WO2020218680A1 - Composé organique et diode électroluminescente organique l'utilisant - Google Patents

Composé organique et diode électroluminescente organique l'utilisant Download PDF

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WO2020218680A1
WO2020218680A1 PCT/KR2019/009280 KR2019009280W WO2020218680A1 WO 2020218680 A1 WO2020218680 A1 WO 2020218680A1 KR 2019009280 W KR2019009280 W KR 2019009280W WO 2020218680 A1 WO2020218680 A1 WO 2020218680A1
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aryl
compound
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이용환
박호철
엄민식
심재의
박정근
김영모
박우재
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두산솔루스 주식회사
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel organic light-emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent thermal stability, electrochemical stability, and hole transport ability, and by including the same in one or more organic material layers, luminous efficiency, driving voltage, and lifetime It relates to an organic electroluminescent device having improved properties such as.
  • organic electroluminescent device In an organic electroluminescent device (hereinafter, referred to as “organic EL device”), when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to their function.
  • the light-emitting materials of the organic EL device may be classified into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials for realizing better natural colors according to light emission colors.
  • a host/dopant system may be used as a light emitting material.
  • the dopant material can be classified into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 materials for the hole blocking layer and the electron transport layer
  • anthracene derivatives have been reported as materials for the light emitting layer.
  • metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2 , which have advantages in terms of efficiency improvement, among the light emitting layer materials are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
  • Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2
  • red is used as a phosphorescent dopant material
  • CBP 4,4-dicarbazolybiphenyl
  • An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device and is excellent in thermal stability, electrochemical stability, and hole transport capability, and thus can be used as a material for a hole transport layer.
  • another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, exhibiting a low driving voltage and high luminous efficiency, and improving lifespan.
  • X is O or S
  • a, b, c, and d are each an integer of 0 to 3
  • L 1 , L 2 , L 3 and L 4 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of an arylene group of C 6 to C 60 and a heteroarylene group having 5 to 60 nuclear atoms ,
  • Ar 1 to Ar 6 are the same as or different from each other, and are each independently selected from the group consisting of an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,
  • e and f are each an integer of 0 to 4,
  • R 1 and R 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C Selected from the group consisting of an aryl boron group of 60 , an arylphosphine group of C 6 to C 60 , and an aryl phosphine oxide group of C 6 to C 60 , or con
  • the present invention is a positive electrode; cathode; And one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises a compound represented by Formula 1 do.
  • the compound of the present invention has excellent thermal stability, electrochemical stability, and hole transport ability, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full-color display panel or the like because the light emitting performance, driving voltage, lifespan, and efficiency are greatly improved.
  • FIG. 1 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • FIG. 2 is a schematic cross-sectional view of an organic electroluminescent device according to another example of the present invention.
  • 300 organic material layer
  • 310 hole injection layer
  • the present invention provides a novel organic compound that is excellent in electrochemical stability, thermal stability, and carrier transport capability (especially, hole transport capability) and can be used as a material for a high-efficiency hole transport layer.
  • the compound represented by Formula 1 according to the present invention is either a spiro [fluorene-xanthene] moiety or a spyro [fluorene-thioxathene] moiety It includes a core structure formed by introducing a substituent of an amine group-linker group-amine group structure directly or through a linker at the benzene site of
  • the compound of Formula 1 includes a spiro[fluorene-xanthene] moiety or a spiro[fluorene-thioxanthene] moiety, and thus has high hole mobility and excellent hole transporting ability. This is between the HOMO and LUMO energy levels of the hole injection layer and the emission layer, and hole injection and transfer are smooth. Accordingly, when the compound of the present invention is used as a material for the hole transport layer and the organic electroluminescent device is included, not only the luminous efficiency of the organic electroluminescent device is improved, but the driving voltage is lowered to increase the lifespan.
  • the compound of Formula 1 has an amine group-linker group-amine group structure substituent introduced at any one of the benzene moieties in the above-described moiety, due to physicochemical properties such as amorphous properties and high refractive index properties. The luminous efficiency can be further improved.
  • the compound of Formula 1 since the compound of Formula 1 has a high glass transition temperature (Tg), it is not only excellent in stability, but also excellent in electrochemical stability.
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability, electrochemical stability, and hole transport properties. Accordingly, the compound represented by Formula 1 of the present invention may be used as an organic material layer material of an organic electroluminescent device, preferably a hole transport layer material or a hole transport auxiliary layer material, more preferably a hole transport layer material.
  • the performance and lifetime characteristics of the organic electroluminescent device including the compound of the present invention can be greatly improved, and the performance of a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also be maximized.
  • X is O or S.
  • the compound of Formula 1 has excellent amphoteric properties of electrons and holes, and thus has excellent carrier transport capability. Therefore, when the compound of Formula 1 according to the present invention is used as a material for a hole transport layer, an effect of improving efficiency and driving voltage may be improved by improving hole transport capability.
  • the compound represented by Formula 1 is a compound represented by Formula 2 or 3 below.
  • X, L 1 to L 4 , Ar 1 to Ar 6 , R 1 , R 2 , a, b, c, d, e and f are the same as defined in Formula 1, respectively.
  • These compounds of Formulas 2 and 3 are Moiety or It may be a compound represented by any one of the following Formulas 4 to 10 depending on the position of the moiety introduced (bonded).
  • X, L 1 to L 4 , Ar 1 to Ar 6 , R 1 , R 2 , a, b, c, d, e and f are the same as defined in Formula 1, respectively.
  • a, b, c, and d are each an integer of 0 to 3, preferably 0 or 1.
  • each of L 1 to L 4 is a divalent linker, the same or different from each other, and each independently C 6 to C It is selected from the group consisting of an arylene group of 60 and a heteroarylene group having 5 to 60 nuclear atoms, and specifically selected from the group consisting of an arylene group of C 6 to C 30 and a heteroarylene group having 5 to 30 nuclear atoms have.
  • b and d are each an integer of 1 to 3
  • L 2 and L 4 are the same as or different from each other, and each independently an arylene group of C 6 to C 60 and the number of nuclear atoms from 5 to It may be selected from the group consisting of 60 heteroarylene groups.
  • L 1 and L 3 are the same as or different from each other, and each independently may be a single bond, or may be selected from the group consisting of an arylene group of C 6 to C 60 and a heteroarylene group having 5 to 60 nuclear atoms.
  • L 1 , L 2 , L 3 and L 4 are the same as or different from each other, and each independently may be a single bond or may be selected from the group consisting of the linker groups Link1 to Link7 below, but is not limited thereto.
  • Y 1 is selected from the group consisting of O, S, C(R 4 )(R 5 ), and Si(R 6 )(R 7 ),
  • g, h, i, j, k, l are each an integer of 0 to 4
  • m is an integer of 0 to 6
  • n is an integer of 0 to 8
  • o is an integer of 0 to 6
  • p is 0
  • q and r are each an integer of 0 to 3
  • At least one R 3 is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alky Nyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyl jade of C 1 to C 40 Group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting of an
  • R 4 to R 7 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyl of C 1 to C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the group consisting of C 60
  • the condensed ring may be a C 6 ⁇ C 20 condensed aromatic ring, or a 5 to 20 membered condensed heteroaromatic ring, and the heterocycloalkyl group, heteroaryl group and condensed heteroaromatic ring are each N, S , O and Se may contain at least one hetero atom selected from the group consisting of.
  • Ar 1 to Ar 6 are the same as or different from each other, and each independently selected from the group consisting of an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms
  • each independently C 6 ⁇ C 30 may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms.
  • Ar 1 to Ar 6 may be the same as or different from each other, and each independently may be selected from the group consisting of substituents S1 to S13, but is not limited thereto.
  • Y 1 is selected from the group consisting of O, S, C(R 4 )(R 5 ), and Si(R 6 )(R 7 ),
  • g, i, l are each an integer of 0 to 5
  • h, j, k, p, r, s are each an integer of 0 to 4
  • m is an integer of 0 to 7
  • n is an integer of 0 to 9
  • o is an integer of 0 to 7
  • q, t, u, and v are integers of 0 to 3
  • w and x are each an integer of 0 to 2
  • At least one R 3 is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alky Nyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyl jade of C 1 to C 40 Group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting of an
  • R 4 to R 7 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 Alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyl of C 1 to C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the group consisting of C 60
  • the condensed ring may be a C 6 ⁇ C 20 condensed aromatic ring, or a 5 to 20 membered condensed heteroaromatic ring, and the heterocycloalkyl group, heteroaryl group and condensed heteroaromatic ring are each N, S , O and Se may contain at least one hetero atom selected from the group consisting of.
  • e and f are each an integer of 0 to 4.
  • R 1 and 1 or more R 2 are The same or different from each other, and each independently deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl
  • the heterocycloalkyl group and the heteroaryl group each include at least one heteroatom selected from the group consisting of N, S, O and Se.
  • e and f are each 0, and R 1 and R 2 are hydrogen.
  • e and f may be 1, and R 1 and R 2 may each be a phenyl group or a biphenyl group.
  • the boron group, arylphosphine group, arylphosphine oxide group and condensed ring are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms,
  • the heterocycloalkyl group and the heteroaryl group may each include one or more heteroatoms selected from the group consisting of N, S, O, and Se.
  • the compound represented by Formula 1 according to the present invention may be embodied as a compound represented by any one of the following Formulas 11 to 24, but is not limited thereto.
  • Each X is as defined in Formula 1;
  • R 1 and R 2 are each as defined in Formula 1, specifically the same or different from each other, and each independently may be selected from the group consisting of hydrogen, a phenyl group and a biphenyl group, and more specifically, of R 1 and R 2 One of them may be hydrogen and the rest may be a phenyl group or a biphenyl group;
  • Y 1 is selected from the group consisting of O, S, C(R 4 )(R 5 ), and Si(R 6 )(R 7 );
  • a plurality of Y 2 may be the same as or different from each other, N or CR 8 , specifically, all of the plurality of Y 2 may be CH, or one of the plurality of Y 2 may be N and the rest may be CH;
  • g is an integer of 0 to 4, specifically an integer of 0 to 2;
  • At least one R 3 and R 4 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting
  • R 3 -It can be condensed with another R 3 ) to form a condensed ring, specifically each independently hydrogen, phenyl group, naphthyl group, monovalent dibenzothiophene group, monovalent dibenzofuran group, monovalent fluorene It may be selected from the group consisting of a group, a monovalent pyridine group, a methyl group, an ethyl group, a propyl group, and a butyl group.
  • the compound represented by Formula 1 according to the present invention described above may be further specified as Compound 1 to Compound 270, but is not limited thereto.
  • alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.
  • alkynyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.
  • cycloalkyl refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
  • heterocycloalkyl refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
  • heterocycloalkyl include morpholine and piperazine, but are not limited thereto.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms such as N, O, S or Se.
  • heteroatoms such as N, O, S or Se.
  • a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • aryloxy is a monovalent substituent represented by RO-, and R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
  • alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di- and tri-alkylsilyl.
  • arylsilyl refers to silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.
  • alkyl boron group refers to a boron group substituted with an alkyl having 1 to 40 carbon atoms
  • aryl boron group refers to a boron group substituted with an aryl having 6 to 60 carbon atoms.
  • alkylphosfinyl group refers to a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosfinyl groups.
  • arylphosphinyl group refers to a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosfinyl groups.
  • arylamine refers to an amine substituted with an aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
  • organic electroluminescent device (hereinafter, referred to as “organic EL device”) including the compound represented by Formula 1 above.
  • the organic electroluminescent device includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by Formula 1.
  • the compound may be used alone, or two or more may be used in combination.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one of the organic material layers includes the compound represented by Formula 1.
  • the organic material layer including the compound of Formula 1 may be a hole transport layer.
  • the one or more organic material layers may include a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer, and the hole transport layer may be a compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in an organic electroluminescent device as a hole transport layer material.
  • the compound of Formula 1 has a high glass transition temperature, high hole mobility, high hole transport capability, and hole injection from the hole injection layer to the emission layer due to an appropriate HOMO and LUMO energy level between the hole injection layer and the emission layer. Transfer is smooth, and has amorphous crystallinity and high refractive index characteristics. Accordingly, the organic electroluminescent device including the compound of Formula 1 may improve efficiency (luminescence efficiency and power efficiency), lifespan, luminance, driving voltage, thermal stability, and the like.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, but, for example, an anode 100, one or more organic material layers 300, and a cathode 200 may be sequentially stacked on a substrate (FIGS. 1 and 2 Reference). In addition, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and
  • the cathode 200 may have a sequentially stacked structure.
  • an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200.
  • a hole blocking layer (not shown) may be positioned between the emission layer 330 and the electron transport layer 340.
  • the organic electroluminescent device of the present invention materials and methods known in the art, except that at least one of the organic material layers 300 (eg, hole transport layer 320) includes a compound represented by Formula 1 It can be prepared by forming an organic material layer and an electrode.
  • the organic material layers 300 eg, hole transport layer 320
  • a compound represented by Formula 1 It can be prepared by forming an organic material layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
  • the substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb
  • Conductive polymers such as polythiophene, poly
  • examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; And a multilayered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer, the light emitting layer, the electron transport layer and the electron injection layer are not particularly limited, and conventional materials known in the art may be used.
  • N-phenylspiro[fluorene-9,9'-xanthen]-3-amine (4.23 g, 10 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (3.59 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-1 (3.86 g, yield 59%) was obtained by column chromatography.
  • N-phenylspiro[fluorene-9,9'-xanthen]-2-amine (4.23 g, 10 mmol), 1-bromo-4-iodobenzene (2.82 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), and NaOt-Bu (1.9 g, 20 mmol) were added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-2 (3.29 g, yield 57%) was obtained by column chromatography.
  • N-([1,1'-biphenyl]-4-yl)spiro[fluorene-9,9'-xanthen]-4-amine (4.99 g, 10 mmol), 3-bromo-7-iododibenzo[b,d ]furan (3.72 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and 110 Stirred at °C for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-3 (4.09 g, yield 55%) was obtained by column chromatography.
  • the target compound N-(9,9-dimethyl-9H-fluoren-2-yl)spiro[fluorene-9,9'-xanthen]-1-amine (2.91) was used by column chromatography. g, yield 54%) was obtained.
  • N-(9,9-dimethyl-9H-fluoren-2-yl)spiro[fluorene-9,9'-xanthen]-1-amine (5.39 g, 10 mmol), 1-bromo-4-iodonaphthalene (3.32 g , 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene at 110° C. for 12 hours. Stirred. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-4 (3.94 g, yield 53%) was obtained by column chromatography.
  • the target compound N-(phenanthren-2-yl)spiro[fluorene-9,9'-xanthen]-4'-amine (2.72 g, yield 52%) was prepared by column chromatography. Got it.
  • N-(phenanthren-2-yl)spiro[fluorene-9,9'-xanthen]-4'-amine (5.23 g, 10 mmol), 1-bromo-8-iododibenzo[b,d]thiophene (3.89 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours I did. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-5 (4.00 g, yield 51%) was obtained by column chromatography.
  • the target compound N-([1,1':2',1''-terphenyl]-4-yl)spiro[fluorene-9,9'-xanthen] was used by column chromatography. -3'-amine (2.87 g, yield 50%) was obtained.
  • N-([1,1':2',1''-terphenyl]-4-yl)spiro[fluorene-9,9'-xanthen]-3'-amine (5.75 g, 10 mmol), 5-bromo -2-iodo-9,9-dimethyl-9H-fluorene (3.99 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-6 (4.14 g, yield 49%) was obtained by column chromatography.
  • the target compound N-(4-(pyridin-3-yl)phenyl)spiro[fluorene-9,9'-xanthen]-2'-amine (2.40 g,) was used by column chromatography. Yield 48%).
  • N-(4-(pyridin-3-yl)phenyl)spiro[fluorene-9,9'-xanthen]-2'-amine (5.00 g, 10 mmol), 3-bromo-4'-iodo-1,1 '-biphenyl (3.59 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene. The mixture was stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-7 (3.43 g, yield 47%) was obtained by column chromatography.
  • Step 1 4-phenyl-N- (triphenylen-2-yl)spiro [ fluorene -9,9'- xanthen ]-2'-amine synthesis
  • the target compound 4-phenyl-N-(triphenylen-2-yl)spiro[fluorene-9,9'-xanthen]-2'-amine (2.98 g, yield) was performed using column chromatography. 46%).
  • the target compound N-([1,1'-biphenyl]-3-yl)-2-phenylspiro[fluorene-9,9'-xanthen]-2'- was used by column chromatography. An amine (2.53 g, yield 44%) was obtained.
  • the target compound 4-(tert-butyl)-N-(4-(spiro[fluorene-9,9'-xanthen]-3-yl)phenyl)aniline ( 2.33 g, yield 42%) was obtained.
  • the target compound N-([1,1':3',1''-terphenyl]-5'-yl)-6-phenylspiro[fluorene-9,9] was used by column chromatography. '-xanthen]-3-amine (2.67 g, yield 41%) was obtained.
  • the target compound 2-([1,1'-biphenyl]-3-yl)-7-chlorospiro[fluorene-9,9'-xanthene] (2.23 g), was used by column chromatography. , Yield 43%).
  • the target compound 2-([1,1'-biphenyl]-3-yl)-N-(5,5-dimethyl-5H-dibenzo[b,d] was used by column chromatography.
  • silol-3-yl)spiro[fluorene-9,9'-xanthen]-7-amine (3.11 g, yield 44%) was obtained.
  • the target compound was 2'-([1,1'-biphenyl]-4-yl)-7'-chlorospiro[fluorene-9,9'-xanthene] ( 2.38 g, yield 46%) was obtained.
  • the target compound 2'-([1,1'-biphenyl]-4-yl)-N-mesitylspiro[fluorene-9,9'-xanthen]-7' was used by column chromatography. -amine (2.90 g, yield 47%) was obtained.
  • the target compound 4'-chloro-2-(9,9-dimethyl-9H-fluoren-2-yl)spiro[fluorene-9,9'-xanthene] was used by column chromatography. (2.73 g, yield 49%) was obtained.
  • the target compound N-(9,9'-spirobi[fluoren]-2-yl)-2-(9,9-dimethyl-9H-fluoren-2-yl) was used by column chromatography. )spiro[fluorene-9,9'-xanthen]-4'-amine (4.27 g, yield 50%) was obtained.
  • N-(9,9'-spirobi[fluoren]-2-yl)-2-(9,9-dimethyl-9H-fluoren-2-yl)spiro[fluorene-9,9'-xanthen]-4'- amine (8.54 g, 10 mmol), 1-bromo-3-iodobenzene (2.82 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-14 (4.94 g, yield 49%) was obtained by column chromatography.
  • the target compound N-(9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)spiro[fluorene-9,9'-xanthen]-3 was used by column chromatography. -amine (2.95 g, yield 48%) was obtained.
  • N-(9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)spiro[fluorene-9,9'-xanthen]-3-amine (6.15 g, 10 mmol), 1-bromo-5- Add iodonaphthalene (3.32 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) to 100 ml of Toluene and 110°C The mixture was stirred for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-15 (3.85 g, yield 47%) was obtained by column chromatography.
  • the target compound N-([1,1'-biphenyl]-4-yl)spiro[fluorene-9,9'-xanthen]-3-amine (2.29 g) was used by column chromatography. , Yield 46%) was obtained.
  • N-([1,1'-biphenyl]-4-yl)spiro[fluorene-9,9'-xanthen]-3-amine (4.99 g, 10 mmol), 4-bromo-4'-iodo-1, 1'-biphenyl (3.59 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) in 100 ml of Toluene And stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-16 (3.28 g, yield 45%) was obtained by column chromatography.
  • N-phenylspiro[fluorene-9,9'-xanthen]-2-amine (4.23 g, 10 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (3.59 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-17 (2.81 g, yield 43%) was obtained by column chromatography.
  • N-phenylspiro[fluorene-9,9'-xanthen]-4-amine (4.23 g, 10 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (3.59 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-18 (2.68 g, yield 41%) was obtained by column chromatography.
  • N-phenylspiro[fluorene-9,9'-xanthen]-4'-amine (4.23 g, 10 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (3.59 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-19 (2.68 g, yield 41%) was obtained by column chromatography.
  • N-phenylspiro[fluorene-9,9'-thioxanthen]-3'-amine (4.39 g, 10 mmol), 2-bromo-2'-iodo-1,1'-biphenyl (3.59 g, 10 mmol), Pd 2 (dba) 3 (0.91 g, 1 mmol), dppf (1.10 g, 2 mmol), NaOt-Bu (1.9 g, 20 mmol) was added to 100 ml of Toluene and stirred at 110° C. for 12 hours. After completion of the reaction, the organic layer was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the filtered organic layer, the target compound C-20 (2.88 g, yield 43%) was obtained by column chromatography.
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power Sonic 405, Hwashin Tech
  • m-MTDATA 60nm
  • Compound 1 80nm
  • DS-H522 + 5% DS-501 300nm
  • BCP 10nm
  • Alq 3 30nm
  • LiF (1nm) LiF
  • Al 200nm
  • the DS-H522 and DS-501 used at this time are products of Doosan Electronics Co., Ltd. BG
  • the structures of m-MTDATA and BCP are as follows.
  • Example 1 when forming the hole transport layer, a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were respectively used instead of the compound 1 used as the hole transport layer material.
  • Example 1 when forming the hole transport layer, a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that NPB was used instead of Compound 1 as a material for the hole transport layer.
  • the structure of the NPB used at this time is as follows.
  • Example 1 when forming the hole transport layer, a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound S-1 was used instead of Compound 1 as a material for the hole transport layer.
  • the structure of S-1 used at this time is as follows.
  • Example 1 One 4.1 25.1 Example 2 2 4.0 23.9 Example 3 3 4.2 25.2 Example 4 4 4.1 22.9 Example 5 5 3.9 24.5 Example 6 6 4.1 24.8 Example 7 7 4.2 23.5 Example 8 8 4.1 23.7 Example 9 9 4.5 22.9 Example 10 10 4.4 24.0 Example 11 11 3.8 22.8 Example 12 12 4.5 22.4 Example 13 13 3.7 25.1 Example 14 14 4.4 24.7 Example 15 15 4.1 24.1 Example 16 16 4.2 24.8 Example 17 17 4.1 20.3 Example 18 18 3.8 19.4 Example 19 19 19 3.9 21.5 Example 20 20 4.4 24.9 Comparative Example 1 NPB 5.2 18.2 Comparative Example 2 S-1 5.0 19.0
  • the organic electroluminescent devices of Examples 1 to 20 in which the compound according to the present invention is applied as a hole transport layer material are Comparative Example 1 in which NPB is applied as a hole transport layer material, and a material in which an amine group is not continuously substituted. It was confirmed that the driving voltage and current efficiency were superior to the applied organic electroluminescent device of Comparative Example 2.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé électroluminescent organique et une diode électroluminescente organique l'utilisant et, plus particulièrement, un composé ayant une stabilité thermique, une stabilité électrochimique, une capacité électroluminescente, et une capacité de transport de trous/d'électrons excellentes, et une diode électroluminescente organique comprenant le composé dans une ou plusieurs couches de celui-ci, de façon à obtenir des propriétés améliorées en termes d'efficacité lumineuse, de tension de commande, de durée de vie et analogues.
PCT/KR2019/009280 2019-04-25 2019-07-25 Composé organique et diode électroluminescente organique l'utilisant WO2020218680A1 (fr)

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US20210013420A1 (en) * 2019-07-10 2021-01-14 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
CN114478499A (zh) * 2022-01-29 2022-05-13 阜阳欣奕华材料科技有限公司 一种螺芴杂蒽类化合物及其应用
US20230040837A1 (en) * 2019-11-19 2023-02-09 Duk San Neolux Co., Ltd. Compound for organic electrical element, organic electrical element using same and electronic device thereof

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KR20150106501A (ko) * 2014-03-11 2015-09-22 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
WO2017061832A1 (fr) * 2015-10-07 2017-04-13 주식회사 엘지화학 Nouveau composé et diode électroluminescente organique comprenant celui-ci
CN106977491A (zh) * 2017-01-25 2017-07-25 孙立成 螺[芴‑9,9‑氧杂蒽]类空穴传输材料及其应用
WO2018069167A1 (fr) * 2016-10-10 2018-04-19 Merck Patent Gmbh Dispositif électronique
CN109575038A (zh) * 2017-09-28 2019-04-05 江苏三月光电科技有限公司 一种含螺氧杂蒽芴的化合物及其在有机电致发光器件上的应用
WO2019126548A1 (fr) * 2017-12-22 2019-06-27 Energy Everywhere, Inc. Matériaux de transport de trous ioniques fusionnés et réticulables pour cellules solaires en pérovskite

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KR20150106501A (ko) * 2014-03-11 2015-09-22 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
WO2017061832A1 (fr) * 2015-10-07 2017-04-13 주식회사 엘지화학 Nouveau composé et diode électroluminescente organique comprenant celui-ci
WO2018069167A1 (fr) * 2016-10-10 2018-04-19 Merck Patent Gmbh Dispositif électronique
CN106977491A (zh) * 2017-01-25 2017-07-25 孙立成 螺[芴‑9,9‑氧杂蒽]类空穴传输材料及其应用
CN109575038A (zh) * 2017-09-28 2019-04-05 江苏三月光电科技有限公司 一种含螺氧杂蒽芴的化合物及其在有机电致发光器件上的应用
WO2019126548A1 (fr) * 2017-12-22 2019-06-27 Energy Everywhere, Inc. Matériaux de transport de trous ioniques fusionnés et réticulables pour cellules solaires en pérovskite

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Publication number Priority date Publication date Assignee Title
US20210013420A1 (en) * 2019-07-10 2021-01-14 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
US20230040837A1 (en) * 2019-11-19 2023-02-09 Duk San Neolux Co., Ltd. Compound for organic electrical element, organic electrical element using same and electronic device thereof
CN114478499A (zh) * 2022-01-29 2022-05-13 阜阳欣奕华材料科技有限公司 一种螺芴杂蒽类化合物及其应用

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