WO2023070987A1 - 有机化合物及包含该有机化合物的有机电致发光器件和电子装置 - Google Patents
有机化合物及包含该有机化合物的有机电致发光器件和电子装置 Download PDFInfo
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- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=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
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000010276 construction Methods 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 125000005956 isoquinolyl group Chemical group 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
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- 238000000206 photolithography Methods 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
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 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
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000825 ultraviolet detection Methods 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
- 238000007740 vapor deposition Methods 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
Images
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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Definitions
- the application belongs to the technical field of organic electroluminescence, and in particular relates to an organic compound and an organic electroluminescent device and electronic device containing the organic compound.
- organic electroluminescent materials have the advantages of ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. It has been widely used in industries such as flat panel display, flexible display, solid state lighting and vehicle display.
- phosphorescent organic electroluminescent devices are the main development direction, and are mainly used in display devices such as mobile phones and vehicles.
- display devices such as mobile phones and vehicles.
- green organic electroluminescent devices there are still problems such as low luminous efficiency and short lifetime, which lead to the degradation of device performance. Therefore, to address the efficiency or lifetime of phosphorescent host materials, it is necessary to continuously develop new materials that are high-efficiency, long-life, and suitable for mass production and can be used in organic electroluminescent devices.
- an organic compound is provided, the structure of the organic compound is as shown in formula 1:
- L is selected from single bonds, substituted or unsubstituted arylene groups with 6-30 carbon atoms;
- Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
- Ar 3 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms;
- n 11 is the number of R 11 , selected from 1, 2 or 3, when n 11 is greater than 1, any two R 11 are the same or different;
- the substituents in L 1 , L 2 , L 3 , Ar 1 , Ar 2 and Ar 3 are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-12 carbon atoms, carbon Aryl groups with 6-12 atoms, trialkylsilyl groups with 3-12 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, and Cycloalkyl with 3-10, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms;
- any two adjacent substituents form a ring.
- the organic compound provided by the present application uses specific 3,3-linked biscarbazole as the mother nucleus, deuterates at least two ortho positions of the biscarbazole linkage, and one of the carbazole rings is connected to an aryl group, The twist angle between the two carbazole rings is reduced, and the conjugation is improved, thereby improving the hole mobility and charge transport balance of the host material. It is applied to the host material of the light-emitting layer of phosphorescent organic electroluminescent devices (especially green organic electroluminescent devices), so that the light-emitting layer has good hole transport characteristics and improves the efficiency of electron and hole recombination to form excitons. Therefore, the device has a reduced voltage, and the luminous efficiency and lifetime characteristics of the device are improved.
- the second aspect of the present application provides an organic electroluminescence device, the organic electroluminescence device comprises an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; wherein the function
- the layer comprises the organic compound of the first aspect.
- a third aspect of the present application provides an electronic device, which includes the organic electroluminescent device described in the second aspect.
- Fig. 1 is a schematic structural view of an organic electroluminescence device according to an embodiment of the present application.
- FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
- L is selected from single bonds, substituted or unsubstituted arylene groups with 6-30 carbon atoms;
- R 11 is selected from hydrogen or deuterium
- n 11 is the number of R 11 , selected from 1, 2 or 3, when n 11 is greater than 1, any two R 11 are the same or different;
- the substituents in L 1 , L 2 , L 3 , Ar 1 , Ar 2 and Ar 3 are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-12 carbon atoms, carbon Aryl groups with 6-12 atoms, trialkylsilyl groups with 3-12 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, and Cycloalkyl with 3-10, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms;
- each q is independently 0, 1, 2 or 3
- each R is independently selected from hydrogen, deuterium, fluorine, chlorine
- its meaning is:
- Formula Q-1 represents that there are q substituents R" on the benzene ring , each R" can be the same or different, and the options of each R" do not affect each other;
- Formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings
- the number q of "substituents may be the same or different, each R" may be the same or different, and the options of each R" do not affect each other.
- Trialkylsilyl group alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, heterocyclic ring with 2-10 carbon atoms Alkyl, alkoxy having 1-10 carbon atoms.
- the "substituted" functional group can be substituted by one or more than two substituents in the above Rc; when two substituents Rc are connected to the same atom, these two substituents Rc can exist independently Or connect to each other to form a spiro ring with the atom; when there is a substituent Rc on two adjacent carbon atoms in the functional group, the adjacent two substituents Rc can exist independently or be fused with the functional group connected synthetic ring.
- two adjacent substituents XX form a ring means that these two substituents can form a ring but not necessarily form a ring, including: the situation where two adjacent substituents form a ring and two A situation where adjacent substituents do not form a ring.
- any two adjacent substituents may include two substituents on the same atom, and may also include Has one substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated ring with the atom connected together; when two adjacent atoms have a substituent respectively When , the two substituents can be fused to form a ring.
- any two adjacent substituents form a ring means that in Ar 1 , Ar 2 or Ar 3 , any two adjacent The substituents in may or may not form a ring.
- the number of carbon atoms in the ring can be 5-13, and the ring can be saturated or unsaturated; the ring is for example: ring Hexane, cyclopentane, adamantane, benzene ring, naphthalene ring, fluorene ring, etc., but not limited thereto.
- the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L is selected from a substituted arylene group with 12 carbon atoms, all the carbon atoms of the arylene group and the substituents thereon are 12.
- Ar 1 is Then its carbon atom number is 7; L is Its carbon number is 12.
- alkyl may include straight chain alkyl or branched chain alkyl.
- the alkyl group may have 1 to 10 carbon atoms, and in the present application, a numerical range such as “1 to 10" refers to each integer in the given range; for example, “an alkyl group of 1 to 10 carbon atoms” refers to Alkyl groups may contain 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Furthermore, an alkyl group may be substituted or unsubstituted.
- the alkyl group is selected from alkyl groups with 1-5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl , tert-butyl and amyl.
- cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including single ring and condensed ring structures.
- the cycloalkyl group may have 3 to 10 carbon atoms, and a numerical range such as "3 to 10" refers to each integer in the given range; for example, "cycloalkyl group of 3 to 10 carbon atoms” refers to a Cycloalkyl groups of 1, 4, 5, 6, 7, 8, 9 or 10 carbon atoms. Cycloalkyl groups can be substituted or unsubstituted. Examples of cycloalkyl groups, such as cyclopentyl, cyclohexane, adamantyl.
- aryl refers to an optional functional group or substituent derived from an aromatic carbocycle.
- the aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group, in other words, the aryl group can be a single-ring aryl group, a condensed ring aryl group, two or more single-ring aryl groups connected by carbon-carbon bond conjugation. Cyclic aryl groups, single-ring aryl groups and condensed-ring aryl groups connected through carbon-carbon bond conjugation, and two or more fused-ring aryl groups connected through carbon-carbon bond conjugation.
- the fused ring aryl group may include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as a phenanthrenyl, a fluorenyl, anthracenyl) and the like.
- the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
- biphenyl, terphenyl, etc. are aryl groups.
- aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, terphenylene, pyrenyl, benzofluoranthenyl , Base etc.
- the arylene group referred to refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
- the substituted aryl group can be that one or more than two hydrogen atoms in the aryl group are replaced by such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, Haloalkyl, cycloalkyl, heterocycloalkyl, alkoxy and other groups are substituted.
- the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group with 18 carbon atoms refers to the aryl group and its The total number of carbon atoms in the substituents is 18.
- heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be B, O, N, P, Si, at least one of Se and S.
- the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system, or a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and any aromatic
- the ring system is an aromatic single ring or an aromatic fused ring.
- heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, Acridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridine Azinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuryl, phen
- thienyl, furyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type
- N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic rings linked by carbon-carbon bonds.
- System type heteroaryl for example, in the present application, the number of carbon atoms of a substituted or unsubstituted heteroaryl group can be 3, 4, 5, 6, 10, 12, 18, 20, 24, 25 1, 28, 29, 30, of course, the number of carbon atoms can also be other numbers, which will not be listed here.
- the heteroarylene referred to refers to a divalent group formed by further loss of a hydrogen atom from the heteroaryl group.
- the substituted heteroaryl group can be one or more than two hydrogen atoms in the heteroaryl group replaced by such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group, etc.
- Substituted by groups such as radicals, haloalkyls, cycloalkyls, heterocycloalkyls, and alkoxy groups. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
- heteroaryl as a substituent in L 1 , L 2 , L 3 , Ar 1 , Ar 2 , and Ar 3 include, but are not limited to: pyridyl, carbazolyl, dibenzofuran base, dibenzothienyl.
- the halogen group may include fluorine, iodine, bromine, chlorine and the like.
- trialkylsilyl group having 3-12 carbon atoms include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
- haloalkyl groups having 1-10 carbon atoms include, but are not limited to, trifluoromethyl.
- a non-positioning linkage refers to a single bond protruding from the ring system It means that one end of the link can be connected to any position in the ring system that the bond runs through, and the other end is connected to the rest of the compound molecule.
- the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two unpositioned linkages that run through the bicyclic ring, and the meanings represented include the formula (f -1)-any possible connection mode shown in formula (f-10).
- the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned link extending from the middle of a benzene ring on one side,
- the meaning represented by it includes any possible connection mode shown in formula (X'-1)-formula (X'-4).
- the organic compound is selected from compounds shown in formula 2:
- L 1 and L 2 are independently selected from single bonds, substituted or unsubstituted arylene groups with 6-30 carbon atoms, and substituted or unsubstituted heteroarylene groups with 3-30 carbon atoms;
- L is selected from single bonds, substituted or unsubstituted arylene groups with 6-30 carbon atoms;
- Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
- Ar 3 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms;
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 are each independently selected from hydrogen or deuterium, and R 2 , R 3 , R 5 and R 6 at least two of which are deuterium;
- the substituents in L 1 , L 2 , L 3 , Ar 1 , Ar 2 and Ar 3 are independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-12 carbon atoms, carbon Aryl groups with 6-12 atoms, trialkylsilyl groups with 3-12 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, and Cycloalkyl with 3-10, heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms;
- any two adjacent substituents form a ring.
- the organic compound is selected from compounds shown in the following formula 2-1-formula 2-6:
- R 11 is deuterium, and n 11 is selected from 1, 2 or 3.
- R 11 is deuterium, and n 11 is selected from 3.
- L 1 and L 2 are independently selected from single bonds, substituted or unsubstituted arylene groups with 6-12 carbon atoms, substituted or unsubstituted arylene groups with 12-18 carbon atoms The heteroarylene.
- the substituents in L 1 and L 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, and phenyl group.
- substituents in L 1 and L 2 include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl.
- L 1 and L 2 are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, Substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofurylene, substituted or unsubstituted dibenzothienylene.
- the substituents in L 1 and L 2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl.
- L 1 and L 2 are independently selected from single bonds, substituted or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of the following groups:
- the substituted group V contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; And when the substituted group V contains multiple substituents, the substituents are the same or different.
- L 1 and L 2 are each independently selected from a single bond or the group consisting of the following groups:
- L 3 is selected from a single bond or a phenylene group.
- L 3 is selected from a single bond or the group consisting of the following groups:
- Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, substituted or unsubstituted heteroarylene groups with 12-20 carbon atoms base.
- the substituents in Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, and alkyl groups with 6-12 carbon atoms.
- Aryl is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, and alkyl groups with 6-12 carbon atoms.
- any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms.
- substituents in Ar include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
- intermediate B-1 (15g, 54.0mmol), iodobenzene (16.53g, 81.0mmol), cuprous iodide (1.03g, 5.4mmol), potassium carbonate ( 18.63g, 135.01mmol), o-phenanthroline (0.54g, 2.7mmol), 18-crown-6 (1.43g, 5.4mmol), DMF (150mL), the temperature was raised to 150°C under stirring, and kept for 16h; then Cool the reaction mixture to room temperature, add ethyl acetate (200mL) and deionized water (200mL), stir for 15 minutes, separate the organic phase, add anhydrous magnesium sulfate to dry, remove the solvent under reduced pressure; Purify by silica gel column chromatography with methane/n-heptane as mobile phase to obtain intermediate C-1 (12.4 g; 65%).
- intermediate B-X in the following table 3 replaces intermediate B-1
- raw material 2 replaces iodobenzene
- intermediate C-1 (10g, 28.26mmol), intermediate F-1 (8.72g, 29.67mmol), palladium acetate (0.06g, 0.28mmol), X- Phos (0.27g, 0.56mmol), potassium carbonate (7.81g, 56.52mmol), toluene (80mL), ethanol (40mL), deionized water (20mL), heated to 75-80°C under stirring conditions, kept for 8h; then The reaction mixture was lowered to room temperature, added deionized water (200mL), stirred for 15 minutes, separated the organic phase, added anhydrous magnesium sulfate to dry, and removed the solvent under reduced pressure; The phase was purified by silica gel column chromatography to obtain compound 221 (12.03 g; 75%).
- Embodiment 1 green organic electroluminescent device
- Anode preparation the thickness is The ITO substrate was cut into a size of 40mm ⁇ 40mm ⁇ 0.5mm, and the photolithography process was used to obtain the experimental substrate with cathode, anode and insulating layer patterns, and the surface was treated with ultraviolet ozone and O 2 : N 2 plasma to increase the anode Work function and remove scum.
- HIL hole injection layer
- Vacuum-evaporated HT-02 on the hole transport layer to form hole adjustment layer Vacuum-evaporated HT-02 on the hole transport layer to form hole adjustment layer.
- GH-N:compound 221:Ir(mppy) 3 is co-evaporated with a film thickness ratio of 45%:45%:10%, forming a thickness of organic light-emitting layer (G-EML).
- An organic electroluminescent device was fabricated by the same method as in Example 1, except that the compound shown in Table 10 below was used instead of Compound 221 when forming the organic light emitting layer.
- An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound I was used instead of Compound 221 when forming the organic light-emitting layer.
- An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound II was used instead of Compound 221 when forming the organic light-emitting layer.
- An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound III was used instead of Compound 221 when forming the organic light-emitting layer.
Abstract
提供一种有机化合物及包含该有机化合物的有机电致发光器件和电子装置,属于有机电致发光领域。所述有机化合物的结构如式1所示,所述有机化合物应用于有机电致发光器件中,可显著改善有机电致发光器件的性能。
Description
相关申请的交叉引用
本申请要求于2021年10月28日递交的申请号为202111260690.0的中国专利申请,以及2021年12月07日递交的申请号为202111488233.7的中国专利申请的优先权,在此引用上述中国专利申请的内容全文以作为本申请的一部分。
本申请属于有机电致发光技术领域,尤其涉及一种有机化合物及包含该有机化合物的有机电致发光器件和电子装置。
有机电致发光材料(OLED)作为新一代显示技术,具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点,已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
目前,对于绿光有机电致发光器件而言,磷光型有机电致发光器件为主要的发展方向,且主要用于移动电话、车载等显示设备。然而,关于绿色有机电致发光器件,仍然存在发光效率较低和寿命较短等问题,从而导致器件性能下降。因此,针对磷光主体材料的效率或寿命问题,需要不断地开发高效率、长寿命、适于量产的可用于有机电致发光器件的新材料。
需要说明的是,在上述背景技术部分公开的信息仅用于加强对本申请的背景的理解,因此可以包括不构成对本领域普通技术人员已知的现有技术的信息。
发明内容
本申请提供了一种有机化合物及包含其的有机电致发光器件和电子装置,用以解决现有技术的有机电致发光器件发光效率较低和寿命较短的问题。
为实现上述目的,本申请采用如下的技术方案:
根据本申请第一个方面,提供一种有机化合物,该有机化合物的结构如式1所示:
该有机化合物的结构如式1所示:
其中,L
1、L
2分别独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基;
L
3选自单键、碳原子数为6-30的取代或未取代的亚芳基;
Ar
1、Ar
2分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基;
Ar
3选自碳原子数为6-30的取代或未取代的芳基;
R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8、R
9、R
10分别独立地选自氢或氘,且R
2、R
3、R
5和R
6中的至少两个为氘;
R
11选自氢或氘;
n
11为R
11的个数,选自1、2或3,当n
11大于1时,任意两个R
11相同或不同;
所述L
1、L
2、L
3、Ar
1、Ar
2、Ar
3中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-12的杂芳基、碳原子数为6-12的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基;
任选地,在Ar
1、Ar
2、Ar
3中,任意两个相邻的取代基形成环。
本申请提供的有机化合物,使用特定3,3位连接的双咔唑作为母核,在双咔唑连接键的至少两个邻位中进行氘代,且其中一个咔唑环上连接芳基,使得两个咔唑环之间的扭曲角度减小,共轭性提高,从而提升了主体材料的空穴迁移率以及电荷传输平衡性。将其应用于磷光有机电致发光器件的发光层主体材料(尤其是绿色有机电致发光器件),使得发光层具有良好的空穴传输特性,提高了电子和空穴复合形成激子的效率,从而使器件具有降低的电压,改善器件的发光效率和寿命特性。
本申请的第二方面提供一种有机电致发光器件,该有机电致发光器件包括相对设置的阳极和阴极,以及设于所述阳极和所述阴极之间的功能层;其中,所述功能层包含第一方面所述的有机化合物。
本申请的第三方面提供一种电子装置,该电子装置包括第二方面所述的有机电致发光器件。
此处的附图被并入说明书中并构成本说明书的一部分,示出了符合本申请的实施例,并与说明书一起用于解释本申请的原理。
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的电子装置的结构示意图。
附图标记说明
100、阳极;200、阴极;300、功能层;310、空穴注入层;321、空穴传输层;322、空穴辅助层;330、有机发光层;340、空穴阻挡层;350、电子传输层;360、电子注入层;400、电子装置。
现在将参考附图更全面地描述示例实施方式。然而,示例实施方式能够以多种形式实施,且不应被理解为限于在此阐述的范例;相反,提供这些实施方式使得本申请将更加全面和完整,并 将示例实施方式的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中,提供许多具体细节从而给出对本申请的实施方式的充分理解。
所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中,提供许多具体细节从而给出对本申请的实施例的充分理解。然而,本领域技术人员将意识到,可以实践本申请的技术方案而没有所述特定细节中的一个或更多,或者可以采用其它的方法、组元、材料等。在其它情况下,不详细示出或描述公知结构、材料或者操作以避免模糊本申请的主要技术创意。
本申请提供一种有机化合物,该有机化合物的结构如式1所示:
其中,L
1、L
2分别独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基;
L
3选自单键、碳原子数为6-30的取代或未取代的亚芳基;
Ar
1、Ar
2分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基;
Ar
3选自碳原子数为6-30的取代或未取代的芳基;
R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8、R
9、R
10分别独立地选自氢或氘,且R
2、R
3、R
5和R
6中的至少两个为氘;
R
11选自氢或氘;
n
11为R
11的个数,选自1、2或3,当n
11大于1时,任意两个R
11相同或不同;
所述L
1、L
2、L
3、Ar
1、Ar
2、Ar
3中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-12的杂芳基、碳原子数为6-12的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基;
任选地,在Ar
1、Ar
2、Ar
3中,任意两个相邻的取代基形成环。
在本申请中,所采用的描述方式“……各自独立地选自”与“……分别独立地选自”可以互换,均应做广义理解,其既可以是指在不同基团中,相同符号之间所表达的具体选项之间互相不影响,也可以表示在相同的基团中,相同符号之间所表达的具体选项之间互相不影响。例如, “
其中,各q独立地为0、1、2或3,各R”独立地选自氢、氘、氟、氯”,其含义是:式Q-1表示苯环上有q个取代基R”,各个R”可以相同也可以不同,每个R”的选项之间互不影响;式Q-2表示联苯的每一个苯环上有q个取代基R”,两个苯环上的R”取代基的个数q可以相同或不同,各个R”可以相同也可以不同,每个R”的选项之间互不影响。
在本申请中,“取代或未取代的”这样的术语是指,在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述,将取代基统称为Rc)。例如,“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、碳原子数为3-12的杂芳基、碳原子数为6-12的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基。
在本申请中,“取代的”官能团可以被上述Rc中的一个或2个以上的取代基取代;当同一个原子上连接有两个取代基Rc时,这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成螺环;当官能团中两个相邻的碳原子上各存在一个取代基Rc时,相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中,术语“任选”、“任选地”意味着随后所描述的事件可以发生但不必发生,该说明包括该事情发生或者不发生的情况。例如,“任选地,两个相邻取代基××形成环”意味着这两个取代基可以形成环但不是必须形成环,包括:两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。
在本申请中,“任意两个相邻的取代基形成环”中,“任意两个相邻的”可以包括同一个原子上具有两个取代基,还可以包括两个相邻的原子上分别具有一个取代基;其中,当同一个原子上具有两个取代基时,两个取代基可以与其共同连接的原子形成饱和或不饱和的环;当两个相邻的原子上分别具有一个取代基时,这两个取代基可以稠合成环。
在本申请中,“任选地,在Ar
1、Ar
2、Ar
3中,任意两个相邻的取代基形成环”是指在Ar
1、Ar
2或Ar
3中,任意两个相邻的取代基可以形成环,也可以不形成环。举例而言,当Ar
1中相邻的两个取代基成环时,该环的碳原子数可以为5-13,且该环可以是饱和的,也可以是不饱和的;该环例如:环己烷、环戊烷、金刚烷、苯环、萘环、芴环等,但不限于此。
在本申请中,取代或未取代的官能团的碳原子数,指的是所有碳原子数。举例而言,若L选自碳原子数为12的取代的亚芳基,则亚芳基及其上的取代基的所有碳原子数为12。例如:Ar
1为
则其碳原子数为7;L为
其碳原子数为12。
在本申请中,“烷基”可以包括直链烷基或支链烷基。烷基可具有1至10个碳原子,在本申请中,诸如“1至10”的数值范围是指给定范围中的各个整数;例如,“1至10个碳原子的烷基”是指可包含1、2、3、4、5、6、7、8、9或10个碳原子的烷基。此外,烷基可为取代的或未取代的。
可选地,烷基选自碳原子数为1-5的烷基,具体实例包括但不限于,甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基和戊基。
在本申请中,环烷基指的是含有脂环结构的饱和烃,包含单环和稠环结构。环烷基可具有3-10个碳原子,诸如“3至10”的数值范围是指给定范围中的各个整数;例如,“3至10个碳原子的环烷基”是指可包含3个、4个、5个、6个、7个、8个、9个或10个碳原子的环烷基。环烷基可为取代的或未取代的。环烷基的实例,如环戊烷基、环己烷基、金刚烷基。
在本申请中,芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基,换言之,芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即,除非另有说明,通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中,稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。举例而言,在本申请中,联苯基、三联苯基等为芳基。芳基的实例可以包括但不限于,苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、三亚苯基、芘基、苯并荧蒽基、
基等。
本申请中,“取代或未取代的芳基”可含有6-30个碳原子,在一些实施方式中,取代或未取代的芳基中的碳原子数是6-25个,在另一些实施方式中,取代或未取代的芳基中的碳原子数是6-20个,在另一些实施方式中,取代或未取代的芳基中的碳原子数是6-18个,在又一些实施方式中,取代或未取代的芳基中的碳原子数是6-12个。举例而言,本申请中,取代或未取代的芳基的碳原子数量可以是6个、12个、13个、14个、15个、18个、20个、24个、25个、28个、29个、30个,当然,碳原子数还可以是其他数量,在此不再一一列举。在本申请中,联苯基可以理解为苯基取代的芳基,也可以理解为未取代的芳基。
本申请中,涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中,取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、卤代烷基、环烷基、杂环烷基、烷氧基等基团取代。应当理解地是,取代的芳基的碳原子数,指的是芳基和芳基上的取代基的碳原子总数,例如碳原子数为18的取代的芳基,指的是芳基及其取代基的总碳原子数为18。
在本申请中,L
1、L
2、L
3、Ar
1、Ar
2、Ar
3中作为取代基的芳基,其具体实例包括但不限于:苯基、萘基、蒽基、菲基、二甲基芴基、联苯基等等。
在本申请中,杂芳基是指环中包含1、2、3、4、5或6个杂原子的一价芳香环或其衍生物,杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基,换言之,杂芳基可以是单个芳香环体系,也可以是通过碳碳键共轭连接的多个芳香环体系,且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地,杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等,而不限于此。其中,噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基,N-苯基咔唑基、N-吡啶基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。举例而言,本申请中,取代或未取代的杂芳基的碳原子数量可以是3个、4个、5个、6个、10个、12个、18个、20个、24个、25个、28个、29个、30个,当然,碳原子数还可以是其他数量,在此不再一一列举。
本申请中,涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
在本申请中,取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、卤代烷基、环烷基、杂环烷基、烷氧基等基团取代。应当理解的是,取代的杂芳基的碳原子数,指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中,L
1、L
2、L
3、Ar
1、Ar
2、Ar
3中作为取代基的杂芳基,其具体实例包括但不限于:吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基。
在本申请中,卤素基团可以包括氟、碘、溴、氯等。
在本申请中,碳原子数为3-12的三烷基硅基的具体实例包括但不限于,三甲基硅基、三乙基硅基等。
在本申请中,碳原子数为1-10的卤代烷基的具体实例包括但不限于,三氟甲基。
举例而言,如下式(f)中所示地,式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接,其所表示的含义,包括如式(f-1)-式(f-10)所示出的任一可能的连接方式。
再举例而言,如下式(X')中所示地,式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接,其所表示的含义,包括如式(X'-1)-式(X'-4)所示出的任一可能的连接方式。
下文中对于不定位连接或不定位取代的含义与此处相同,后续将不再进行赘述。
在本申请一些实施方式中,所述有机化合物选自式2所示的化合物:
其中,L
1、L
2分别独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基;
L
3选自单键、碳原子数为6-30的取代或未取代的亚芳基;
Ar
1、Ar
2分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基;
Ar
3选自碳原子数为6-30的取代或未取代的芳基;
R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8、R
9、R
10分别独立地选自氢或氘,且R
2、R
3、R
5和R
6中的至少两个为氘;
所述L
1、L
2、L
3、Ar
1、Ar
2、Ar
3中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-12的杂芳基、碳原子数为6-12的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基;
任选地,在Ar
1、Ar
2、Ar
3中,任意两个相邻的取代基形成环。
在本申请一些实施方式中,所述有机化合物选自如下式2-1-式2-6所示的化合物:
其中,在式2-4至2-6中,R
11为氘,n
11选自1、2或3。
优选地,在式2-4至2-6中,R
11为氘,n
11选自3。
在本申请一些实施方式中,L
1、L
2分别独立地选自单键、碳原子数为6-12的取代或未取代的亚芳基、碳原子数的12-18的取代或未取代的亚杂芳基。
可选地,L
1、L
2中的取代基相同或不同,分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、苯基。
具体地,L
1、L
2中的取代基具体实例包括但不限于:氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基。
在本申请另一些实施方式中,L
1、L
2分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基。
可选地,L
1、L
2中的取代基相同或不同,分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基。
在本申请一些实施方式中,L
1、L
2分别独立地选自单键、取代或未取代的基团V,其中,未取代的基团V选自如下基团组成的组:
可选地,L
1、L
2分别独立地选自单键或者如下基团组成的组:
在本申请一些实施方式中,L
3选自单键或亚苯基。
在本申请一些实施方式中,L
3选自单键或如下基团组成的组:
在本申请一些实施方式中,Ar
1、Ar
2分别独立地选自碳原子数为6-25的取代或未取代的芳基、碳原子数为12-20的取代或未取代的亚杂芳基。
可选地,Ar
1、Ar
2中的取代基相同或不同,分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基。
任选地,在Ar
1、Ar
2中,任意两个相邻的取代基形成碳原子数为5-13的饱和或不饱和环。
具体地,Ar
1、Ar
2中的取代基的具体实例包括但不限于:氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基。
在本申请另一些实施方式中,Ar
1、Ar
2分别独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基。
可选地,Ar
1、Ar
2中的取代基相同或不同,分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
任选地,在Ar
1、Ar
2中,任意两个相邻的取代基形成芴环。
在本申请一些实施方式中,Ar
1、Ar
2分别独立地选自取代或未取代的基团W,其中,未取代的基团W选自以下基团组成的组:
可选地,Ar
1、Ar
2分别独立地选自如下基团组成的组:
在本申请一些实施方式中,Ar
3为碳原子数为6-20的取代或未取代的芳基。
可选地,Ar
3为碳原子数为6-15的取代或未取代的芳基。
可选地,Ar
3为碳原子数为6-12的取代或未取代的芳基。
可选地,Ar
3中的取代基相同或不同,分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、苯基。
具体地,Ar
3中的取代基的具体实例包括但不限于:氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基。
在本申请另一些实施方式中,Ar
3选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基。
可选地,Ar
3中的取代基相同或不同,分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基。
在本申请一些实施方式中,Ar
3选自如下基团组成的组:
在本申请一些实施方式中,R
1、R
2、R
3均为氘或者R
4、R
5、R
6均为氘。
当本申请有机化合物的R
1、R
2、R
3均为氘或者R
4、R
5、R
6均为氘时,有机化合物用于有机电致发光器件的主体材料时,器件性能得到明显改善。
在本申请一些实施方式中,R
4、R
5、R
6、R
7、R
8、R
9、R
10均为氘。
在本申请一些具体的实施方式中,当本申请有机化合物的R
4、R
5、R
6、R
7、R
8、R
9、R
10均为氘时,器件具备更低的工作电压、更高的发光效率和更长的使用寿命。
可选地,所述有机化合物选自如下化合物组成的组:
本申请还提供一种有机电致发光器件,该有机电致发光器件包括相对设置的阳极和阴极,以及介于阳极与阴极之间的至少一层功能层,该功能层包含本申请的有机化合物。
进一步地,所述功能层包括有机发光层,所述有机发光层包含所述有机化合物。
在本申请的一种具体实施方式中,所述有机电致发光器件为绿色磷光有机电致发光器件。
在本申请的一种具体实施方式中,如图1所示,本申请的有机电致发光器件包括阳极100、阴极200、以及介于阳极层与阴极层之间的至少一层功能层300。该功能层300可以包括层叠设置的空穴注入层310、空穴传输层321、空穴辅助层322、有机发光层330、电子传输层350以及电子注入层360。其中,有机发光层330可以含有本申请第一方面所述的有机化合物。
可选地,阳极100包括以下阳极材料,其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数,work function)材料。阳极材料具体实例包括:金属如镍、铂、钒、铬、铜、锌和金 或它们的合金;金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);组合的金属和氧化物如ZnO:Al或SnO
2:Sb;或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺,但不限于此。优选包括包含氧化铟锡(铟锡氧化物,indium tin oxide)(ITO)作为阳极的透明电极。
可选地,空穴传输层321可以包括一种或者多种空穴传输材料,空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物,本申请对此不做特殊的限定。举例而言,在本申请的一种实施方式中,空穴传输层321由HT-01组成。
可选地,空穴辅助层322可以包括一种或者多种空穴传输材料,空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物,本申请对此不做特殊的限定。举例而言,在本申请的一种实施方式中,空穴辅助层322由HT-02组成。
可选地,有机发光层330可以由单一发光材料组成,也可以包括主体材料和客体材料。可选地,有机发光层330由主体材料和客体材料组成,注入有机发光层330的空穴和电子可以在有机发光层330复合而形成激子,激子将能量传递给主体材料,主体材料将能量传递给客体材料,进而使得客体材料能够发光。
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料,本申请对此不做特殊的限制。
在本申请的一种更具体的实施方式中,所述有机电致发光器件为绿色有机电致发光器件,有机发光层330包含本申请所述的有机化合物、GH-N和客体材料Ir(mppy)
3。
电子传输层350可以为单层结构,也可以为多层结构,其可以包括一种或者多种电子传输材料,电子传输材料可以选自苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料,本申请对此不做特殊的限定。举例而言,电子传输层350可以由ET-01和LiQ组成。
可选地,在有机发光层330和电子传输层350之间可以设置或不设置空穴阻挡层340。空穴阻挡层可以包括一种或多种空穴阻挡材料,本申请对此不做特殊的限定。
可选地,阴极200包括以下阴极材料,其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括:金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、铅或它们的合金;或多层材料如LiF/Al,Liq/Al,LiO
2/Al,LiF/Ca,LiF/Al和BaF
2/Ca,但不限于此。优选包括包含银和镁的金属电极作为阴极。
可选地,在阳极100和空穴传输层321之间还可以设置有空穴注入层310,以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料,本申请对此不做特殊的限制。在本申请的一种实施方式中,空穴注入层310可以由F4-TCNQ组成。
可选地,在阴极200和电子传输层350之间还可以设置有电子注入层360,以增强向电子传输层350注入电子的能力。电子注入层360可以包括有碱金属硫化物、碱金属卤化物等无机材料,或者可以包括碱金属与有机物的络合物。在本申请的一种实施方式中,电子注入层360可以包括镱(Yb)。
本申请还提供一种电子装置,该电子装置包括本申请所述的有机电致发光器件。
举例而言,如图2所示,本申请提供的电子装置为电子装置400,其包括上述有机电致发光器件。该电子装置可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置,例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。由于电子装置400具有上述有机电致发光器件,因此具有相同的有益效果,本申请在此不再赘述。
下面将结合实施例详细描述本申请,但是,以下描述是用于解释本申请,而不是以任意方式限制本申请的范围。实施例只列举部分化合物的合成过程,其他化合物也可以按照类似的反应步骤获得。
合成实施例
下面所描述的合成例中,除非另有声明,否则所有的温度单位为摄氏度。部分试剂购买于商品供应商如Aldrich Chemical Company,Arco Chemical Company and Alfa Chemical Company,部分不能直接采购的中间体是通过商购原料经简单反应制备得到,除非另有声明,否则使用时都没有经过进一步纯化。其余的常规试剂从天津好寓宇化学品有限公司、天津市福晨化学试剂厂、武汉鑫华远科技发展有限公司、青岛腾龙化学试剂有限公司和青岛海洋化工厂等处购买得到。各合成例中的反应一般是在氮气或氩气正压下进行的,或者在无水溶剂上套一干燥管(除非另有声明);在反应中,反应瓶都塞上合适的橡皮塞,底物通过注射器注入反应瓶中。所用到的各个玻璃器皿都是干燥过的。
在纯化时,色谱柱是硅胶柱,硅胶(100-200目)购于青岛海洋化工厂。
在各个合成例中,低分辨率质谱(MS)数据的测定条件是:Agilent 6120四级杆HPLC-M(柱子型号:Zorbax SB-C18,2.1×30mm,3.5微米,6min,流速为0.6mL/min。流动相:5%-95%(含0.1%甲酸的乙腈)在(含0.1%甲酸的水)中的比例),采用电喷雾电离(ESI),在210nm/254nm下,用UV检测。
核磁共振氢谱:布鲁克(Bruker)400MHz核磁仪,室温条件下,以CD
2Cl
2为溶剂(以ppm为单位),用TMS(0ppm)作为参照标准。
中间体K-1的合成:
将1,3-二氯苯-D4(30.0g,198.65mmol)放入四口烧瓶中,控制温度为25摄氏度,将发烟硝酸(13.77g,218.51mmol)和浓硫酸(19.48g,198.65mmol)依次滴入,滴加完毕,静置分层,分离有机相,加入无水硫酸镁干燥后,减压除去溶剂,得到中间体K-1(30.99g;80%)。
中间体S-1的合成:
向干燥并经过氮气置换的500mL圆底烧瓶中,加入S-A(30g,146.41mmol),S-B(18.59g,146.41mmol),四(三苯基膦)钯(8.45g,7.32mmol),四丁基溴化铵(2.36g,7.32mmol),碳酸钾(30.35g,219.62mmol),甲苯(240mL),乙醇(120mL),去离子水(60mL),搅拌条件下升温至75-80℃,保持8h;而后将反应混合物降至室温,加入去离子水(200mL),搅拌15分钟,分离有机相,加入无水硫酸镁干燥后,减压除去溶剂;将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯,得到中间体S-1(9.1.g;30%)。
中间体A-1的合成:
向干燥并经过氮气置换的500mL圆底烧瓶中,加入2,4-二氯硝基苯(30g,156.26mmol),2-联苯硼酸(34.04g,171.88mmol),四(三苯基膦)钯(3.6g,3.12mmol),四丁基溴化铵(1.00g,3.13mmol),碳酸钾(64.79g,468.77mmol),甲苯(240mL),乙醇(120mL),去离子水(60mL),搅拌条件下升温至75-80℃,保持8h;而后将反应混合物降至室温,加入去离子水(200mL),搅拌15分钟,分离有机相,加入无水硫酸镁干燥后,减压除去溶剂;将所得粗产品使用1:6二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯,得到中间体A-1(33.87g;70%)。
参照中间体A-1的合成方法,以下表1中原料1代替2,4-二氯硝基苯,SM-X替代2-联苯硼酸,合成下表1中的中间体A-X:
表1
中间体B-1的合成
向干燥并经过氮气置换的圆底烧瓶中,加入中间体A-1(30g,96.85mmol),三苯基膦(63.51g,242.14mmol),邻二氯苯(300mL),搅拌条件下升温至170℃,保持18h;而后将反应混合物降至室温,常压蒸馏除去邻二氯苯,加入甲苯(200mL),搅拌15分钟,后减压除去溶剂;将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯,得到中间体B-1(13.45g;50%)。
参照中间体B-1合成方法,以中间体A-X代替中间体A-1合成下表2中的中间体B-X:
表2
中间体C-1的合成
向干燥并经过氮气置换的圆底烧瓶中,加入中间体B-1(15g,54.0mmol),碘苯(16.53g,81.0mmol),碘化亚铜(1.03g,5.4mmol),碳酸钾(18.63g,135.01mmol),邻菲罗啉(0.54g,2.7mmol),18-冠醚-6(1.43g,5.4mmol),DMF(150mL),搅拌条件下升温至150℃,保持16h;而后将反应混合物降至室温,加入乙酸乙酯(200mL)和去离子水(200mL),搅拌15分钟,分离有机相,加入无水硫酸镁干燥后,减压除去溶剂;将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯,得到中间体C-1(12.4g;65%)。
参照中间体C-1的合成方法,以下表3中的中间体B-X代替中间体B-1,原料2替代碘苯,合成下表3中的中间体C-X:
表3
中间体CM-1的合成
向干燥并经过氮气置换的圆底烧瓶中,加入中间体C-24(20g,56.04mmol),联硼酸频哪醇酯(21.35g,84.06mmol),三(二亚苄基丙酮)二钯(1.54g,1.68mmol),醋酸钾(11.00g,112.09mmol),2-二环己基磷-2’,4,’6’-三异丙基联苯(1.60g,3.36mmol),1,4-二氧六环(200mL),搅拌条件下升温至100℃,保持16h;而后将反应混合物降至室温,加入乙酸乙酯(200mL)和去离子水(200mL),搅拌15分钟,分离有机相,加入无水硫酸镁干燥后,减压除去溶剂;将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯,得到CM-1(17.6g;70%)。
参照CM-1的合成方法,以下表4中中间体C-25代替中间体C-24,合成下表4中的中间体CM-2:
表4
中间体D-1的合成
向干燥并经过氮气置换的圆底烧瓶中,加入氘代咔唑(20g,114.12mmol),N-溴代丁二酰亚胺(NBS)(50.78g,285.29mmol),DMF(200mL),搅拌条件下室温搅拌,保持16h;而后向反应混合物中加入乙酸乙酯(200mL)和去离子水(200mL),分离有机相,加入无水硫酸镁干燥后,减压除去溶剂,得到中间体D-1(12.42g;43%)。
中间体E-1的合成
向干燥并经过氮气置换的圆底烧瓶中,加入中间体D-1(10g,39.50mmol),碘苯(12.08g,59.25mmol),碘化亚铜(0.75g,3.95mmol),碳酸钾(13.65g,98.76mmol),邻菲罗啉(0.39g,1.98mmol),18-冠醚-6(1.04g,3.95mmol),DMF(100mL),搅拌条件下升温至150℃,保持16h;而后将反应混合物降至室温,加入乙酸乙酯(200mL)和去离子水(200mL),搅拌15分钟,分离有机相,加入无水硫酸镁干燥后,减压除去溶剂;将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯,得到中间体E-1(6.89g;53%)。
参照中间体E-1的合成方法,以下表中原料3替代碘苯,合成下表5中的中间体E-X:
表5
中间体F-1的合成
将中间体E-1(10g,30.37mmol)加入盛有THF(100ml)的三口瓶中,-80℃下滴加正丁基锂(2.07g,31.89mmol),滴加完后保温1h后滴加硼酸三甲酯(4.73g,45.56mmol),继续保温1h后升温至室温搅 拌过夜。加入盐酸(2mol/L)调节pH至中性,后过滤得白色粗品,用正庚烷打浆得中间体F-1(5.36g,收率60%)。
参照中间体F-1的合成方法,以下表6中原料4替代E-1,合成下表6中的中间体F-X:
表6
化合物221的合成
向干燥并经过氮气置换的圆底烧瓶中,加入中间体C-1(10g,28.26mmol),中间体F-1(8.72g,29.67mmol),醋酸钯(0.06g,0.28mmol),X-Phos(0.27g,0.56mmol),碳酸钾(7.81g,56.52mmol),甲苯(80mL),乙醇(40mL),去离子水(20mL),搅拌条件下升温至75-80℃,保持8h;而后将反应混合物降至室温,加入去离子水(200mL),搅拌15分钟,分离有机相,加入无水硫酸镁干燥后,减压除去溶剂;将所得粗产品使用二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯,得到化合物221(12.03g;75%)。
参照化合物221的合成的方法,以下表7中原料C替代中间体C-1,原料F替代中间体F-1,合成下表7中的化合物:
表7
对以上合成化合物进行质谱分析,得到数据如下表8所示:
表8
化合物编号 | 质谱([M+H] +) | 化合物编号 | 质谱([M+H] +) |
221 | 568.3 | 223 | 644.3 |
237 | 720.3 | 243 | 720.3 |
244 | 720.2 | 249 | 734.3 |
253 | 750.3 | 257 | 796.3 |
268 | 720.4 | 269 | 720.3 |
270 | 734.3 | 276 | 750.3 |
285 | 796.4 | 290 | 720.3 |
291 | 720.3 | 345 | 796.4 |
352 | 796.4 | 349 | 796.4 |
325 | 734.3 | 337 | 750.3 |
74 | 644.3 | 99 | 720.3 |
120 | 720.3 | 133 | 644.3 |
169 | 644.3 | 197 | 796.4 |
213 | 750.3 | 22 | 720.3 |
40 | 720.3 | 54 | 734.3 |
354 | 640.3 | 365 | 640.3 |
374 | 640.4 | 378 | 640.2 |
397 | 640.2 | 408 | 640.3 |
413 | 640.3 | 444 | 720.3 |
462 | 796.4 | 470 | 796.4 |
480 | 720.3 | 482 | 796.3 |
483 | 796.3 | 486 | 796.5 |
488 | 720.2 | 489 | 796.2 |
490 | 796.4 | 543 | 700.3 |
544 | 662.3 | 545 | 669.3 |
546 | 723.3 | 547 | 748.3 |
548 | 750.3 | 549 | 885.3 |
556 | 648.3 | 558 | 645.3 |
559 | 649.3 |
部分化合物的核磁数据如下表9所示
表9
有机电致发光器件制备及评估
实施例1绿色有机电致发光器件
阳极制备:将厚度为
的ITO基板切割成40mm×40mm×0.5mm的尺寸,采用光刻工序,得到具有阴极、阳极以及绝缘层图案的实验基板,利用紫外臭氧以及O
2:N
2等离子进行表面处理,以增加阳极的功函数和清除浮渣。
将ET-01和LiQ以1:1的膜厚比进行蒸镀形成了
厚的电子传输层(ETL),将Yb蒸镀在电子传输层上以形成厚度为
的电子注入层(EIL),然后将镁(Mg)和银(Ag)以1:9的膜厚比在电子注入层上真空蒸镀,形成厚度为
的阴极。
实施例2-57
除了在形成有机发光层时,以下表10中所示的化合物替代化合物221以外,利用与实施例1相同的方法制作有机电致发光器件。
比较例1
除了在形成有机发光层时,以化合物Ⅰ替代化合物221以外,利用与实施例1相同的方法制作有机电致发光器件。
比较例2
除了在形成有机发光层时,以化合物Ⅱ替代化合物221以外,利用与实施例1相同的方法制作有机电致发光器件。
比较例3
除了在形成有机发光层时,以化合物Ⅲ替代化合物221以外,利用与实施例1相同的方法制作有机电致发光器件。
以上实施例1-57和比较例1-3使用的材料结构如下所示:
对如上制得的有机电致发光器件,在15mA/cm
2的条件下分析了器件的性能,其结果示于下表10所示:
表10
根据上表10所示的数据可知,与比较例1-3相比,本申请化合物,用作绿色有机电致发光器件的有机发光层主体时,器件性能得到了明显改善。本申请有机化合物,相比于比较例1-3,寿命至少提高了12.3%,电流效率至少提高了12.1%。
本申请提供的有机化合物,使用特定3,3位连接的双咔唑作为母核,在双咔唑连接键的至少两个邻位中进行氘代,且其中一个咔唑环上连接芳基,双咔唑上连接供电子基团,这样特定的组合,使得两个咔唑环之间的扭曲角度减小,共轭性提高,从而提升了主体材料的空穴迁移率以及电荷传输平衡性。将其应用于磷光有机电致发光器件的发光层主体材料中的空穴型主体材料(尤其是绿色有机电致发光器件),使得发光层具有良好的空穴传输特性,提高了电子和空穴复合形成激子的效率,从而使器件具有降低的电压,改善器件的发光效率和寿命特性。
本领域技术人员在考虑说明书及实践这里公开的发明后,将容易想到本申请的其它实施方案。本申请旨在涵盖本申请的任何变型、用途或者适应性变化,这些变型、用途或者适应性变化遵循本申请的一般性原理并包括本申请未公开的本技术领域中的公知常识或惯用技术手段。说明书和实施例仅被视为示例性的,本申请的真正范围和精神由下面的权利要求书指出。
应当理解的是,本申请并不局限于上面已经描述并在附图中示出的精确结构,并且可以在不脱离其范围进行各种修改和改变。本申请的范围仅由所附的权利要求书来限制。
Claims (15)
- 一种有机化合物,其特征在于,该有机化合物的结构如式1所示:其中,L 1、L 2分别独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基;L 3选自单键、碳原子数为6-30的取代或未取代的亚芳基;Ar 1、Ar 2分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基;Ar 3选自碳原子数为6-30的取代或未取代的芳基;R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9、R 10分别独立地选自氢或氘,且R 2、R 3、R 5和R 6中的至少两个为氘;R 11选自氢或氘;n 11为R 11的个数,选自1、2或3,当n 11大于1时,任意两个R 11相同或不同;所述L 1、L 2、L 3、Ar 1、Ar 2、Ar 3中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-12的杂芳基、碳原子数为6-12的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基;任选地,在Ar 1、Ar 2、Ar 3中,任意两个相邻的取代基形成环。
- 根据权利要求1所述的有机化合物,其特征在于,所述有机化合物的结构如式2所示:其中,L 1、L 2分别独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基;L 3选自单键、碳原子数为6-30的取代或未取代的亚芳基;Ar 1、Ar 2分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基;Ar 3选自碳原子数为6-30的取代或未取代的芳基;R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9、R 10分别独立地选自氢或氘,且R 2、R 3、R 5和R 6中的至少两个为氘;所述L 1、L 2、L 3、Ar 1、Ar 2、Ar 3中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为3-12的杂芳基、碳原子数为6-12的芳基、碳原子数为3-12的三烷基硅基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为2-10的杂环烷基、碳原子数为1-10的烷氧基;任选地,在Ar 1、Ar 2、Ar 3中,任意两个相邻的取代基形成环。
- 根据权利要求1或2所述的有机化合物,其特征在于,L 1、L 2分别独立地选自单键、碳原子数为6-12的取代或未取代的亚芳基、碳原子数的12-18的取代或未取代的亚杂芳基;优选地,L 1、L 2中的取代基相同或不同,分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、苯基。
- 根据权利要求1或2所述的有机化合物,其特征在于,L 1、L 2分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基;优选地,L 1、L 2中的取代基相同或不同,分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基。
- 根据权利要求1或2所述的有机化合物,其特征在于,L 3选自单键或亚苯基。
- 根据权利要求1或2所述的有机化合物,其特征在于,Ar 1、Ar 2分别独立地选自碳原子数为6-25取代或未取代的芳基、碳原子数为12-20取代或未取代的亚杂芳基;优选地,Ar 1、Ar 2中的取代基相同或不同,分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基;任选地,在Ar 1、Ar 2中,任意两个相邻的取代基形成碳原子数为5-13的饱和或不饱和环。
- 根据权利要求1或2所述的有机化合物,其特征在于,Ar 1、Ar 2分别独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基;优选地,Ar 1、Ar 2中的取代基相同或不同,分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基;任选地,在Ar 1、Ar 2中任意两个相邻的取代基形成芴环。
- 根据权利要求1或2所述的有机化合物,其特征在于,Ar 3为碳原子数为6-20的取代或未取代的芳基;优选地,Ar 3中的取代基相同或不同,分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、苯基。
- 根据权利要求1或2所述的有机化合物,其特征在于,Ar 3选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基;优选地,Ar 3中的取代基相同或不同,分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基。
- 根据权利要求1或2所述的有机化合物,其特征在于,R 1、R 2、R 3均为氘或者R 4、R 5、R 6均为氘。
- 根据权利要求1或2所述的有机化合物,其特征在于,R 4、R 5、R 6、R 7、R 8、R 9、R 10均为氘。
- 一种有机电致发光器件,包括相对设置的阳极和阴极,以及设于所述阳极和所述阴极之间的功能层;所述功能层包含权利要求1-13中任意一项所述的有机化合物;优选地,所述功能层包含有机发光层;优选地,所述有机电致发光器件为绿色有机电致发光器件。
- 一种电子装置,其特征在于,包括权利要求14所述的有机电致发光器件。
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