CN117683046A - Organic compound, organic electroluminescent device and electronic apparatus - Google Patents
Organic compound, organic electroluminescent device and electronic apparatus Download PDFInfo
- Publication number
- CN117683046A CN117683046A CN202211006817.0A CN202211006817A CN117683046A CN 117683046 A CN117683046 A CN 117683046A CN 202211006817 A CN202211006817 A CN 202211006817A CN 117683046 A CN117683046 A CN 117683046A
- Authority
- CN
- China
- Prior art keywords
- substituted
- group
- carbon atoms
- unsubstituted
- groups
- 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.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 103
- 239000010410 layer Substances 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 48
- -1 cyano, methyl Chemical group 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 229910052805 deuterium Inorganic materials 0.000 claims description 33
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 239000002346 layers by function Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 5
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005649 substituted arylene group Chemical group 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 42
- 239000000463 material Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000376 reactant Substances 0.000 description 17
- 230000005525 hole transport Effects 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 239000012043 crude product Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 125000000355 1,3-benzoxazolyl group Chemical class O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- DLXBGTIGAIESIG-UHFFFAOYSA-N 1,8-dibromonaphthalene Chemical compound C1=CC(Br)=C2C(Br)=CC=CC2=C1 DLXBGTIGAIESIG-UHFFFAOYSA-N 0.000 description 2
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 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 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 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
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 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 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
- C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
-
- 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
- H10K85/626—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present application relates to an organic compound, an organic electroluminescent device, and an electronic apparatus. The organic compound has the formula 1The organic compound is applied to the organic electroluminescent device, so that the performance of the device can be improved remarkably.
Description
Technical Field
The present disclosure relates to the field of organic compounds, and more particularly, to an organic compound, and an organic electroluminescent device and an electronic device including the same.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. An organic electroluminescent device (OLED) generally includes a cathode and an anode disposed opposite each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of a plurality of organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transporting layer, an electron transporting layer, and the like. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards. Singlet excitons and triplet excitons are generated at a ratio of 1:3 according to the statistical theorem of electron spin. The limit of the internal quantum efficiency of the fluorescent light-emitting organic electroluminescent device using light emission using singlet excitons is 25%. On the other hand, it is known that in a phosphorescent organic electroluminescent device using light emission using triplet excitons, when intersystem crossing (intersystem crossing) is efficiently performed from the singlet excitons, the internal quantum efficiency can be improved to 100%.
However, at present, there are many problems with phosphorescent materials in terms of organic electroluminescent materials. For example: short service life and low efficiency. Therefore, it is necessary to develop new materials to improve the performance of electronic components.
The above information disclosed in the background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not form the prior art that is already known to a person of ordinary skill in the art.
Disclosure of Invention
In order to solve the above problems, an object of the present application is to provide an organic compound, which can improve the performance of an organic electroluminescent device and an electronic apparatus, for example, reduce the driving voltage of the device, and increase the efficiency and lifetime of the device, and an organic electroluminescent device and an electronic apparatus including the organic compound.
According to a first aspect of the present application, there is provided an organic compound having a structure as shown in formula 1:
wherein X is selected from C (R 4 R 5 ) O, S or N (Ar);
R 1 selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or groups represented by formula 2;
ar is substituted with 1, 2, 3, 4 or 5R 6 Substituted arylene groups having 6 to 30 carbon atoms;
Each R is 6 The two groups are the same or different and are respectively and independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups with 1-10 carbon atoms, aryl groups with 6-30 carbon atoms or groups shown in a formula 2;
R 2 and R is 3 The same or different, are respectively and independently selected from hydrogen, deuterium, cyano, halogen groups, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms or groups shown in a formula 2;
and said R is 1 、R 6 、R 2 And R is 3 One or two of the groups represented by formula 2;
R 4 and R is 5 The same or different, are respectively and independently selected from alkyl with 1-10 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
the R is 1 、R 2 、R 3 、R 4 、R 5 、L、L 1 、L 2 、Ar 1 And Ar is a group 2 The substituents in the two are the same or different and are respectively independent Is selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, cycloalkyl with 3-20 carbon atoms, heteroaryl with 3-20 carbon atoms, deuterated aryl with 6-20 carbon atoms, halogenated aryl with 6-20 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, halogenated alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound.
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.
The core group of the organic compound is formed by fusing dibenzo five-membered rings and benzoxazoles in a specific mode, and the core group has a planar ring-like structure which can keep a higher first triplet energy level value and has strong carrier transmission capability and high energy transfer capability; meanwhile, the group has good electron dispersing capability. The core group is combined with triarylamine, and the formed compound can effectively improve the electron tolerance of molecules when the molecules are used as hole transport materials. When the organic compound is used as a main material of a luminescent layer in a red organic electroluminescent device, the device performance can be remarkably improved.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
320. Hole transport layer 320, first hole transport layer 330, second hole transport layer 340, and organic light emitting layer
350. Electron transport layer 360, electron injection layer 400, and electronic device
Detailed Description
In view of the foregoing problems of the prior art, it is an object of the present invention to provide an organic compound, which can improve the performance of an organic electroluminescent device and an electronic apparatus, for example, reduce the driving voltage of the device, and increase the efficiency and lifetime of the device, and an organic electroluminescent device and an electronic apparatus including the same.
According to a first aspect of the present application, there is provided an organic compound having a structure as shown in formula 1:
wherein X is selected from C (R 4 R 5 ) O, S or N (Ar);
R 1 selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or groups represented by formula 2;
ar is substituted with 1, 2, 3, 4 or 5R 6 Substituted arylene groups having 6 to 30 carbon atoms;
each R is 6 The two groups are the same or different and are respectively and independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups with 1-10 carbon atoms, aryl groups with 6-30 carbon atoms or groups shown in a formula 2;
R 2 and R is 3 The same or different, are each independently selected from hydrogen, deuterium, cyano, halogen groups, substituted or unsubstituted aryl groups having 6 to 30 carbon atomsA group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a group represented by formula 2;
and said R is 1 、R 6 、R 2 And R is 3 One or two of the groups represented by formula 2;
R 4 and R is 5 The same or different, are respectively and independently selected from alkyl with 1-10 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 And Ar is a group 2 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
the R is 1 、R 2 、R 3 、R 4 、R 5 、L、L 1 、L 2 、Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-20 carbon atoms, heteroaryl group with 3-20 carbon atoms, deuterated aryl group with 6-20 carbon atoms, halogenated aryl group with 6-20 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, triarylsilyl group with 18-24 carbon atoms, halogenated alkyl group with 1-10 carbon atoms and deuterated alkyl group with 1-10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In the present application, "any two adjacent substituents form a ring," any two adjacent "may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring. For example, when Ar 1 With 2 or more substituents, and any adjacent substituent forms a ring, a saturated or unsaturated cyclic group is formed, for example: benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, cyclopentane, cyclohexane, adamantane, and the like.
In the present application, the fluorenyl group may be substituted with 1 or 2 substituents, wherein, in the case where the above fluorenyl group is substituted, it may be:and the like, but is not limited thereto.
In this application, the descriptions "each … … is independently" and "… … is independently" and "… … is independently selected from" may be interchanged, and should be understood in a broad sense, which refers to that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, " Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R', and the two benzene rings are onThe number q of R ' substituents of the (E) can be the same or different, and each R ' can be the same or different, so that options of each R ' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, alkyl, cycloalkyl, heteroaryl, deuterated aryl, halogenated aryl, trialkylsilyl, triarylsilyl, haloalkyl, deuterated alkyl, etc.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
Aryl in this application refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,Radicals, spirobifluorenyl radicals, and the like. In the present application, reference to arylene means aryl The step of losing a divalent or polyvalent group formed by one or more hydrogen atoms.
In the present application, terphenyl includes
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
Heteroaryl in this application refers to a monovalent aromatic ring or derivative thereof containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds. In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, or the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, the substituted or unsubstituted aryl group may have 6 to 25 carbon atoms, and for example, the carbon atoms may have 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25.
Specific examples of the aryl group as a substituent in the present application include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl,A base.
In the present application, the substituted or unsubstituted heteroaryl group may have 12 to 20 carbon atoms, for example, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to, triazinyl, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl, carbazolyl, N-phenylcarbazolyl.
In the present application, the non-positive connection is referred to as a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X ') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formulas (X-1) to (X ' -4).
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
Specific examples of triarylsilyl groups in this application include, but are not limited to, triphenylsilyl groups.
In the present application, the cycloalkyl group having 3 to 20 carbon atoms may have 3, 4, 5, 6, 7, 8, or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
In the present application, R 1 、R 6 、R 2 And R is 3 And only one of them is a group represented by formula 2.
In the present application, the organic compound is selected from compounds represented by formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, formula 1-9, formula 1-10, formula 1-11, formula 1-12, or formula 1-13:
in some embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms;
optionally, the substituents in L are the same or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms or phenyl groups.
In other embodiments of the present application, L is selected from a single bond, phenylene, naphthylene, or biphenylene.
In some embodiments of the present application, L is selected from the group consisting of a single bond or:
Specifically, L is selected from the group consisting of a single bond or:
in some embodiments of the present application, L is selected from the group consisting of a single bond or:
optionally, L is selected from the group consisting of a single bond or:
in some embodiments of the present application, L 1 And L 2 The same or different are independently selected from single bond and carbon atom numberA substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.
Optionally, the L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms or phenyl group.
In other embodiments of the present application, L 1 And L 2 The same or different are respectively and independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuranylene and substituted or unsubstituted dibenzothiophene.
Optionally, the L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, L 1 And L 2 The same or different, are each independently selected from a single bond, a substituted or unsubstituted group V, the unsubstituted group V being selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; and when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
Specifically, L 1 And L 2 The same or different, each independently selected from the group consisting of a single bond or:
in some embodiments of the present application, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Optionally, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, cycloalkyl groups with 1-10 carbon atoms, triphenylsilyl groups or phenyl groups;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a fluorene ring
In other embodiments of the present application, ar 1 And Ar is a group 2 The same or different, are each independently selected from the group consisting of substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted spirobifluorenyl.
Optionally, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexenyl, adamantyl, phenyl, naphthyl or triphenylsilyl.
In some embodiments of the present application, ar 1 And Ar is a group 2 The same or different are each independently selected from the group consisting of substituted or unsubstituted groups V, wherein the unsubstituted groups W are selected from the group consisting of:
the substituted group W has one or more than two substituents, each substituent is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, adamantyl, phenyl, naphthyl or triphenylsilyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different.
Alternatively, ar 1 And Ar is a group 2 The same or different, each independently selected from the group consisting of:
specifically, ar 1 And Ar is a group 2 The same or different, each independently selected from the group consisting of:
in some embodiments of the present application,each independently selected from the group consisting of: />
In some embodiments of the present application,selected from the group consisting of:
in some embodiments of the present application, R 4 And R is 5 Are all methyl groups.
In some embodiments of the present application, R 1 Selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a group represented by formula 2.
Alternatively, R 1 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application Ar is substituted with 1, 2, 3, 4 or 5R 6 Substituted phenylene or naphthylene;
each R is 6 The same or different, are respectively and independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl, phenyl, naphthyl, biphenyl or a group shown in a formula 2;
in some embodiments of the present application, R 2 And R is 3 Identical toOr different, are each independently selected from hydrogen or a group represented by formula 2.
In some embodiments of the present application, R 1 Selected from the group represented by formula 2 or the group consisting of:
in some embodiments of the present application, ar is selected from the group consisting of:
in some embodiments of the present application, R 1 Selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a group represented by formula 2;
ar is substituted with 1, 2, 3, 4 or 5R 6 Substituted phenylene or naphthylene;
each R is 6 The same or different, are respectively and independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl, phenyl, naphthyl, biphenyl or a group shown in a formula 2;
R 2 and R is 3 The same or different are respectively and independently selected from hydrogen or a group shown in a formula 2;
and said R is 1 、R 6 、R 2 And R is 3 And only one of them is a group represented by formula 2.
Optionally, the R 1 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, R 1 Selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a group represented by formula 2;
The R is 1 The substituents in (a) are the same or different and are each independently selected fromDeuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
Ar is substituted with 1, 2, 3, 4 or 5R 6 Substituted phenylene or naphthylene.
Each R is 6 The same or different, are each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, or a group represented by formula 2.
R 2 Selected from hydrogen or a group represented by formula 2.
R 3 Selected from hydrogen or a group represented by formula 2.
In some preferred embodiments of the present application, X is O or S;
R 1 selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a group represented by formula 2;
R 2 and R is 3 The same or different are respectively and independently selected from hydrogen or a group shown in a formula 2;
the R is 1 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl;
R 1 、R 2 and R is 3 And only one of them is a group represented by formula 2.
In some embodiments of the present application, the organic material is selected from the group consisting of compounds as set forth in claim 12.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound of the present application.
In some embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 320, a second hole transport layer 330, an organic light emitting layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are sequentially stacked.
Alternatively, the anode 100 includes an anode material that is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO: al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. A transparent electrode including Indium Tin Oxide (ITO) as an anode is preferable.
Alternatively, the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art will be able to select from the prior art, and this application is not particularly limited. In some embodiments of the present application, first hole transport layer 320 is HT-20 and second hole transport layer 330 is HT-21.
Optionally, a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
in some embodiments of the present application, hole injection layer 310 is comprised of F4-TCNQ and HT-20.
Alternatively, the organic light emitting layer 340 may be composed of a single light emitting layer material, and may also include a host material and a dopant material. Alternatively, the organic light emitting layer 340 is composed of a host material and a dopant material, and holes injected into the organic light emitting layer 340 and electrons injected into the organic light emitting layer 340 may be recombined at the organic light emitting layer 340 to form excitons, which transfer energy to the host material, which transfers energy to the dopant material, thereby enabling the dopant material to emit light.
The host material of the organic light emitting layer 340 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application.
In one embodiment of the present application, the organic light emitting layer 340 comprises the organic material of the present application.
Alternatively, the organic material of the present application is used as a host material (hole-type host material) of the organic light emitting layer 340.
In some embodiments of the present application, the electron-type host material of the organic light emitting layer 340 is
The guest material of the organic light emitting layer 340 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in this application. Guest materials are also known as doping materials or dopants. Specific examples of red phosphorescent dopants for red organic electroluminescent devices include but are not limited to,
in a more specific embodiment, the host material of the organic light emitting layer 340 is an organic compound and RH-01 of the present application, and the guest material is RD-01.
The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from but not limited to ET-01, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in comparison. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:
In some embodiments of the present application, electron transport layer 350 is comprised of ET-01 and LiQ.
In this application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
In some embodiments of the present application, the electron injection layer 360 may include ytterbium (Yb).
A third aspect of the present application provides an electronic device comprising an electronic component as described in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, an electronic device 400 is provided, which includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthetic method of the organic compound of the present application is specifically described below with reference to synthetic examples, but the present application is not limited thereto.
All compounds of the synthetic methods not mentioned in the present application are commercially available starting products.
The synthetic method of the organic material provided in the present application is not particularly limited, and a person skilled in the art can determine a suitable synthetic method according to the preparation method provided in the organic material combination preparation example section of the present application. All organic materials provided herein can be obtained by one skilled in the art from these exemplary preparation methods, and all specific preparation methods for preparing the organic materials are not described in detail herein, and should not be construed as limiting the present application.
Preparation of the Compounds
Synthesis of intermediate b 1:
intermediate a1 (16.1 g;63.4 mmol), 1, 8-dibromonaphthalene (18.1 g;63.4 mmol), tetrakis triphenylphosphine palladium (1.5 g;1.3 mmol), potassium carbonate (17.5 g;126.7 mmol), tetrabutylammonium bromide (4.1 g;12.7 mmol), toluene (120 mL), ethanol (30 mL) and deionized water (30 mL) were added to a nitrogen-protected round bottom flask, warmed to 75-80℃and reacted with stirring for 24 hours. Cooling the reaction solution to room temperature, adding deionized water (200 mL), separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane solvent system to give intermediate b1 (15.5 g; yield 73%) as a pale yellow oil
Referring to the synthesis of intermediate B1, the following intermediate shown in table 1 was synthesized with reactant a instead of intermediate a1 and reactant B instead of 1, 8-dibromonaphthalene:
TABLE 1
Synthesis of intermediate c 1:
intermediate b1 (15.5 g;46.5 mmol), palladium acetate (1.0 g;4.6 mmol), 3-nitropyridine (0.6 g;4.6 mmol), hexafluorobenzene (60 mL), 1, 3-dimethyl-2-imidazolidinone (50 mL) and tert-butyl peroxybenzoate (18.0 g;92.9 mmol) were added to a nitrogen-protected round bottom flask and the reaction was allowed to proceed for 12 hours at 90℃to 95 ℃. Stopping the reaction, cooling to room temperature, adding dichloromethane (100 mL) and deionized water (200 mL) into the reaction solution, separating the solution, washing the organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a solvent to give intermediate c1 (8.0 g; yield 52%) as a white solid.
Referring to the method for the synthesis of intermediate C1, the intermediate shown in table 2 below was synthesized with reactant C instead of intermediate b 1:
TABLE 2
Synthesis of intermediate c 7:
intermediate b7 (15.0 g;41.4 mmol), triphenylphosphine (27.1 g;103.4 mmol) and o-dichlorobenzene (150 mL) were added to a nitrogen-protected round-bottomed flask and reacted for 48 hours with stirring at a temperature of 175℃to 180 ℃. Cooling the reaction solution to room temperature, adding deionized water (200 mL), separating, washing an organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under the conditions of high temperature and reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane system to give intermediate c6 (9.2 g; yield 67%) as a white solid.
Referring to the synthesis of intermediate c7, replacing intermediate b7 with reactant E, the intermediates shown in table 3 below were synthesized:
TABLE 3 Table 3
Synthesis of intermediate c 12:
intermediate b12 (9.0 g;25.7 mmol), palladium chloride (0.2 g;1.3 mmol) and dimethyl sulfoxide (90 mL) were added to a nitrogen-protected round-bottomed flask and reacted for 36 hours at 140℃to 145℃with stirring; cooling to room temperature, adding dichloromethane (100 mL) and deionized water (150 mL) into the reaction solution, separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane to give intermediate c12 (6.6 g; yield 74%) as a white solid
Referring to the synthesis of intermediate c12, substituting reactant G for intermediate b12, the intermediates shown in table 4 below were synthesized:
TABLE 4 Table 4
Synthesis of intermediate c 16:
intermediate b16 (15.8 g;41.0 mmol) and dichloroethane (140 mL) were added to a nitrogen-protected round-bottomed flask, and a solution of trimethylaluminum (14.8 g;204.9 mmol) in hexane was slowly added dropwise with stirring at 20℃to 25℃and the reaction was continued for 1 hour at 20℃to 25℃after the dropwise addition was completed; aqueous hydrochloric acid (22.4 g;614.6 mmol) was added to the reaction mixture, extraction was performed using diethyl ether, the organic phases were combined, dried, and the solvent was removed under reduced pressure; purification of the crude product by silica gel chromatography using dichloromethane/n-heptane as solvent system afforded intermediate c16 (7.2 g; yield 49%) as a white solid.
Referring to the synthesis of intermediate c16, substituting reactant I for intermediate b15, the intermediates shown in table 5 below were synthesized:
TABLE 5
Synthesis of intermediate d 1:
intermediate c1 (7.9 g;23.8 mol), cuprous iodide (0.5 g;2.4 mmol), 8-hydroxyquinaldine (0.8 g;4.8 mmol), tetrabutylammonium hydroxide (18.5 g;71.5 mmol), dimethyl sulfoxide (80 mL) and deionized water (120 mL) were added to a nitrogen-protected round-bottomed flask, and the mixture was allowed to react for 24 hours while stirring at a temperature of 125℃to 130 ℃; cooling to room temperature, adding dichloromethane (150 mL) and deionized water (200 mL) into the reaction solution, separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product obtained was purified by silica gel column chromatography using methylene chloride/n-heptane system to give intermediate d1 (5.1 g; yield 80%) as a white solid
Referring to the synthesis of intermediate d1, substituting reactant L for intermediate c1, the intermediates shown in table 6 below were synthesized:
TABLE 6
Synthesis of intermediate e 1:
intermediate d1 (5.0 g;18.6 mmol), nickel nitrate hexahydrate (5.4 g;18.6 mmol), p-toluenesulfonic acid (0.04 g;0.2 mmol) and acetone (100 mL) were added to a nitrogen protected round bottom flask and reacted for 2 hours under stirring at 20℃to 25 ℃; stopping the reaction, adding dichloromethane (100 mL) and deionized water (150 mL) into the reaction solution, separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product obtained was purified by silica gel column chromatography using methylene chloride/n-heptane system to give intermediate e1 (4.7 g; yield 81%) as a white solid
Referring to the synthesis of intermediate e1, the following intermediate shown in table 7 was synthesized with reactant M instead of intermediate d 1:
TABLE 7
Synthesis of intermediate o 1-cl:
intermediate e1 (4.7 g;15.0 mmol), benzyl alcohol (1.9 g,18.0 mmol), 1' -bis (diphenylphosphino) ferrocene (0.2 g;0.4 mmol) and xylene (50 mL) were added to a nitrogen-protected round-bottomed flask, heated to 130℃to 135℃with stirring, and reacted under reflux for 48h; cooling to room temperature, adding toluene (50 mL) and deionized water (100 mL) to the reaction solution, combining the organic phases, drying the organic layer over anhydrous magnesium sulfate, filtering, and concentrating; purification of the crude product by silica gel column chromatography using methylene chloride/n-heptane yielded intermediate o1-cl as a white solid (3.5 g; yield 63%).
Referring to the synthesis of intermediates o1-cl, the following intermediates shown in Table 8 were synthesized with reactant N instead of intermediate e1 and reactant P instead of benzyl alcohol:
TABLE 8
Synthesis of intermediate n1-cl
Intermediate n1-h (5.5 g;14.9 mmol), iodobenzene (3.3 g;16.4 mmol), cuprous iodide (0.6 g;3.0 mmol), anhydrous potassium carbonate (4.5 g;32.8 mmol), 1, 10-phenanthroline (1.1 g;6.0 mmol), 18-crown-6 (0.8 g;3.0 mmol) and dimethylformamide (50 mL) were added to a nitrogen-protected round-bottomed flask and allowed to warm to 135℃to 140℃with stirring for 24 hours; stopping the reaction, cooling the reaction solution to room temperature, adding deionized water (100 mL) and dichloromethane (100 mL), separating the solution, washing the organic phase with a large amount of water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product obtained was purified by silica gel column chromatography using a dichloromethane/n-heptane solvent system, followed by recrystallization purification using a dichloromethane/n-heptane mixed solvent to give intermediate n1-cl (5.1 g; yield 77%)
Referring to the synthesis of intermediate n1-cl, the following intermediate shown in Table 9 was synthesized by substituting reactant Q for intermediate n1-h and reactant R for iodobenzene:
TABLE 9
Synthesis of intermediate o 1-bo:
intermediate o1-cl (3.5 g;9.5 mmol), pinacol biborate (3.6 g;14.2 mmol), tris (dibenzylideneacetone) dipalladium (0.2 g;0.2 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.2 g;0.4 mmol), potassium acetate (1.4 g;14.2 mmol) and 1, 4-dioxane (30 mL) were added to a nitrogen-protected round bottom flask and reacted at 100℃to 105℃for 24 hours with stirring; cooling to room temperature, adding dichloromethane (50 mL) and deionized water (50 mL) into the reaction solution, separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a solvent to give intermediate o1-bo (3.1 g; yield 71%) as a white solid.
Referring to the synthesis of intermediate o1-bo, the following intermediate shown in Table 10 was synthesized with reactant U in place of intermediate o 1-cl:
table 10
Synthesis of intermediate o 1-ph:
intermediate o1-bo (3.1 g;6.7 mmol), 1-bromo-4-chlorobenzene (1.4 g;7.1 mmol), tetrakis triphenylphosphine palladium (0.2 g;0.1 mmol), potassium carbonate (1.9 g;13.4 mmol), tetrabutylammonium bromide (0.4 g;1.3 mmol), toluene (25 mL), ethanol (6 mL) and deionized water (6 mL) were added to a nitrogen-protected round bottom flask, warmed to 75℃to 80℃and reacted with stirring for 48 hours; cooling the reaction solution to room temperature, adding deionized water (50 mL), separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using a dichloromethane/n-heptane solvent system to give intermediate o1-ph (2.5 g; yield 83%)
Referring to the same procedure as for intermediate o1-ph, substituting reactant V for intermediate o1-bo and reactant W for 1-bromo-4-chlorobenzene, the intermediates shown in Table 11 below were synthesized:
TABLE 11
Synthesis of compound A2:
intermediate o1-cl (5.0 g;13.5 mmol), N-phenyl-2-naphthylamine (3.1 g;14.2 mmol), tris (dibenzylideneacetone) dipalladium (0.1 g;0.1 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.1 g;0.3 mmol), sodium t-butoxide (1.9 g;20.3 mmol) and toluene (50 mL) were added to a nitrogen-protected round bottom flask, heated to 100℃to 105℃and reacted with stirring for 16 hours; cooling the reaction solution to room temperature, adding deionized water (100 mL), separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane solvent system, followed by recrystallization purification using toluene/n-heptane solvent system to give compound A2 (5.5 g; yield 74%) as a white solid.
Referring to the same procedure for compound A2, the following compounds shown in table 12 were synthesized with reactant Y instead of intermediate o1-cl and reactant Z instead of N-phenyl-2-naphthylamine:
table 12
Mass spectrum data for some compounds are shown in table 13 below:
TABLE 13
| Compound A2 | m/z＝553.2(M+H) + | Compound B33 | m/z＝818.3(M+H) + |
| Compound A7 | m/z＝579.2(M+H) + | Compounds of formula (I)B46 | m/z＝758.2(M+H) + |
| Compound A14 | m/z＝679.2(M+H) + | Compound B55 | m/z＝770.3(M+H) + |
| Compound A20 | m/z＝709.2(M+H) + | Compound C1 | m/z＝671.2(M+H) + |
| Compound A39 | m/z＝744.3(M+H) + | Compound C9 | m/z＝735.2(M+H) + |
| Compound A46 | m/z＝653.2(M+H) + | Compound C18 | m/z＝745.2(M+H) + |
| Compound A52 | m/z＝609.2(M+H) + | Compound C48 | m/z＝721.2(M+H) + |
| Compound B8 | m/z＝846.3(M+H) + | Compound D7 | m/z＝757.3(M+H) + |
| Compound B14 | m/z＝743.3(M+H) + | Compound D21 | m/z＝757.3(M+H) + |
| Compound B21 | m/z＝654.3(M+H) + | Compound D32 | m/z＝781.3(M+H) + |
| Compound A61 | m/z＝512.2(M+H) + | Compound A62 | m/z＝741.3(M+H) + |
| Compound A63 | m/z＝744.3(M+H) + | Compound A64 | m/z＝745.3(M+H) + |
The nuclear magnetic data of some compounds are shown in table 14 below:
TABLE 14
Preparation of organic electroluminescent device
Example 1: preparation of red organic electroluminescent device
The anode pretreatment is carried out by the following steps: at a thickness ofThe degree is in turnOn the ITO/Ag/ITO substrate, ultraviolet ozone and O are used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent is used for cleaning the surface of the ITO/Ag/ITO substrate to remove impurities and greasy dirt on the surface of the substrate.
F4-TCNQ and HT-20 were co-evaporated on a test substrate (anode) at a deposition rate ratio of 1% to 99% to give a film having a thickness ofIs then vacuum evaporated onto the Hole Injection Layer (HIL) to form HT-20 with a thickness of +.>Is provided.
Vacuum evaporating compound HT-21 on the first hole transport layer to form a film having a thickness ofIs provided.
Then, on the second hole transport layer, RH-01 compound A2 RD-01 was co-evaporated at a deposition rate ratio of 49% to 2%, to form a film having a thickness ofAn organic light emitting layer (EML).
On the organic light-emitting layer, mixing and evaporating the compounds ET-01 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Electron Injection Layer (EIL) of (a), then steaming magnesium (Mg) and silver (Ag) at a ratio of 1:9Plating rate mixing, vacuum evaporating on electron injection layer to form a film with a thickness of +.>Is provided.
Further, CP-1 is vacuum deposited on the cathode to form a cathode having a thickness ofThereby completing the fabrication of the red organic electroluminescent device.
Examples 2 to 24
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound in table 15 below (collectively referred to as "compound X") was used instead of the compound A2 in example 1 when the light-emitting layer was fabricated.
Comparative examples 1 and 2
An organic electroluminescent device was prepared by the same method as in example 1, except that compound i and compound ii were used in place of compound A2 in example 1, respectively, in the preparation of a light-emitting layer.
Wherein, in preparing each example and comparative example, the main compound used has the following structure:
the red organic electroluminescent devices prepared in examples 1 to 24 and comparative examples 1 to 2 were subjected to performance test, specifically at 10mA/cm 2 IVL performance of the device under the condition of (1) and lifetime of the T95 device at 20mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 15.
TABLE 15
As is clear from table 15 above, examples 1 to 24, in which the compounds of the present application were used as the hole-type host materials in the red light-emitting layer mixed host material, were significantly improved in device voltage, current efficiency and lifetime as compared with comparative examples 1 and 2. Specifically, the current efficiency is improved by at least 15.1%, and the life T95 (h) is improved by at least 12.2%
The core group of the organic compound is formed by fusing dibenzo five-membered rings and benzoxazoles in a specific mode, and the core group is of a ring-like structure with flatness, and can have strong carrier transmission capability and high energy transfer capability while keeping a higher first triplet level value of a material; meanwhile, the group has good electron dispersing capability. The core group is combined with triarylamine, and the formed compound can effectively improve the electron tolerance of molecules when the molecules are used as hole transport materials. When the organic compound is used as a main material of a luminescent layer in a red organic electroluminescent device, the device performance can be remarkably improved. In particular, when the dibenzofive-membered ring is dibenzofuran/dibenzothiophene, the device performance is optimal.
It is to be understood that the present application is not limited to the precise arrangements and instrumentalities shown in the drawings, which have been described above, and that various modifications and changes may be effected without departing from the scope thereof. The scope of the application is limited only by the appended claims.
Claims (14)
1. An organic compound, characterized in that the organic compound has a structure as shown in formula 1:
wherein X is selected from C (R 4 R 5 ) O, S or N (Ar);
R 1 selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or groups represented by formula 2;
ar is substituted with 1, 2, 3, 4 or 5R 6 Substituted arylene groups having 6 to 30 carbon atoms;
each R is 6 The two groups are the same or different and are respectively and independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups with 1-10 carbon atoms, aryl groups with 6-30 carbon atoms or groups shown in a formula 2;
R 2 and R is 3 The same or different, are respectively and independently selected from hydrogen, deuterium, cyano, halogen groups, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms or groups shown in a formula 2;
and said R is 1 、R 6 、R 2 And R is 3 One or two of the groups represented by formula 2;
R 4 and R is 5 The same or different, are respectively and independently selected from alkyl with 1-10 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L、L 1 And L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
the R is 1 、R 2 、R 3 、R 4 、R 5 、L、L 1 、L 2 、Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-20 carbon atoms, heteroaryl group with 3-20 carbon atoms, deuterated aryl group with 6-20 carbon atoms and carbon atomsA halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a ring.
2. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of compounds represented by formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, formula 1-8, formula 1-9, formula 1-10, formula 1-11, formula 1-12, and formula 1-13:
3. The organic compound according to claim 1, wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms;
preferably, the substituents in L are the same or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, or phenyl groups.
4. The organic compound according to claim 1, wherein L is selected from a single bond, phenylene, naphthylene, or biphenylene.
5. The organic compound according to claim 1, wherein L is selected from the group consisting of a single bond or:
6. the organic compound according to claim 1, wherein L 1 And L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-12 carbon atoms and substituted or unsubstituted heteroaryl with 12-18 carbon atoms;
preferably, the L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms or phenyl group.
7. The organic compound according to claim 1, wherein L 1 And L 2 The same or different is respectively and independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophene;
Preferably, the L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
8. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroarylene with 12-20 carbon atoms;
preferably, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, cycloalkyl groups with 1-10 carbon atoms, triphenylsilyl groups or phenyl groups;
optionally in Ar 1 And Ar is a group 2 Any two adjacent substituents form a fluorene ring.
9. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different, are each independently selected from substituted or unsubstituted terphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted spirobifluorenyl;
Preferably, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexenyl, adamantyl, phenyl, naphthyl or triphenylsilyl.
10. The organic compound according to claim 1, wherein R 4 And R is 5 Are all methyl groups.
11. The organic compound according to claim 1, wherein R 1 Selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a group represented by formula 2;
ar is substituted with 1, 2, 3, 4 or 5R 6 Substituted phenylene or naphthylene;
each R is 6 The same or different, are respectively and independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl, phenyl, naphthyl, biphenyl or a group shown in a formula 2;
R 2 and R is 3 The same or different are respectively and independently selected from hydrogen or a group shown in a formula 2;
and said R is 1 、R 6 、R 2 And R is 3 Wherein only one of them is a group represented by formula 2;
preferably, said R 1 The substituents in (a) are the same or different and are each independently selected from deuterium and fluorineCyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
12. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
13. the organic electroluminescent device is characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode;
the functional layer contains the organic compound according to any one of claims 1 to 12;
preferably, the functional layer comprises an organic light emitting layer; the organic light-emitting layer contains the organic compound;
preferably, the organic electroluminescent device is a red organic electroluminescent device.
14. An electronic device comprising the organic electroluminescent device as claimed in claim 13.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211006817.0A CN117683046A (en) | 2022-08-22 | 2022-08-22 | Organic compound, organic electroluminescent device and electronic apparatus |
| KR1020247019602A KR20240103027A (en) | 2022-08-22 | 2023-06-01 | Organic compounds, organic electroluminescent devices and electronic devices |
| PCT/CN2023/097885 WO2024041079A1 (en) | 2022-08-22 | 2023-06-01 | Organic compound, organic electroluminescent device, and electronic apparatus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211006817.0A CN117683046A (en) | 2022-08-22 | 2022-08-22 | Organic compound, organic electroluminescent device and electronic apparatus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117683046A true CN117683046A (en) | 2024-03-12 |
Family
ID=90012333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211006817.0A Pending CN117683046A (en) | 2022-08-22 | 2022-08-22 | Organic compound, organic electroluminescent device and electronic apparatus |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20240103027A (en) |
| CN (1) | CN117683046A (en) |
| WO (1) | WO2024041079A1 (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7166357B2 (en) * | 2003-03-20 | 2007-01-23 | Transitions Optical, Inc. | Photochromic articles that activate behind ultraviolet radiation blocking transparencies and methods for preparation |
| KR101571591B1 (en) * | 2012-12-10 | 2015-11-24 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| KR102198515B1 (en) * | 2014-12-23 | 2021-01-05 | 솔루스첨단소재 주식회사 | Organic light-emitting compound and organic electroluminescent device comprising the same |
| CN114075215B (en) * | 2021-06-10 | 2023-07-14 | 陕西莱特迈思光电材料有限公司 | Organic compound, organic electroluminescent device comprising same and electronic device |
-
2022
- 2022-08-22 CN CN202211006817.0A patent/CN117683046A/en active Pending
-
2023
- 2023-06-01 WO PCT/CN2023/097885 patent/WO2024041079A1/en active Application Filing
- 2023-06-01 KR KR1020247019602A patent/KR20240103027A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20240103027A (en) | 2024-07-03 |
| WO2024041079A1 (en) | 2024-02-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114133332B (en) | Organic compound, electronic component, and electronic device | |
| CN113233987B (en) | Nitrogen-containing compound, electronic element comprising same and electronic device | |
| CN114075176B (en) | Nitrogen-containing compound, organic electroluminescent device and electronic device | |
| CN115368294B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN115385898A (en) | Nitrogen-containing compound, organic electroluminescent device, and electronic device | |
| CN115521214B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN114133351B (en) | Nitrogen-containing compound, and electronic component and electronic device comprising same | |
| WO2023202198A1 (en) | Organic material, electronic element, and electronic apparatus | |
| CN115490601B (en) | Organic compound, electronic component, and electronic device | |
| CN116444384A (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN116478115A (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN113896720B (en) | Organic compound, electronic component, and electronic device | |
| CN116396277A (en) | Organic compound, organic electroluminescent device and electronic device | |
| CN117417260A (en) | Organic material, organic electroluminescent device and electronic device | |
| CN115490602B (en) | Organic compound, electronic element using same and electronic device | |
| CN117683047B (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN117683046A (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN114075214B (en) | Organic compound, organic electroluminescent device and electronic device comprising the same | |
| CN117510480B (en) | Organic compound, organic electroluminescent device and electronic device | |
| CN114230472B (en) | Organic compound, electronic component and electronic device comprising the same | |
| CN115490603B (en) | Organic compound, and electronic component and electronic device including the same | |
| WO2023185039A1 (en) | Organic compound, and electronic element and electronic apparatus comprising same | |
| CN117903075A (en) | Organic compound, organic electroluminescent device and electronic device | |
| CN117430568A (en) | Organic compound, electronic component, and electronic device | |
| CN117946132A (en) | Organic compound, organic electroluminescent device and electronic device |
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 |