WO2018099432A1 - Composé cyclique fusionné, son procédé de préparation et son application - Google Patents

Composé cyclique fusionné, son procédé de préparation et son application Download PDF

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WO2018099432A1
WO2018099432A1 PCT/CN2017/113943 CN2017113943W WO2018099432A1 WO 2018099432 A1 WO2018099432 A1 WO 2018099432A1 CN 2017113943 W CN2017113943 W CN 2017113943W WO 2018099432 A1 WO2018099432 A1 WO 2018099432A1
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atoms
ring
substituted
organic
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Chinese (zh)
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杨曦
潘君友
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广州华睿光电材料有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/72—Spiro hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
    • 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

Definitions

  • the invention relates to the field of organic electroluminescence technology, in particular to a fused ring compound and a preparation method and application thereof.
  • OLEDs Organic light-emitting diodes
  • Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic matter.
  • An organic electroluminescence device utilizing an organic electroluminescence phenomenon generally has a structure in which a positive electrode and a negative electrode and an organic layer are contained therebetween.
  • the organic layer has a multilayer structure, and each layer contains a different organic substance. Specifically, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like may be included.
  • Such an organic electroluminescence device when a voltage is applied between the two electrodes, a hole is injected from the positive electrode into the organic layer, and a negative electrode is injected into the organic substance, and when the injected hole meets the electron, an exciton is formed. The excitons emit light when they transition back to the ground state.
  • Such an organic electroluminescence device has characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.
  • the development of a blue fluorescent material having a narrow-band emission spectrum and good stability is advantageous for obtaining a longer-life and higher-efficiency blue light device, and on the other hand, it is advantageous for the improvement of the color gamut, thereby improving the display effect.
  • the light-emitting layer of the prior art blue organic electroluminescent device adopts a host-guest doping structure.
  • the conventional blue light host material is a ruthenium-based fused ring derivative, as described in the patents CN1914293B, CN102448945B, US2015287928A1, etc.
  • these compounds have problems of insufficient luminous efficiency and brightness, and poor lifetime of the device.
  • an aryl vinylamine compound (WO 04/013073, WO 04/016575, WO 04/018587) can be used.
  • these compounds have poor thermal stability and are easily decomposed, resulting in poor lifetime of the device, which is currently the most important shortcoming in the industry.
  • the blue light-emitting materials can have deep blue light emission, and they are thermally stable, exhibit good efficiency and longevity in the organic electroluminescence element, are easy to repeat in the manufacture and operation of the device, and have simple material synthesis.
  • the present invention provides a fused ring compound of the formula (I):
  • X 1 is CR 1 R 2 , O, S, NR 3 .
  • R 1 , R 2 or R 3 are each independently selected from: H, or a linear alkyl group having 1 to 20 C atoms, or an alkoxy group having 1 to 20 C atoms, or 1 to 20 C. a thioalkoxy group of an atom, or a branched or cyclic alkyl group having 3 to 20 C atoms, or an alkoxy group having 3 to 20 C atoms, or a thio group having 3 to 20 C atoms An alkoxy group, either a substituted or unsubstituted silyl group, or a substituted ketone group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or having 7 to 20 C Aromatic oxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate or isothiocyanate, hydroxy, nitro, CF 3 , Cl, Br,
  • R 1 , R 2 or R 3 groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and/or with a ring to which the group is bonded;
  • At least one of R 11 -R 19 , R 110 , R 111 or R 112 contains a structure as shown in the general formula (III), and the other substituents are each independently selected from: H or a straight having 1 to 20 C atoms.
  • Keto group or alkoxycarbonyl group having 2 to 20 C atoms, or aryloxycarbonyl group having 7 to 20 C atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate , thiocyanate or isothiocyanate, hydroxy, nitro, CF 3 , Cl, Br, F, crosslinkable group, or substituted or unsubstituted aromatic having 5 to 40 ring atoms or a heteroaromatic ring system, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms; one or more of said R 11 -R 19 , R 110 , R 111 or R 112 may be each other / Form an aliphatic or aromatic ring system or a monocyclic or polycyclic group bonded to the ring;
  • R 31 , R 32 , R 33 or R 34 are each independently selected from: a linear alkyl group having 1 to 20 C atoms, or an alkoxy group having 1 to 20 C atoms, or having 1 to 20 C. a thioalkoxy group of an atom, or a branched or cyclic alkyl group having 3 to 20 C atoms, or an alkoxy group having 3 to 20 C atoms, or a thio group having 3 to 20 C atoms An alkoxy group, either a substituted or unsubstituted silyl group, or a substituted ketone group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or having 7 to 20 C Aromatic oxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate or isothiocyanate, hydroxy, nitro, CF 3 , Cl,
  • R 31 , R 32 , R 33 or R 34 groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and/or with a ring to which the group is bonded;
  • L represents a single bond or a linking group selected from a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy group having 5 to 40 ring atoms. Or a heteroaryloxy group;
  • One or more groups of the L may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and/or with a ring to which the group is bonded;
  • n 0, 1, 2 or 3;
  • n 0, 1, 2, 3, or 4;
  • the dashed line indicates a single bond attached to other groups.
  • a high polymer comprising repeating units consisting of the above fused ring compounds.
  • a mixture comprising the above fused ring compound or the above-mentioned high polymer and organic functional material, the organic functional material being selectable from: hole injection or transport material, hole blocking material, electron injecting or transporting material, electron blocking Materials, organic matrix materials, singlet emitters, triplet emitters, thermally excited delayed fluorescent materials, and organic dyes.
  • a composition comprising the above fused ring compound or the above high polymer or a mixture thereof, and an organic solvent.
  • An organic electronic device comprising the above fused ring compound or the above polymer or a mixture thereof.
  • the above fused ring compound has a fluorescence emission having an emission wavelength at a short wavelength, and its luminescence spectrum exhibits a narrow half-peak width, so that the substance has a deep blue fluorescence emission and has high luminous efficiency.
  • the organic electroluminescent device prepared by using such an aromatic amine derivative as a guest has dark blue color coordinates, high luminous efficiency, and long device lifetime.
  • FIG. 1 is a structural view of a light emitting device according to an embodiment.
  • the host material In the present invention, the host material, the matrix material, the Host material, and the Matrix material have the same meaning and are interchangeable.
  • metal organic complexes metal organic complexes, metal organic complexes, and organometallic complexes have the same meaning and are interchangeable.
  • composition printing ink, ink, and ink have the same meaning and are interchangeable.
  • D n means that there are n D, for example, “D 4 " means that there are four deuterium atoms substituted, and D 1 to D 4 means that it contains 1-4 deuterium atoms.
  • substitution of a hydrogen atom by a deuterium atom means that one or more hydrogen atoms in Ar 6 may or may not be substituted by a deuterium atom.
  • the present invention provides a fused ring compound of the formula (I):
  • X 1 is CR 1 R 2 , O, S, NR 3 .
  • X 1 is CR 1 R 2 or NR 3 .
  • X 1 is O or S.
  • R 1 , R 2 or R 3 are each independently selected from: H, or a linear alkyl group having 1 to 20 C atoms, or an alkoxy group having 1 to 20 C atoms, or 1 to 20 C. a thioalkoxy group of an atom, or a branched or cyclic alkyl group having 3 to 20 C atoms, or an alkoxy group having 3 to 20 C atoms, or a thio group having 3 to 20 C atoms
  • At least one of R 11 -R 19 , R 110 , R 111 or R 112 contains a structure as shown in the general formula (III), and the other substituents are each independently selected from: H or a straight having 1 to 20 C atoms.
  • Keto group or alkoxycarbonyl group having 2 to 20 C atoms, or aryloxycarbonyl group having 7 to 20 C atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate , thiocyanate or isothiocyanate, hydroxy, nitro, CF 3 , Cl, Br, F, crosslinkable group, or substituted or unsubstituted aromatic having 5 to 40 ring atoms or a heteroaromatic ring system, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms; one or more of said R 11 -R 19 , R 110 , R 111 or R 112 may be each other / Or form a monocyclic or polycyclic aliphatic or aromatic ring system with the group bonded to the ring; the R 11 -R 19, R 110, one of R 112 R 111 or more or optionally Further replaced by D;
  • R 11 -R 19 , R 110 , R 111 or R 112 contains a structure as shown in the general formula (III), and the other substituents are each independently selected from: H or have 1 to a linear alkyl group of 10 C atoms, or an alkoxy group having 1 to 10 C atoms, or a thioalkoxy group having 1 to 10 C atoms, or a branch having 3 to 10 C atoms or a cyclic alkyl group, or an alkoxy group having 3 to 10 C atoms, or a thioalkoxy group having 3 to 10 C atoms, or a substituted or unsubstituted silyl group, or having 1 to 10 a substituted keto group of a C atom, or an alkoxycarbonyl group having 2 to 10 C atoms, or an aryloxycarbonyl group having 7 to 10 C atoms, a cyano group (-CN), a carbamoyl group (-C)
  • R 31 , R 32 , R 33 or R 34 are each independently selected from: a linear alkyl group having 1 to 20 C atoms, or an alkoxy group having 1 to 20 C atoms, or having 1 to 20 C. a thioalkoxy group of an atom, or a branched or cyclic alkyl group having 3 to 20 C atoms, or an alkoxy group having 3 to 20 C atoms, or a thio group having 3 to 20 C atoms
  • L represents a single bond or a linking group.
  • the linking group may be a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms;
  • One or more groups may form a polycyclic aliphatic or aromatic ring system with each other and/or a ring bonded to the group; one or more of the various groups described above are optionally selected Further replaced by D.
  • L is a deuterated or undeuterated substituted or unsubstituted aromatic or heteroaromatic ring system having from 5 to 30 ring atoms, or from 5 to 30 deuterated or unsubstituted.
  • An aryloxy or heteroaryloxy group of one ring atom; one or more groups of said L may form a polycyclic aliphatic or aromatic ring system with each other and/or a ring bonded to said group .
  • L is deuterated or undeuterated substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 20 ring atoms, or deuterated or unsubstituted having 5 to An aryloxy or heteroaryloxy group of 20 ring atoms; one or more of the groups of L may form a polycyclic aliphatic or aromatic ring with each other and/or with a ring to which the group is bonded system.
  • n is 0, 1, 2, or 3; in one embodiment, m is 0, 1, or 2; in one embodiment, m is 0 or 1.
  • n is 0, 1, 2, 3, or 4; in one embodiment, n is 0, 1, 2, or 3; in one embodiment, n is 0, 1, or 2; In one embodiment, n is 0 or 1.
  • the dashed line indicates a single bond attached to other groups.
  • At least one of R 1 -R 3 , R 11 -R 19 , R 110 , R 111 or R 112 comprises an aromatic or heteroaromatic ring system.
  • the aromatic ring system comprises from 5 to 15 carbon atoms in the ring system; in one embodiment, the aromatic ring system comprises from 5 to 10 carbon atoms in the ring system; in one embodiment, the heteroaromatic The ring system contains from 2 to 15 carbon atoms in the ring system, and at least one hetero atom having a total number of carbon atoms and heteroatoms of at least four.
  • the heteroaromatic ring system contains from 2 to 10 carbon atoms in the ring system, and at least one heteroatom, the total number of carbon atoms and heteroatoms being at least 4.
  • the hetero atom is selected from the group consisting of Si, N, P, O, S, and/or Ge; in one embodiment, the hetero atom is selected from the group consisting of Si, N, P, O, and/or S; in one embodiment, the hetero atom is preferably selected. From N, O or S.
  • the above aromatic ring system or aromatic group means a hydrocarbon group containing at least one aromatic ring, and includes a monocyclic group and a polycyclic ring system.
  • the heteroaromatic ring or heteroaromatic group described above refers to a hydrocarbon group (containing a hetero atom) containing at least one heteroaromatic ring, and includes a monocyclic group and a polycyclic ring system.
  • These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, a fused ring. At least one of these rings of the polycyclic ring is aromatic or heteroaromatic.
  • aromatic or heteroaromatic ring systems include not only aromatic or heteroaromatic systems, but also multiple aryl or heteroaryl groups may also be interrupted by short non-aromatic units ( ⁇ 10%).
  • Non-H atoms preferably less than 5% of non-H atoms, such as C, N or O atoms).
  • systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc., are also considered to be aromatic ring systems for the purposes of the present invention.
  • examples of the aromatic group are: benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, anthracene, benzopyrene, triphenylene, anthracene, anthracene, snail, and derivatives thereof.
  • heteroaromatic groups are: furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole , thiazole, tetrazole, anthracene, oxazole, pyrroloimidazole, pyrrolopyrrol, thienopyrrole, thienothiophene, furopyrrol, furanfuran, thienofuran, benzisoxazole, benzisothiazole , benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-naphthyridine, quinoxaline, phenanthridine, pyridine, quinazoline, quinazolinone,
  • At least one of R 11 -R 19 , R 110 , R 111 or R 112 contains a structure as shown in the formula (III), and each of the other substituents Independently selected from the following structures:
  • n is 0, 1, 2, or 3; in one embodiment, m is 0, 1, or 2; in one embodiment, m is 0 or 1.
  • n, p or s are each independently 0, 1, 2, 3 or 4; in an embodiment, n, p or s are each independently 0, 1, 2 or 3; In an embodiment, n, p or s are each independently 0, 1 or 2; in one embodiment, n, p or s are each independently 0 or 1.
  • t or q is 0, 1, 2, 3, 4 or 5; in one embodiment, t or q is 0, 1, 2 or 3; in one embodiment, t or q is 0, 1 or 2; in an embodiment, t or q is 0 or 1.
  • A is a saturated cycloalkane having 3 to 8 C atoms. In one embodiment, A is a saturated cycloalkane having 4 to 6 C atoms. In one embodiment, A is a saturated cycloalkane having from 5 to 6 C atoms.
  • the structure of formula (III) can be selected from:
  • R 55 -R 59 or R 511- R 548 are each independently selected from: a linear alkyl group having 1 to 20 C atoms, or an alkoxy group having 1 to 20 C atoms, or having 1 to 20 C a thioalkoxy group of an atom, or a branched or cyclic alkyl group having 3 to 20 C atoms, or an alkoxy group having 3 to 20 C atoms, or a thio group having 3 to 20 C atoms
  • n 0, 1, 2 or 3; in one embodiment, m is 0, 1 or 2; in one embodiment, m is 0 or 1.
  • n is 0, 1, 2, 3 or 4; in one embodiment, n is 0, 1, 2 or 3; in one embodiment, n is 0, 1 or 2; in one embodiment, n is 0 or 1.
  • s is 1, 2, 3, 4 or 5; in one embodiment, s is 0, 1, 2 or 3; in one embodiment, s is 0, 1 or 2; in an embodiment, s is 0 or 1.
  • u is 0, 1, 2, 3, 4, 5 or 6; in one embodiment, u is 0, 1, 2, 3, 4 or 5; in one embodiment, u is 0, 1, 2 or 3; In an embodiment, u is 0, 1, or 2; in one embodiment, u is 0 or 1.
  • v is 0, 1, 2, 3, 4, 5, 6 or 7; in one embodiment, v is 0, 1, 2 or 3; in one embodiment, v is 0, 1 or 2; In the embodiment, v is 0 or 1.
  • L represents a single bond or a linking group.
  • the linking group may be a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms;
  • One or more groups may form a polycyclic aliphatic or aromatic ring system with each other and/or a ring bonded to the group; one or more of the various groups described above are optionally selected Further replaced by D.
  • the dashed line indicates a single bond attached to other groups.
  • L is deuterated or undeuterated substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 30 ring atoms, or deuterated or unsubstituted having 5 to An aryloxy or heteroaryloxy group of 30 ring atoms, or a combination of these systems, wherein one or more of the groups may form a polycyclic aliphatic group or/and a ring to which the group is bonded Aromatic ring system.
  • L is deuterated or undeuterated substituted or unsubstituted aromatic or heteroaromatic ring system having 10 to 25 ring atoms, or deuterated or unsubstituted having 10 to a 25 ring atom aryloxy or heteroaryloxy group, or a combination of these systems, wherein one or more groups may form a polycyclic aliphatic or a ring bonded to each other and/or to the group Aromatic ring system.
  • the L linking group described in the above general formulas is preferably selected from a single bond.
  • linking group L described above comprises the structural formula:
  • X 1 is CR 61 or N
  • R 61 - R 66 are each independently selected from: H, or a linear alkyl group having 1 to 20 C atoms, or an alkoxy group having 1 to 20 C atoms, or sulfur having 1 to 20 C atoms.
  • the L linking group described in the above general formulas is selected from the following structures:
  • the dotted line indicates a single bond linked to other groups.
  • the compound has the structure shown in the general formula (IV):
  • X 1 is CR 1 R 2 , O, S, NR 3 .
  • X 1 is CR 1 R 2 .
  • X 1 is O or S.
  • R 1 , R 2 or R 3 are each independently selected from: H, or a linear alkyl group having 1 to 20 C atoms, or an alkoxy group having 1 to 20 C atoms, or 1 to 20 C. a thioalkoxy group of an atom, or a branched or cyclic alkyl group having 3 to 20 C atoms, or an alkoxy group having 3 to 20 C atoms, or a thio group having 3 to 20 C atoms
  • R 1 , R 2 or R 3 are each independently selected from a linear alkyl group having 1 to 10 C atoms or an alkane having 1 to 10 C atoms.
  • R 13 , R 15 or R 111 are as defined in the formula (I).
  • R 13 , R 15 or R 111 are each independently selected from: H, or a linear alkyl group having 1 to 10 C atoms, or 1 to 10 C.
  • At least one of R 13 , R 15 or R 111 comprises:
  • R 21 or R 22 are each independently selected from a hydrogen atom or a group:
  • R 21 or R 22 are each independently selected from the group consisting of:
  • a specific example of a fused ring compound according to the present invention is as follows, but is not limited thereto:
  • the fused ring compounds according to the present invention have an emission wavelength between 300 and 800 nm, preferably between 350 and 600 nm, more preferably between 400 and 500 nm.
  • the fused ring compound according to the present invention has a higher photoluminescence quantum efficiency, generally ⁇ 15%, preferably ⁇ 25%, more preferably ⁇ 35%, and most preferably ⁇ 50%.
  • the fused ring compound according to the present invention has a glass transition temperature of ⁇ 100 ° C, preferably ⁇ 110 ° C, more preferably ⁇ 120 ° C, and most preferably ⁇ 140 ° C.
  • the compound according to the invention is at least partially deuterated, preferably 10% of H is deuterated, more preferably 20% of H is deuterated, and very preferably 30% of H is deuterated It is best to have 40% of H being deuterated.
  • the invention further relates to a high polymer having at least one repeating unit comprising the above fused ring compound.
  • the high polymer is a non-conjugated high polymer wherein the structural unit of formula (I) or (IV) is on the side chain.
  • the high polymer is a conjugated high polymer.
  • the present invention also relates to a method for synthesizing an organic compound according to the general formulae (I) to (IV), wherein a reaction is carried out using a raw material containing a reactive group.
  • active materials comprise at least one leaving group, for example, bromine, iodine, boric acid or a boronic ester.
  • Suitable reactions to form C-C linkages are well known to those skilled in the art and are described in the literature.
  • Particularly suitable and preferred coupling reactions are SUZUKI, STILLE and HECK coupling reactions.
  • the present invention also provides a mixture comprising the above fused ring compound or high polymer and an organic functional material, the organic functional material being selected from: hole (also called hole) injection or transport material (HIM/HTM) , hole blocking material (HBM), electron injecting or transporting material (EIM/ETM), electron blocking material (EBM), organic matrix material (Host), singlet illuminant (fluorescent illuminant), triplet illuminant ( Phosphorescent emitters, thermally excited delayed fluorescent materials (TADF materials) and organic dyes.
  • hole also called hole injection or transport material
  • HBM hole blocking material
  • EIM/ETM electron injecting or transporting material
  • EBM electron blocking material
  • organic matrix material Host
  • singlet illuminant fluorescent illuminant
  • triplet illuminant Phosphorescent emitters
  • TADF materials thermally excited delayed fluorescent materials
  • the mixture comprises the above fused ring compound or polymer, and a fluorescent host material (or singlet matrix material).
  • the above fused ring compound or polymer may be used as a guest, and its weight percentage is ⁇ 15% by weight, preferably ⁇ 12% by weight, more preferably ⁇ 9% by weight, still more preferably ⁇ 8% by weight, most preferably ⁇ 7% by weight.
  • the mixture comprises an organic compound or polymer according to the invention, another fluorescent illuminant (or singlet illuminant) and a fluorescent host material.
  • the organic compound according to the invention may be used as an auxiliary luminescent material in a weight ratio to another fluorescent illuminant of from 1:2 to 2:1.
  • the mixture comprises an organic compound or polymer in accordance with the present invention, and a TADF material.
  • the mixture comprises the above fused ring compound or polymer, and an HTM material.
  • HTM singlet matrix materials
  • singlet emitters singlet emitters
  • Suitable organic HIM/HTM materials may optionally comprise compounds having the following structural units: phthalocyanine, porphyrin, amine, aromatic amine, biphenyl triarylamine, thiophene, thiophene such as dithienothiophene and thiophene, pyrrole, aniline , carbazole, azide and azepine and their derivatives.
  • suitable HIMs also include self-assembling monomers such as compounds containing phosphonic acid and sliane derivatives; metal complexes and crosslinking compounds and the like.
  • An electron blocking layer is used to block electrons from adjacent functional layers, particularly the luminescent layer. Contrast one without barrier The presence of an EBL in a light-emitting device usually results in an increase in luminous efficiency.
  • the electron blocking material (EBM) of the electron blocking layer (EBL) requires a higher LUMO than an adjacent functional layer such as a light emitting layer.
  • the HBM has a larger excited state level than the adjacent luminescent layer, such as a singlet or triplet, depending on the illuminant, while the EBM has a hole transport function.
  • HIM/HTM materials that typically have high LUMO levels can be used as EBMs.
  • cyclic aromatic amine-derived compounds useful as HIM, HTM or EBM include, but are not limited to, the following general structures:
  • Each of Ar 1 to Ar 9 may be independently selected from the group consisting of a cyclic aromatic hydrocarbon compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenalrene, phenanthrene, anthracene, anthracene, fluorene, anthracene, anthracene; Heterocyclic compounds such as dibenzothiophene, dibenzofuran, furan, thiophene, benzofuran, benzothiophene, oxazole, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, evil Triazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, acesulfazine, oxadiazine, hydrazine
  • Ar 1 to Ar 9 may be independently selected from the group consisting of:
  • n is an integer from 1 to 20; X 1 to X 8 are CH or N; and Ar 1 is as defined above.
  • metal complexes that can be used as HTM or HIM include, but are not limited to, the following general structures:
  • M is a metal having an atomic weight greater than 40
  • (Y 1 -Y 2 ) is a two-dentate ligand, Y 1 and Y 2 are independently selected from C, N, O, P and S; L is an ancillary ligand; m is an integer from 1 to The maximum coordination number of this metal; m+n is the maximum coordination number of this metal.
  • (Y 1 -Y 2 ) is a 2-phenylpyridine derivative.
  • (Y 1 -Y 2 ) is a carbene ligand.
  • M is selected from Ir, Pt, Os, and Zn.
  • the HOMO of the metal complex is greater than -5.5 eV (relative to the vacuum level).
  • the example of the singlet host material is not particularly limited, and any organic compound may be used as the host as long as its singlet energy is higher than that of the illuminant, particularly the singlet illuminant or the luminescent illuminant.
  • Examples of the organic compound used as the singlet host material may be selected from the group consisting of a cyclic aromatic compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, anthracene, phenanthrene, anthracene, anthracene, fluorene, fluorene, fluorene, An aromatic heterocyclic compound such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, oxazole, carbazole, pyridine Anthraquinone, pyrrole dipyridine, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, triazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrim
  • the singlet host material can be selected from compounds comprising at least one of the following groups:
  • R 1 may be independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl;
  • Ar 1 is an aryl group Or a heteroaryl group, which has the same meaning as Ar 1 defined in the above HTM;
  • n is an integer from 0 to 20;
  • X 1 -X 8 is selected from CH or N;
  • X 9 and X 10 are selected from CR 1 R 2 Or NR 1 .
  • Singlet emitters tend to have longer conjugated pi-electron systems.
  • styrylamine and its derivatives disclosed in JP 2913116 B and WO 2001021729 A1
  • indenoindenes and derivatives thereof disclosed in WO 2008/006449 and WO 2007/140847.
  • the singlet emitter can be selected from the group consisting of monostyrylamine, dibasic styrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether and aromatic amine.
  • a monostyrylamine refers to a compound comprising an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine.
  • a binary styrylamine refers to a compound comprising two unsubstituted or substituted styryl groups and to One less amine, preferably an aromatic amine.
  • a ternary styrylamine refers to a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • a quaternary styrylamine refers to a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine.
  • a preferred styrene is stilbene, which may be further substituted.
  • the corresponding phosphines and ethers are defined similarly to amines.
  • An arylamine or an aromatic amine refers to a compound comprising three unsubstituted or substituted aromatic ring or heterocyclic systems directly bonded to a nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably selected from the fused ring system and preferably has at least 14 aromatic ring atoms.
  • Preferred examples thereof are aromatic decylamine, aromatic quinone diamine, aromatic decylamine, aromatic quinone diamine, aromatic thiamine and aromatic quinone diamine.
  • An aromatic amide refers to a compound in which a diaryl arylamine group is attached directly to the oxime, preferably at the position of 9.
  • An aromatic quinone diamine refers to a compound in which two diaryl arylamine groups are attached directly to the oxime, preferably at the 9,10 position.
  • the definitions of aromatic decylamine, aromatic quinone diamine, aromatic thiamine and aromatic quinone diamine are similar, wherein the diaryl aryl group is preferably bonded to the 1 or 1,6 position of hydrazine.
  • Further preferred singlet emitters can be selected from indenoindole-amines and indenofluorene-diamines, as disclosed in WO 2006/122630, benzoindoloindole-amines and benzoindenoindole-diamines , as disclosed in WO 2008/006449, dibenzoindolo-amine and dibenzoindeno-diamine, as disclosed in WO 2007/140847.
  • polycyclic aromatic hydrocarbon compounds in particular derivatives of the following compounds: for example, 9,10-bis(2-naphthoquinone), naphthalene, tetraphenyl, xanthene, phenanthrene , ⁇ (such as 2,5,8,11-tetra-t-butyl fluorene), anthracene, phenylene such as (4,4'-bis(9-ethyl-3-carbazolevinyl)-1 , 1 '-biphenyl), indenyl hydrazine, decacycloolefin, hexacene benzene, anthracene, spirobifluorene, aryl hydrazine (such as US20060222886), arylene vinyl (such as US5121029, US5130603), cyclopentane Alkene such as tetraphenylcyclopentadiene, rub
  • the thermally activated delayed fluorescent luminescent material is a third generation organic luminescent material developed after organic fluorescent materials and organic phosphorescent materials.
  • Such materials generally have a small singlet-triplet energy level difference ( ⁇ Est), and triplet excitons can be converted into singlet exciton luminescence by anti-intersystem crossing. This can make full use of the singlet excitons and triplet excitons formed under electrical excitation.
  • the quantum efficiency in the device can reach 100%.
  • the material structure is controllable, the property is stable, the price is cheap, no precious metal is needed, and the application prospect in the OLED field is broad.
  • the TADF material needs to have a small singlet-triplet energy level difference, preferably ⁇ Est ⁇ 0.3 eV, and secondly ⁇ Est ⁇ 0.2 eV, preferably ⁇ Est ⁇ 0.1 eV.
  • the TADF material has a relatively small ⁇ Est, and in another preferred embodiment, the TADF has a better fluorescence quantum efficiency.
  • TADF luminescent materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064( A1), Adach i, et. al. Adv. Mater., 21, 2009, 4802, Adachi, et. al. Appl. Phys. Lett., 98, 2011, 083302, Adachi, et. al. Appl. Phys.
  • TADF luminescent materials are listed in the table below:
  • the above quinone organic compound is used in an evaporation type OLED device.
  • the above quinone organic compound has a molecular weight of ⁇ 1000 g/mol.
  • the fused ring compound has a molecular weight of ⁇ 900 g/mol; in one embodiment, the fused ring compound has a molecular weight of ⁇ 850 g/mol; in one embodiment, the fused ring compound has a molecular weight of ⁇ 800 g/mol. In one embodiment, the fused ring compound has a molecular weight of ⁇ 700 g/mol.
  • Another object of the invention is to provide a material solution for printing OLEDs.
  • the fused ring compound has a molecular weight of ⁇ 700 g/mol; in one embodiment, the fused ring compound has a molecular weight of ⁇ 800 g/mol; in one embodiment, the fused ring compound The molecular weight is ⁇ 900 g/mol; in one embodiment, the molecular weight of the fused ring compound is ⁇ 1000 g/mol; in one embodiment, the molecular weight of the fused ring compound is ⁇ 1100 g/mol.
  • the present invention also provides a composition comprising the above fused ring compound or polymer or the above mixture, and an organic solvent.
  • composition according to the invention wherein the fused ring compound is useful as a singlet emitter material.
  • the above composition further comprises a host material.
  • composition comprising a host material and a singlet emitter.
  • the above composition further comprises at least two host materials.
  • the above composition further comprises a host material and a thermally activated delayed fluorescent luminescent material.
  • the above composition further comprises a hole transporting material (HTM), and more preferably, the HTM comprises a crosslinkable group.
  • HTM hole transporting material
  • the composition according to the invention is a solution.
  • composition according to the invention is a suspension.
  • the above composition may include 0.01 to 20% by weight of a fused ring compound; in one embodiment, 0.1 to 15% by weight of a fused ring compound is included in the above composition; in one embodiment, 0.2 to 10% by weight is included in the above composition
  • the fused ring compound; in one embodiment, the composition comprises from 0.25 to 5 wt% of a fused ring compound.
  • a composition wherein the solvent is selected from the group consisting of aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound Or an inorganic ester compound such as a boric acid ester or a phosphate ester, or a mixture of two or more solvents.
  • a composition according to the invention comprises at least 50% by weight of an aromatic or heteroaromatic solvent; preferably at least 80% by weight of an aromatic or heteroaromatic solvent; particularly preferably at least 90% by weight Aromatic or heteroaromatic solvents.
  • aromatic or heteroaromatic solvents are, but are not limited to, 1-tetralone, 3-phenoxytoluene, acetophenone, 1-methoxynaphthalene, p-diisopropylbenzene, pentylbenzene , tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, pair Methyl cumene, dipentylbenzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2 , 4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 1,
  • suitable and preferred solvents are aliphatic, cycloaliphatic or aromatic hydrocarbons, amines, thiols, amides, nitriles, esters, ethers, polyethers, alcohols, glycols or polyols.
  • the alcohol represents a suitable class of solvent.
  • Preferred alcohols include alkylcyclohexanols, especially methylated aliphatic alcohols, naphthols and the like.
  • the solvent may be a cycloalkane such as decalin.
  • the solvent may be used singly or as a mixture of two or more organic solvents.
  • the composition according to the present invention comprises an organic functional compound as described above and at least one organic solvent, and may further comprise another organic solvent, and examples of another organic solvent include (but not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, methylene Toluene, p-xylene, 1,4 dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, decalin, hydra
  • the solvent particularly suitable for the present invention is a solvent having Hansen solubility parameters in the following ranges:
  • ⁇ d (dispersion force) is in the range of 17.0 to 23.2 MPa 1/2 , especially in the range of 18.5 to 21.0 MPa 1/2 ;
  • ⁇ p polar forces in the range of 0.2 ⁇ 12.5MPa 1/2, especially in the 2.0 ⁇ 6.0MPa 1/2;
  • the organic solvent is selected in consideration of its boiling point parameter.
  • the organic solvent has a boiling point of ⁇ 150 ° C; preferably ⁇ 180 ° C; more preferably ⁇ 200 ° C; more preferably ⁇ 250 ° C; optimally ⁇ 275 ° C or ⁇ 300 ° C.
  • the boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead.
  • the organic solvent can be evaporated from the solvent system to form a film comprising the functional material.
  • the viscosity and surface tension parameters of a composition are:
  • the surface tension parameter should be considered when selecting the organic solvent in the above composition. Suitable ink surface tension parameters are suitable for a particular substrate and a particular printing method.
  • the organic solvent has a surface tension at 25 ° C of from about 19 dyne / cm to 50 dyne / cm; more preferably from 22 dyne / cm to 35 dyne / cm; Most preferably in the range of 25 dyne/cm to 33 dyne/cm.
  • the ink according to the present invention has a surface tension at 25 ° C of from about 19 dyne/cm to 50 dyne/cm; more preferably from 22 dyne/cm to 35 dyne/cm; preferably from 25 dyne/cm to 33dyne/cm range.
  • the viscosity parameter of the ink should be considered.
  • the viscosity can be adjusted by different methods, such as by the selection of a suitable organic solvent and the concentration of the functional material in the ink.
  • the organic solvent has a viscosity of less than 100 cps; in one embodiment, the organic solvent has a viscosity of less than 50 cps;
  • the organic solvent has a viscosity of less than 1.5 to 20 cps.
  • the viscosity herein refers to the viscosity at ambient temperature at the time of printing, and is usually 15 to 30 ° C, preferably 18 to 28 ° C, more preferably 20 to 25 ° C, and most preferably 23 to 25 ° C.
  • Compositions so formulated will be particularly suitable for ink jet printing.
  • the viscosity of the above composition ranges from about 1 cps to 100 cps at 25 °C;
  • the viscosity of the above composition ranges from 1 cps to 50 cps at 25 °C;
  • the viscosity of the above composition ranges from 1.5 cps to 20 cps at 25 °C.
  • An ink obtained by an organic solvent satisfying the above boiling point and surface tension parameters and viscosity parameters can be formed to have a uniform thickness And a functional material film of a compositional nature.
  • Another object of the invention is to provide the use of an upper compound in an organic electronic device.
  • the organic electronic device can be selected from an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, and an organic Lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diode).
  • OLED organic light emitting diode
  • OCV organic photovoltaic cell
  • OFET organic field effect transistor
  • OFET organic light emitting field effect transistor
  • organic Lasers organic spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diode).
  • Another object of the present invention is to provide a method of producing the above electronic device.
  • the above compound is formed into a functional layer on a substrate by evaporation, or a functional layer is formed on a substrate by co-evaporation with at least one other organic functional material, or
  • the above composition is applied to a substrate by printing or coating to form a functional layer, wherein the printing or coating method can be selected from, but not limited to, inkjet printing, Nozzle Printing, typography , screen printing, dip coating, spin coating, blade coating, roller printing, torsion roll printing, lithography, flexographic printing, rotary printing, spray coating, brush coating or pad printing, slit extrusion coating Wait.
  • the invention further relates to the use of the composition as a printing ink in the preparation of an organic electronic device, particular preference being given to a preparation process by printing or coating.
  • suitable printing or coating techniques include, but are not limited to, inkjet printing, typography, screen printing, dip coating, spin coating, blade coating, roller printing, twist roll printing, lithography, flexography Printing, rotary printing, spraying, brushing or pad printing, slit-type extrusion coating, etc.
  • Preferred are gravure, screen printing and inkjet printing. Gravure printing, ink jet printing will be applied in embodiments of the invention.
  • the solution or suspension may additionally comprise one or more components such as surface active compounds, lubricants, wetting agents, dispersing agents, hydrophobic agents, binders and the like for adjusting viscosity, film forming properties, adhesion, and the like.
  • the functional layer is formed to have a thickness of 5 nm to 1000 nm.
  • the present invention further relates to an organic electronic device which is an organic electroluminescent device comprising a light-emitting layer formed of the above fused ring compound or the above-described high polymer or a mixture thereof.
  • an organic electronic device comprises at least one cathode, an anode and a functional layer between the cathode and the anode, wherein the functional layer contains at least the above fused ring compound or the above-mentioned high polymer or the above mixture.
  • the organic electronic device described above is an electroluminescent device, particularly an OLED (shown in FIG. 1), comprising a substrate 101, an anode 102, an emissive layer 104, and a cathode 106.
  • OLED shown in FIG. 1
  • the substrate 101 can be opaque or transparent.
  • a transparent substrate can be used to make a transparent light-emitting component. See, for example, Bulovic et al. Nature 1996, 380, p29, and Gu et al, Appl. Phys. Lett. 1996, 68, p2606.
  • the substrate can be rigid or elastic.
  • the substrate can be plastic, metal, semiconductor wafer or glass.
  • the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice.
  • the substrate is flexible, optionally in the form of a polymer film or plastic, having a glass transition temperature Tg of 150 ° C or higher, preferably more than 200 ° C, more preferably more than 250 ° C, preferably More than 300 ° C. Examples of suitable flexible substrates are poly(ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN).
  • PET poly(ethylene terephthalate)
  • PEN polyethylene glycol (2,6-n
  • the anode 102 can comprise a conductive metal or metal oxide, or a conductive polymer.
  • the anode can easily inject holes into a hole injection layer (HIL) or a hole transport layer (HTL) or a light-emitting layer.
  • HIL hole injection layer
  • HTL hole transport layer
  • the absolute value of the difference between the work function of the anode and the HOMO level or the valence band level of the illuminant in the luminescent layer or the p-type semiconductor material as the HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV.
  • anode material examples include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like.
  • suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art.
  • the anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices in accordance with the present invention.
  • Cathode 106 can include a conductive metal or metal oxide.
  • the cathode can easily inject electrons into EIL or ETL or straight Connected to the luminescent layer.
  • the work function of the cathode and the LUMO level of the illuminant or the n-type semiconductor material as an electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) in the luminescent layer or
  • the absolute value of the difference in conduction band energy levels is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV.
  • all materials which can be used as cathodes for OLEDs are possible as cathode materials for the devices of the invention.
  • cathode material examples include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF2/Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like.
  • the cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
  • the OLED may further comprise other functional layers such as a hole injection layer (HIL) or a hole transport layer (HTL) (103), an electron blocking layer (EBL), an electron injection layer (EIL) or an electron transport layer (ETL) (105). ), a hole blocking layer (HBL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the light-emitting layer 104 is vacuum-deposited, the evaporation source of which comprises a compound according to the invention.
  • the light-emitting layer 104 is prepared by printing the composition according to the present invention.
  • the electroluminescent device according to the invention has an emission wavelength of between 300 and 1000 nm, preferably between 350 and 900 nm, more preferably between 400 and 800 nm.
  • the invention further relates to the use of an organic electronic device according to the invention in various electronic devices, including, but not limited to, display devices, illumination devices, light sources, sensors and the like.
  • the invention further relates to an electronic device comprising an organic electronic device according to the invention, including, but not limited to, a display device, a lighting device, a light source, a sensor and the like.
  • HIL a triarylamine derivative
  • HTL a triarylamine derivative
  • a, cleaning of the conductive glass substrate when used for the first time, can be washed with a variety of solvents, such as chloroform, ketone, isopropyl alcohol, and then UV ozone plasma treatment;
  • HIL 50 nm
  • HTL 35 nm
  • EML 25 nm
  • ETL 28 nm
  • cathode LiQ / Al (1nm / 150nm) in a high vacuum (1 ⁇ 10 -6 mbar) in the thermal evaporation;
  • the device is encapsulated in a nitrogen glove box with an ultraviolet curable resin.
  • the current-voltage (J-V) characteristics of each OLED device are characterized by characterization equipment while recording important parameters such as efficiency, lifetime and external quantum efficiency. It has been found that the color coordinates of the blue light device prepared by using Compound 1 - Compound 4 as the EML layer illuminant are better than that of Comparative Compound 1, for example, the color coordinates of the device prepared by Compound 3 are (0.149, 0.078); The luminous efficiency of the blue light device prepared by the compound 4 as the EML layer illuminant is in the range of 6-8 cd/A, which has more excellent luminous efficiency; in terms of device lifetime, the blue light device is prepared by using the compound 1 - compound 4 as the EML layer illuminant. The lifetime is better than that of Comparative Compound 1, for example, the device prepared by Compound 3 has a T95 of 1.7 times that of Comparative Compound 1 at 1000 nits.

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Abstract

La présente invention concerne un composé cyclique fusionné, son procédé de préparation et une application associée. Le composé cyclique fusionné est représenté par la formule générale (I). Le composé cyclique fusionné émet une fluorescence à une courte longueur d'onde, et son spectre d'émission de lumière présente une largeur totale étroite à mi-hauteur. En conséquence, un tel matériau présente une émission de fluorescence bleu sombre et une efficacité d'émission de lumière élevée. Un élément électroluminescent organique préparé par un tel dérivé d'amine aromatique en tant qu'hôte a des coordonnées de chromaticité du bleu sombre, une efficacité d'émission de lumière élevée, et permet une longue durée de vie du dispositif.
PCT/CN2017/113943 2016-11-30 2017-11-30 Composé cyclique fusionné, son procédé de préparation et son application WO2018099432A1 (fr)

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WO2010053210A1 (fr) * 2008-11-06 2010-05-14 Canon Kabushiki Kaisha Composé d'indénopyrène et dispositif électroluminescent organique utilisant le composé
WO2011037429A2 (fr) * 2009-09-28 2011-03-31 덕산하이메탈(주) Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique
CN105514288A (zh) * 2014-10-13 2016-04-20 环球展览公司 新颖化合物和在装置中的用途

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Publication number Priority date Publication date Assignee Title
WO2010053210A1 (fr) * 2008-11-06 2010-05-14 Canon Kabushiki Kaisha Composé d'indénopyrène et dispositif électroluminescent organique utilisant le composé
WO2011037429A2 (fr) * 2009-09-28 2011-03-31 덕산하이메탈(주) Composés ayant des dérivés hétérocycliques à cycle aryle condensé de 5 chaînons, dispositif électronique organique utilisant les composés, et terminal comprenant le dispositif électronique organique
CN105514288A (zh) * 2014-10-13 2016-04-20 环球展览公司 新颖化合物和在装置中的用途

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