteroaryl group, halogen, a C1-C30 chain alkyl group, a C3-C30 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 thioalkoxy group, carbonyl group, carboxyl group, nitro group, cyano group and amino group;
The X is 5 、X 6 Each independently selected from the group consisting of NR, the R may be bonded to the adjacent ring structure by-O-, -S-, -C (-R ') 2-, or a single bond, each of R and R' is independently selected from one of the following substituted or unsubstituted groups: C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C30 haloalkyl, C1-C30 alkoxy, C2-C30 alkenyl, C3-C30 alkynyl, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl;
in formula (1), ring F representsAt the same time with B and X respectively 5 A six-membered ring structure consisting of B and X 6 A group formed by fusing and connecting a six-membered ring structure, wherein the ring F is selected from one of a substituted or unsubstituted C6-C60 aromatic ring and a substituted or unsubstituted C5-C60 nitrogen-containing heteroaromatic ring;
when the above groups have substituents, the substituents are each independently selected from one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C3-C30 heteroaryl;
in the formula (2), the X 1 、X 2 、X 3 And X 4 Are each independently NR 1 Or O, and X 1 、X 2 、X 3 And X 4 Not simultaneously O, X 1 、X 2 、X 3 And X 4 Not at the same time NR 1 ；
The R is 1 One selected from the following substituted or unsubstituted groups: a C6-C60 monocyclic aryl group, a C6-C60 fused ring aryl group, a C5-C60 monocyclic heteroaryl group, or a C5-C60 fused ring heteroaryl group; the R is 1 With or without adjacent benzene rings by single bonds, or R 1 Condensed with adjacent benzene rings to bond with each other to form a ring;
the X is 1 And X is 4 The two can be connected by single bond or can be condensed to bond with each other to form a ring; the X is 2 And X is 3 The two can be connected by single bond or can be condensed to bond with each other to form a ring;
the R is a 、R b 、R c And R is d Each independently represents a single substituent to the maximum permissible substituent, and each is independently selected from hydrogen, deuterium, or one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenylBenzophenanthryl, pyrenyl, hole, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, tripolyphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl; the R is a 、R b 、R c And R is d Optionally bonded to each other by single bond connection or disconnection, or by fusion to form a ring;
when the above groups have substituents, the substituents are each independently selected from any one of deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 fused ring heteroaryl;
in formula (3), the dotted line represents a single bond or no bond;
X 1 and X 2 Each independently is N or B;
ring A represents a benzene ring, naphthalene ring or anthracene ring;
ring B and ring C each independently represent a benzene ring, a naphthalene ring, or an anthracene ring;
ring D and ring E each independently represent a C8 to C60 fused aromatic hydrocarbon;
the R is A 、R B 、R C 、R D And R is E Each independently represents a substituent group from a monosubstituted group to a maximum allowable number of substituents, R A 、R B 、R C 、R D And R is E Each independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, silicon-based, substituted or unsubstituted C1-C36 chain alkyl, substituted or unsubstituted C3-C36 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 thioalkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 monocyclic or fused ring aryl, substituted or unsubstituted C6-C60 aryloxy, substituted Or one of unsubstituted C5-C60 heteroaryl;
the R is A 、R B 、R C 、R D And R is E Each of which is linked to the ring A, ring B, ring C, ring D and ring E by a single bond, or R A 、R B 、R C 、R D And R is E Each of which is fused to the attached ring A, ring B, ring C, ring D and ring E;
when R is as above A 、R B 、R C 、R D And R is E When a substituent is present, the substituent groups are independently selected from one of deuterium, halogen, nitro, cyano, amino, carbonyl, carboxyl, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl;
in the formulas (4) and (5), Y 1 And Y 2 Each independently is represented as O, S or N; a is that 1 、A 2 Each independently represents a single bond or O;
Z 1 -Z 12 represented as CR independently of each other 4 ；R 4 Each independently selected from any one of hydrogen, deuterium, C1-C10 alkyl, C3-C10 cycloalkyl and C6-C30 aryl;
the ring D is represented by hydrogen or a structure represented by the following formula (a) or (b), and the ring E is represented by the following formula (a) or (b):
in the formulae (a) and (b), the dotted line represents the connection position to the parent nucleus of the formula (1) or (2);
In the formula (a), Y 3 Represented by Y in formula (1) or formula (2) 1 And/or Y 2 ；
In the formula (a), X 1 -X 11 Represented as CR independently of each other 5 ；
In the formula (b), Y 4 Representative ofY in formula (1) or formula (2) 1 And/or Y 2 ，Y 5 Represent O, S or N;
in the formula (b), X 21 -X 35 Represented as CR independently of each other 7 ；
R 5 And R is 7 Each independently selected from any one of hydrogen, deuterium, C1-C10 alkyl, C3-C10 cycloalkyl and C6-C30 aryl;
preferably, in formula (1), ring F represents a substituted or unsubstituted C13-C60 nitrogen atom-containing heteroaromatic ring; in the formula (1), R 21 ～R 28 Are each independently selected from the group consisting of hydrogen, deuterium, 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-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, and benzo-anthryl, phenanthryl, benzo-phenanthryl, pyrenyl, hole-yl, perylene, fluoranthenyl, naphthacene, pentacene, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, spiroisoperifenyl, spiro-or spirobifluorenyl furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthazenyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthazenyl, anthracenozolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1,6- The group selected from the group consisting of diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2, 3-tetrazolyl, 1, 3-tetrazolyl, 3-oxazinyl, 1, 9-thiadiazinyl, (poly) benzodiazine, (poly) cyano, poly (methyl) and the like, poly (fluoro) groups, poly (o) is selected from the group consisting of poly (meth) benzodiazine).
9. The organic electroluminescent device according to claim 1, wherein the resonant narrow spectrum fluorescent material is selected from a structure represented by any one of the following formulas (6), (7), (8) and (9):
in the formula (6), R is selected from one of the following substituted or unsubstituted groups: C1-C10 alkyl, C6-C30 monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon; r is R 1 、R 2 、R 3 、R 4 、R 5 、R 5 、R 7 、R 8 、R 9 、R 10 Independently selected from the group consisting of hydrogen, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, hole, perylene, fluorantheyl, naphthacene, pentacene, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, iso-trimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, Isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, napthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl one of benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, benzotriazole, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylacridyl, or a combination of two groups selected from the above;
In the formula (6), R 40 One selected from the group consisting of fluorophenyl, benzonitrile, substituted or unsubstituted triazinyl;
when the substituent groups exist in the groups, the substituent groups are respectively and independently selected from one of C1-C10 alkyl or cycloalkyl, C1-C6 alkoxy or thioalkoxy groups, C6-C30 monocyclic aromatic hydrocarbon or condensed ring aromatic hydrocarbon groups, and C3-C30 monocyclic heteroaromatic hydrocarbon or condensed ring heteroaromatic hydrocarbon groups;
in the formulas (7), (8) and (9), X 1 And X 2 Each independently is N or B;
the R is B 、R C 、R D And R is E Each of which is connected to the linked ring structure by a single bond or by a fused connection.
The R is A 、R B 、R C 、R D And R is E Are each independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butylPhenyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole-yl, perylene, fluoranthenyl, naphthacene, pentacene, benzopyrene, biphenyl, even phenyl, terphenyl, trimeric phenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, spirotrimeric indenyl, spiroheterotriminanyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, benzopyrene, spiroisopyrene Isobenzothioyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, napthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridazolyl, anthraoxazolyl, phenanthroazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, and phenanthroline group, 1,2, 3-triazole group, 1,2, 4-triazole group, benzotriazole group, 1,2, 3-oxadiazole group, 1,2, 4-oxadiazole group, 1,2, 5-oxadiazole group, 1,2, 3-thiadiazole group, and 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylacridyl, diarylaminyl, triarylamino, adamantane, fluorobenzene One of the groups selected from methyl phenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy and silicon base, or a combination of the two substituent groups;
preferably, said R A 、R B 、R C 、R D And R is E Each independently selected from one of hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, adamantyl, fluoro, trifluoromethyl, phenyl, trimethylphenyl, naphthyl, anthryl, furyl, tetrahydrofuranyl, pyrrolyl, tetrahydropyrrolyl, thienyl, carbazolyl, triazinyl, pyridyl, quinolinyl, acridinyl, cyano, methoxy, silicon, dimethylamino, triarylamino, fluorenyl, dibenzofuranyl, dibenzothienyl, or a combination of the two substituents.
10. The organic electroluminescent device of claim 1, wherein the resonant narrow spectrum fluorescent material is selected from the following specific structural compounds, which are representative only:
11. the organic electroluminescent device of claim 1, wherein the phosphorescent sensitizer is selected from one of the following compounds:
12. the organic electroluminescent device according to claim 1, wherein the doping concentration of the resonant narrow spectrum fluorescent material in the light emitting layer is 0.1wt% to 30wt%, and the doping concentration of the phosphorescent sensitizer in the light emitting layer is 1wt% to 50wt%;
Preferably, the doping concentration of the resonance type narrow spectrum fluorescent material in the light-emitting layer is 0.1wt% to 10wt%, and the doping concentration of the phosphorescence sensitizer in the light-emitting layer is 1wt% to 20wt%;
more preferably, the doping concentration of the resonance type narrow spectrum fluorescent material in the light-emitting layer is 0.1-5wt%, and the doping concentration of the phosphorescence sensitizer in the light-emitting layer is 1-10wt%.
13. Use of the organic electroluminescent device according to claim 1, characterized in that the use is in an organic electronic device comprising an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper.
14. A display device comprising the organic electroluminescent device of claim 1, wherein the display device is a display element, an illumination element, an information tag, an electronic artificial skin sheet, or electronic paper.
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