CN111548353B - Organic luminescent material and organic electroluminescent device - Google Patents
Organic luminescent material and organic electroluminescent device Download PDFInfo
- Publication number
- CN111548353B CN111548353B CN202010453418.3A CN202010453418A CN111548353B CN 111548353 B CN111548353 B CN 111548353B CN 202010453418 A CN202010453418 A CN 202010453418A CN 111548353 B CN111548353 B CN 111548353B
- Authority
- CN
- China
- Prior art keywords
- organic
- reaction
- luminescent material
- organic luminescent
- electroluminescent device
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 71
- 230000005525 hole transport Effects 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 11
- 239000007924 injection Substances 0.000 abstract description 11
- 230000002349 favourable effect Effects 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 238000013508 migration Methods 0.000 abstract description 4
- 230000005012 migration Effects 0.000 abstract description 4
- 238000009825 accumulation Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 18
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- -1 dibenzofuranyl Chemical group 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- UYTRBIUOIKOGQO-UHFFFAOYSA-N 2-bromo-1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Br UYTRBIUOIKOGQO-UHFFFAOYSA-N 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000005580 triphenylene group Chemical group 0.000 description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- AFGJVJRQAZXHGK-UHFFFAOYSA-N CC1(C)c2ccccc2-c2cccc(N)c12 Chemical compound CC1(C)c2ccccc2-c2cccc(N)c12 AFGJVJRQAZXHGK-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BIECSXCXIXHDBC-UHFFFAOYSA-N methyl 2-bromo-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Br BIECSXCXIXHDBC-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007547 defect Effects 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
- 238000013461 design Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to an organic luminescent material, which has a structure shown in the following general formula (I):
Description
Technical Field
The invention relates to an organic luminescent material and an organic electroluminescent device, belonging to the technical field of luminescent materials.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light under the excitation of electric current and electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (OLED) has the advantages of self-luminescence, low voltage DC drive, full solidification, wide viewing angle, light weight, simple composition and process, etc., compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle and low power, the response speed can reach 1000 times of the liquid crystal display, and the manufacturing cost is lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advancement of OLED technology in the two fields of illumination and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is usually the result of the optimized collocation of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, film can be formed on any substrate by a vapor deposition or spin coating method, and flexible display and large-area display can be realized; the optical property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of the molecule, and the material has a large space to select. In the most common OLED device structures, the following classes of organic materials are typically included: a hole injection material, a hole transport material, an electron transport material, a light emitting material (dye or doped guest material) of each color, a corresponding host material, and the like.
Disclosure of Invention
The invention provides an organic luminescent material and an organic electroluminescent device using the same, aiming at the defects of the prior art.
The technical scheme for solving the technical problems is as follows: an organic light-emitting material having a structure represented by the following general formula (I):
wherein Ar is 1 ，Ar 2 Selected from C unsubstituted or substituted by Ra 6 -C 30 An aromatic group of (a);
R 1 -R 4 identical or different and independently of one another selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl, wherein, adjacent R 1 -R 4 Can be connected into a ring;
l is selected from chemical bond, C 6 -C 30 Or C 3 -C 30 Is a heteroarylene group;
x and Y are selected from O, S, CR 5 R 6 、NR 7 ；
R 5 、R 6 Independently selected from C 1 -C 10 Alkyl, C 1 -C 6 Cycloalkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl; r is R 7 Selected from C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl;
a is selected from the group consisting of formula (II) wherein Z 1 -Z 8 Any one of the (B) is a connecting site of a formula (II) and a formula (I);
Z 1 -Z 8 selected from CR or N, R is selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, wherein adjacent R can be connected to form a ring;
the substituents Ra of the various groups are the same or different and are independently selected from hydrogen, halogen, nitro, cyano, C 1 -C 4 Alkyl group of (C),Phenyl, biphenyl, terphenyl, or naphthyl.
Preferably, said Ar 1 ，Ar 2 Selected from any one of the following substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, and carbazolyl.
Preferably, said R 1 -R 4 Independently of each other, selected from any of the following groups, which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably, said R 5 And R is 6 Independently of each other, selected from any one of the following groups, which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably, said R 7 Any one of the following groups, which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinolylAn oxinyl group, cinnolinyl group, naphthyridinyl group, triazinyl group, pyridopyrazinyl group, furyl group, benzofuryl group, dibenzofuryl group, aza-dibenzofuryl group, thienyl group, benzothienyl group, dibenzothienyl group, aza-dibenzothienyl group, 9-dimethylfluorenyl group, spirofluorenyl group, arylamine, carbazole group.
Preferably, L is selected from a bond, or a subunit of any one of the following compounds, unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
Preferably, said R is selected from hydrogen, methyl, ethyl, cyclopentyl, cyclohexyl, any one of the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably, the organic light emitting material is selected from any one of the following compounds A1 to a 30:
the invention also discloses an organic electroluminescent device, which comprises the organic luminescent material.
The organic light emitting material is used as a hole transporting material of the organic electroluminescent device.
The beneficial effects of the invention are as follows:
the organic luminescent material disclosed by the invention has a parent structure of diversified condensed heterocycles, has high bond energy among atoms and good thermal stability, and can effectively reduce the voltage of a device and prolong the service life of the material when being used as a hole transport layer material.
The organic luminescent material is a derivative of diversified condensed heterocycles, is applied to a hole transport layer, has proper energy level with adjacent layers, is favorable for hole injection and migration, can effectively reduce the starting voltage, has higher hole migration rate, and can realize good luminous efficiency in a device. The compound provided by the invention has a larger conjugate plane, is favorable for molecular accumulation, shows good thermodynamic stability, and shows long service life in a device.
Meanwhile, the preparation process of the organic luminescent material is simple and feasible, raw materials are easy to obtain, and the organic luminescent material is suitable for industrial production.
Detailed Description
The following detailed description of the present invention will provide further details in order to make the above-mentioned objects, features and advantages of the present invention more comprehensible. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. The present invention may be embodied in many other forms than described herein and similarly modified by those skilled in the art without departing from the spirit of the invention, whereby the invention is not limited to the specific embodiments disclosed below.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The organic luminescent material can be used as a hole transport material in an organic electroluminescent device.
In the present application, the kind and structure of the organic electroluminescent device are not particularly limited as long as the organic luminescent material provided in the present application can be used. For convenience, the present application will be described with respect to an organic light emitting diode, but this is not meant to limit the scope of the present application in any way. It is understood that all organic electroluminescent devices capable of using the organic luminescent material of the present invention are within the scope of the present invention.
In general, an organic light emitting diode includes first and second electrodes on a substrate, and an organic material layer between the electrodes, and the organic material layer may have a multi-layered structure. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
In the present application, the substrate is not particularly limited, and conventional substrates used in the organic electroluminescent device in the related art, for example, glass, polymer materials, glass with TFT devices, polymer materials, and the like can be used.
In the present application, the anode material is not particularly limited, and may be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) The transparent conductive material such as zinc oxide (ZnO), the metal material such as silver and its alloy, aluminum and its alloy, the organic conductive material such as PEDOT (poly 3, 4-ethylenedioxythiophene), the multilayer structure of the above materials, and the like.
In the present application, the cathode material is not particularly limited, and may be selected from, for example, materials such as magnesium silver mixture, liF/Al, ITO, etc., metal mixtures, oxides, etc.
In this application, the organic electroluminescent diode (OLED) may further include a hole injection layer, a hole transport layer, etc. between the light emitting layer and the anode, and these layers may be used, but are not limited to, at least one of HT-1 to HT-31 listed below, and these materials may be used singly or in combination of two or more.
In the present application, the device light-emitting layer may comprise a host material and a light-emitting dye, wherein the host material includes, but is not limited to, a combination of one or more of the conventional materials shown in GPH-1 through GPH-80, below.
In a preferred embodiment of the present invention, the light-emitting layer employs phosphorescence-electroluminescence technology. The light emitting layer thereof is doped with a phosphorescent dopant which may be selected from, but is not limited to, one or more combinations of the below listed RPD-1 through RPD-28.
The electron transport material includes, but is not limited to, a combination of one or more of the following listed ET-1 to ET-57 materials. The electron transport materials of the present application may be used in combination with one or more of these materials.
In addition, the OLED device may further include an electron injection layer between the electron transport layer and the cathode, the material of the electron injection layer is not particularly limited, and may include, for example, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 BaO, na, li, ca, etc. or a combination of several materials.
In this application, HT-28 was used for comparison experiments with the organic luminescent materials of the present invention.
The method for synthesizing the compound of the present application is not particularly limited, and may be synthesized by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
Synthesis example 1: synthesis of Compound A1
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 1-dibenzofuran boric acid, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into the reaction flask were charged 100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorene) -4-aminobiphenyl, 40g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-tert-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with xylene to obtain yellow powder A1. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
M/Z: theory, 692.86; experimental values, 692.3.
1 H NMR(400MHz,Chloroform)δ8.16-8.02(m,2H),7.90-7.75(m,4H),7.62(s,1H),7.61–7.46(m,6H),7.43–7.29(m,4H),7.24(s,1H),7.19(d,J＝7.2Hz,8H),7.01-6.83(m,4H),1.69(s,6H).
Synthesis example 2: synthesis of Compound A5
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 1-dibenzothiophene boronic acid, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into the reaction flask were charged 100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorenamine) -3- (N-phenylcarbazole), 40g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with xylene to obtain yellow powder A5. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ8.19(d,J＝9.2Hz,2H),7.92(dd,J＝12.0,8.4Hz,4H),7.63(d,J＝10.8Hz,3H),7.57(d,J＝10.0Hz,3H),7.49(d,J＝10.0Hz,2H),7.40(s,1H),7.38–7.29(m,7H),7.24(s,1H),7.19(d,J＝10.0Hz,4H),7.01-6.88(m,6H),1.69(s,6H).
M/Z: theory, 798.02; experimental values, 797.8.
Synthesis example 3: synthesis of Compound A9
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 4-N-phenylcarbazole boron ester, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, and passingThe solid obtained was purified by recrystallization from toluene after filtration and washing with water to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into the reaction flask were charged 100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorenamine) -2- (dibenzothiophene), 40g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization from xylene to obtain yellow powder A9. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
1 H NMR(400MHz,Chloroform)δ8.50(d,J＝10.0Hz,2H),7.90(s,1H),7.80(d,J＝8.4Hz,3H),7.71–7.54(m,5H),7.54–7.48(m,4H),7.42–7.14(m,6H),7.09(d,J＝12.0Hz,4H),7.01(s,1H),6.58-6.40(m,7H),1.69(s,6H).
M/Z: theory, 798.02; experimental values, 797.9.
Synthesis example 4: synthesis of Compound A17
Into a reaction flask were charged 100mmol of 2-bromo-3-chloro-nitrobenzene, 100mmol of 4-N-phenylcarbazole boron ester, 40g of potassium carbonate (300 mmol), 800ml THF and 200ml water, and 1mol% Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M1. Wherein Pd (PPh) 3 ) 4 The amount of the catalyst to be added was 1mol% of 2-bromo-3-chloro-nitrobenzene.
M1 (100 mmol,1 eq) and triphenylphosphine (300 mmol,1 eq) were reacted for 12h under reflux with 800ml o-dichlorobenzene. After the reaction, the solvent was distilled off, and the intermediate M2 was obtained by column chromatography.
To the reaction flask were added 100mmol of M2, 100mmol of bromobenzene, 40g of sodium t-butoxide (300 mmol), 800ml of toluene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 100℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M3. Wherein, the addition amount of Pd (dba) is 1mol% of M2.
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chloro-benzoate, 100mmol of 3-pyridineboronic acid, 40g of potassium carbonate (300 mmol), 800ml of THF and 200ml of water, and 1mol% of Pd (PPh 3 ) 4 . The reaction was carried out at 65℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain yellow powder M4. Wherein Pd (PPh) 3 ) 4 The amount of (2) bromo-5-chloro-benzoic acid methyl ester added was 1mol%.
M4 (100 mmol,1 eq), glacial acetic acid 200ml,100ml concentrated sulfuric acid were heated to reflux and reacted for 12h. After the reaction, water was added, and the precipitated solid was filtered to obtain intermediate M5.
100mmol of intermediate M5 is dissolved in 500ml of THF, the temperature is reduced to 0 ℃, 220mmol of methyl magnesium chloride is added dropwise, and the temperature is naturally raised after the dropwise addition is completed, and the reaction is carried out for 8 hours. After the reaction, water is added into the reaction liquid, and the organic phase is extracted and concentrated to obtain an intermediate M6.
Into the reaction flask were charged 100mmol of M6, 100mmol of 2 aminobiphenyl, 40g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-tert-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization from xylene to obtain yellow powder M7. Wherein, the addition amount of Pd (dba) is 1mol% of M6.
Into the reaction flask were charged 100mmol of M3, 100mmol of M7, 40g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of Pd (dba), 2mol% of tri-t-butylphosphine. The reaction was carried out at 130℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the mixture was separated, washed with water, and the organic phase was concentrated, and the obtained solid was purified by recrystallization from xylene to obtain yellow powder a17. Wherein, the addition amount of Pd (dba) is 1mol% of M3.
1 H NMR(CDCl3,400MHz)δ8.64(s,1H),8.17(d,J＝7.2Hz,2H),7.95(d,J＝8.0Hz,4H),7.74(s,1H),7.67(d,J＝10.0Hz,2H),7.58-7.50(m,5H),7.48–7.33(m,6H),7.33(d,J＝6.8Hz,2H),7.32–7.07(m,4H),7.11(d,J＝10.0Hz,1H),7.08-7.01(m,2H),1.75(s,6H).
M/Z: theory, 693.85; experimental values, 693.2.
Other compounds of the present application can be synthesized by selecting appropriate starting materials according to the concepts of examples 1-4, and any other appropriate methods and starting materials can be selected for synthesis.
The invention also discloses an organic electroluminescent device which comprises the organic luminescent material.
In the present application, the method of manufacturing the OLED device is not particularly limited, and may be manufactured using any method known in the art.
Application example 1
Ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until water is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;
the above-mentioned anode is provided withIs placed in a vacuum cavity, vacuumized to be less than 10 -5 Vacuum evaporating HT-11 on the anode layer film as a hole injection layer at an evaporation rate of 0.1nm/s and an evaporation film thickness of 10nm;
vacuum evaporating A1 material on the hole injection layer to serve as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 80nm;
vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material GHP-16 and a dye material RPD-1, evaporating by utilizing a multi-source co-evaporation method, adjusting the evaporation rate of the main material GHP-16 to be 0.1nm/s, wherein the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the main material, and the total evaporation film thickness is 30nm;
vacuum evaporating an electron transport layer on the luminescent layer, wherein a material ET-26 is selected as the electron transport material, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples and comparative examples were measured using a digital source meter and a luminance meter at the same luminance, specifically, the luminance of the organic electroluminescent devices was measured to be 5000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the lifetime test of LT95 is as follows: at 5000cd/m using a luminance meter 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 4750cd/m 2 Time in hours.
Application examples 2 to 6
The organic light-emitting materials A4, A9, a17 according to the present invention were used as hole transport materials, respectively, and the rest was the same as in example 1. The test results are shown in Table 1.
Comparative examples of application
HT-28 was used as a hole transporting material, and the rest was the same as in application example 1, and the test results are shown in Table 1.
TABLE 1 organic electroluminescent device Performance results
From the data in the table 1, the novel organic material prepared by the invention is used for hole transport materials of organic electroluminescent devices, can effectively reduce the voltage at take off and landing, improve the current efficiency, prolong the service life of the devices, and is a hole transport material with good performance.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (4)
1. An organic luminescent material, characterized in that the organic luminescent material has a structure shown in the following general formula (I):
wherein Ar is as described 1 Selected from phenyl;
ar as described 2 Selected from any one of the following substituted or unsubstituted: biphenyl, dibenzothienyl, 9-dimethylfluorenyl;
R 1 -R 4 independently of each other selected from hydrogen;
l is selected from a bond;
x is selected from S, NR 7 The method comprises the steps of carrying out a first treatment on the surface of the Y is selected from O, S, CR 5 R 6 、NR 7 ；
R 5 、R 6 Independently selected from C 1 -C 10 An alkyl group; r is R 7 Selected from unsubstituted C 6 An aryl group;
a is selected from formula (II);
Z 1 -Z 8 selected from CR or N, R is selected from hydrogen.
2. An organic luminescent material as claimed in claim 1, wherein the organic luminescent material is selected from any one of the following compounds:
3. an organic electroluminescent device, characterized in that it comprises the organic luminescent material according to any one of claims 1-2.
4. An organic electroluminescent device as claimed in claim 3, characterized in that the organic luminescent material is used as a hole transport material for the organic electroluminescent device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010453418.3A CN111548353B (en) | 2020-05-26 | 2020-05-26 | Organic luminescent material and organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010453418.3A CN111548353B (en) | 2020-05-26 | 2020-05-26 | Organic luminescent material and organic electroluminescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111548353A CN111548353A (en) | 2020-08-18 |
| CN111548353B true CN111548353B (en) | 2023-05-19 |
Family
ID=72000481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010453418.3A Active CN111548353B (en) | 2020-05-26 | 2020-05-26 | Organic luminescent material and organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111548353B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112125873B (en) * | 2020-09-08 | 2023-08-25 | 烟台显华化工科技有限公司 | Compound, hole transport material, organic electroluminescent device and display device |
| CN111978329B (en) * | 2020-09-09 | 2023-04-07 | 烟台显华化工科技有限公司 | Compound, hole transport material, organic electroluminescent device and display device |
| CN112159326A (en) * | 2020-09-21 | 2021-01-01 | 烟台显华化工科技有限公司 | Compound, luminescent layer dye material and organic electroluminescent device |
| CN114335398B (en) * | 2021-11-25 | 2023-07-28 | 陕西莱特迈思光电材料有限公司 | Organic electroluminescent device and electronic device including the same |
| CN114163447B (en) * | 2021-12-08 | 2023-09-19 | 武汉天马微电子有限公司 | Organic compound and electroluminescent application thereof |
| WO2024016249A1 (en) * | 2022-07-21 | 2024-01-25 | 北京大学深圳研究生院 | Organic host material and light-emitting device |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110446714A (en) * | 2017-03-16 | 2019-11-12 | 德山金属株式会社 | Compound for organic electronic element, the organic electronic element and its electronic equipment using the compound |
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
| CN110734446A (en) * | 2019-10-30 | 2020-01-31 | 烟台显华化工科技有限公司 | organic compound and application thereof |
| CN110776513A (en) * | 2019-11-29 | 2020-02-11 | 烟台显华化工科技有限公司 | Organic compound and application thereof |
| CN111004241A (en) * | 2019-12-27 | 2020-04-14 | 烟台显华化工科技有限公司 | Organic compound and application thereof |
| CN111187273A (en) * | 2020-02-26 | 2020-05-22 | 烟台显华化工科技有限公司 | Organic compound and application thereof |
-
2020
- 2020-05-26 CN CN202010453418.3A patent/CN111548353B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110446714A (en) * | 2017-03-16 | 2019-11-12 | 德山金属株式会社 | Compound for organic electronic element, the organic electronic element and its electronic equipment using the compound |
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
| CN110734446A (en) * | 2019-10-30 | 2020-01-31 | 烟台显华化工科技有限公司 | organic compound and application thereof |
| CN110776513A (en) * | 2019-11-29 | 2020-02-11 | 烟台显华化工科技有限公司 | Organic compound and application thereof |
| CN111004241A (en) * | 2019-12-27 | 2020-04-14 | 烟台显华化工科技有限公司 | Organic compound and application thereof |
| CN111187273A (en) * | 2020-02-26 | 2020-05-22 | 烟台显华化工科技有限公司 | Organic compound and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111548353A (en) | 2020-08-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111548353B (en) | Organic luminescent material and organic electroluminescent device | |
| CN111635415B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN111269219B (en) | Organic luminescent material and organic electroluminescent device | |
| CN110698458A (en) | Organic luminescent material and application thereof | |
| CN111978329B (en) | Compound, hole transport material, organic electroluminescent device and display device | |
| CN111548354A (en) | Organic light-emitting material and organic electroluminescent device | |
| CN111303134A (en) | Organic light-emitting material and organic electroluminescent device | |
| CN112125892B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN113264911A (en) | Compound, organic light-emitting material and organic electroluminescent device | |
| CN112174918B (en) | Compound, hole transport material, organic electroluminescent device and display device | |
| CN113816898A (en) | Compound, electron transport material, organic electroluminescent device and display device | |
| CN112125873A (en) | Compound, hole transport material, organic electroluminescent device and display device | |
| CN110776513B (en) | Organic compound and application thereof | |
| CN113264871A (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112321521A (en) | Electron transport material, organic electroluminescent device and display device | |
| CN111303187B (en) | Organic luminescent material and organic electroluminescent device | |
| CN112125813A (en) | Compound, hole transport material and organic electroluminescent device | |
| CN111423455A (en) | Bithiophene fused heterocycle organic compound and application thereof | |
| CN113321649B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112110885B (en) | Hole transport material, organic electroluminescent device and display device | |
| CN112028879B (en) | Electron transport material, organic electroluminescent device and display device | |
| CN112125861B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112341470B (en) | Electron transport material, organic electroluminescent device and display device | |
| CN111377942B (en) | Benzo five-membered fused heterocycle organic compound and application thereof | |
| CN115991699A (en) | Naphthalene bridging double-suction fragment compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |