[go: up one dir, main page]

WO2016122178A9 - Composé organique électroluminescent, et élément organique électroluminescent l'utilisant - Google Patents

Composé organique électroluminescent, et élément organique électroluminescent l'utilisant Download PDF

Info

Publication number
WO2016122178A9
WO2016122178A9 PCT/KR2016/000780 KR2016000780W WO2016122178A9 WO 2016122178 A9 WO2016122178 A9 WO 2016122178A9 KR 2016000780 W KR2016000780 W KR 2016000780W WO 2016122178 A9 WO2016122178 A9 WO 2016122178A9
Authority
WO
WIPO (PCT)
Prior art keywords
group
aryl
formula
alkyl
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2016/000780
Other languages
English (en)
Korean (ko)
Other versions
WO2016122178A2 (fr
WO2016122178A3 (fr
Inventor
조현종
김영배
김회문
백영미
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Doosan Corp
Original Assignee
Doosan Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Doosan Corp filed Critical Doosan Corp
Publication of WO2016122178A2 publication Critical patent/WO2016122178A2/fr
Publication of WO2016122178A3 publication Critical patent/WO2016122178A3/fr
Publication of WO2016122178A9 publication Critical patent/WO2016122178A9/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]

Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel organic compound having excellent hole injection and transporting ability, electron injection and transporting ability, light emitting ability, and the like, to one or more organic material layers.
  • the present invention relates to an organic EL device having improved characteristics such as high luminous efficiency, low driving voltage and lifetime.
  • 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 its function.
  • the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided 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. The development of such phosphorescent materials can theoretically improve the luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • Alq 3 hole blocking layer
  • anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material.
  • phosphorescent materials having a great advantage in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 as blue, green, and red dopant materials. It is used.
  • 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
  • the present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent hole injection and transporting ability, electron injection and transporting ability, and light emitting ability.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.
  • the present invention to achieve the above object provides a compound represented by the following formula (1).
  • the dotted line is the part where condensation takes place
  • X 1 and X 2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ), and Si (Ar 4 ) (Ar 5 ) At least one of X 1 and X 2 is N (Ar 1 );
  • Y 1 to Y 12 which are not condensed with the ring represented by Formula 2 to form a condensed ring, are the same or different from each other, and each independently N or C (R 1 );
  • Y 13 to Y 16 When there are a plurality of Y 13 to Y 16 , they are the same as or different from each other, and the Y 13 to Y 16 are each independently N or C (R 1 );
  • each R 1 is independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , 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 boron group, C 6 ⁇ C 60 Aryl phosphine group Or a C 6 -C 60 mono or diarylphosphinyl group and C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
  • Ar 1 to Ar 5 is independently hydrogen, C alkyl group of 1 ⁇ C 40, a cycloalkyl group of C 3 ⁇ C 40, nuclear atomic 3 To 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C 1 to C 40 alkyl silyl group, C 6 ⁇ C 60 aryl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ selected from mono or diaryl phosphine blood group and a C 6 ⁇ C 60 aryl group consisting of the C 60 amine, or by combining adjacent groups may form a condensed ring;
  • the phosphine group, mono or diarylphosphinyl group and arylamine group are each independently deuterium, halogen, cyano, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, or 3 to 40 heterocycloheteroatoms Alkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 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
  • the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
  • an organic electroluminescent device comprising a compound represented by the formula (1).
  • the organic material layer comprising the compound represented by Formula 1 is selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a light emission auxiliary layer and a life improvement layer
  • the light emitting layer including the compound represented by Chemical Formula 1 may be used as a phosphorescent host.
  • Alkyl as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 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 chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl refers to a monovalent substituent derived from a straight or branched chain 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, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from a C6 to C60 aromatic hydrocarbon combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl is meant herein monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, wherein 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, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
  • an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured.
  • Full color display panels with improved performance and lifetime can also be manufactured.
  • the present invention provides a compound represented by the following formula (1).
  • the dotted line is the part where condensation takes place
  • X 1 and X 2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ), and Si (Ar 4 ) (Ar 5 ) At least one of X 1 and X 2 is N (Ar 1 );
  • Y 1 to Y 12 which are not condensed with the ring represented by Formula 2 to form a condensed ring, are the same or different from each other, and each independently N or C (R 1 );
  • Y 13 to Y 16 When there are a plurality of Y 13 to Y 16 , they are the same as or different from each other, and the Y 13 to Y 16 are each independently N or C (R 1 );
  • each R 1 is independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , 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 boron group, C 6 ⁇ C 60 Aryl phosphine group Or a C 6 -C 60 mono or diarylphosphinyl group and C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
  • Ar 1 to Ar 5 is independently hydrogen, C alkyl group of 1 ⁇ C 40, a cycloalkyl group of C 3 ⁇ C 40, nuclear atomic 3 To 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C 1 to C 40 alkyl silyl group, C 6 ⁇ C 60 aryl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ selected from mono or diaryl phosphine blood group and a C 6 ⁇ C 60 aryl group consisting of the C 60 amine, or by combining adjacent groups may form a condensed ring;
  • the phosphine group, mono or diarylphosphinyl group and arylamine group are each independently deuterium, halogen, cyano, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, or 3 to 40 heterocycloheteroatoms Alkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 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
  • novel organic compounds according to the present invention are dibenzoazine (5H-dibenzo [b, f] azepine), dibenzooxepine (dibenzo [b, f] oxepine), dibenzothiepine (dibenzo [b, f] thiepine), 5H-dibenzo [b, f] silepine, or a 5-membered heteroaromatic ring moiety condensed with naphthyl to 5H-dibenzo [a, d] cycloheptene.
  • dibenzoazine (5H-dibenzo [b, f] azepine)
  • dibenzooxepine dibenzo [b, f] oxepine
  • dibenzothiepine dibenzo [b, f] thiepine
  • 5H-dibenzo [b, f] silepine or a 5-membered heteroaromatic
  • novel organic compound according to the present invention is characterized by represented by the following formula (1).
  • the dotted line is the part where condensation takes place
  • X 1 and X 2 are the same as or different from each other, and are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ), and Si (Ar 4 ) (Ar 5 ) At least one of X 1 and X 2 is N (Ar 1 ), preferably X 1 is selected from the group consisting of O, S and N (Ar 1 ), and X 2 is N (Ar 1 ) ;
  • Y 1 to Y 12 which are not condensed with the ring represented by Formula 2 to form a condensed ring, are the same or different from each other, and each independently N or C (R 1 );
  • Y 13 to Y 16 When there are a plurality of Y 13 to Y 16 , they are the same as or different from each other, and the Y 13 to Y 16 are each independently N or C (R 1 );
  • each R 1 is independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , 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 boron group, C 6 ⁇ C 60 Aryl phosphine group Or a C 6 -C 60 mono or diarylphosphinyl group and C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
  • Ar 1 to Ar 5 is independently hydrogen, C alkyl group of 1 ⁇ C 40, a cycloalkyl group of C 3 ⁇ C 40, nuclear atomic 3 To 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C 1 to C 40 alkyl silyl group, C 6 ⁇ C 60 aryl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ mono or diaryl phosphine of C 60 blood group and a C 6 ⁇ selected from the group consisting of aryl amine group of C 60, or by combining adjacent groups may form a condensed ring;
  • the phosphine group, mono or diarylphosphinyl group and arylamine group are each independently deuterium, halogen, cyano, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, or 3 to 40 heterocycloheteroatoms Alkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 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
  • the compound represented by the formula (1) has a higher molecular weight than the conventional organic EL device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), the glass transition The temperature is high, not only excellent in thermal stability, but also excellent in carrier transport ability, light emitting ability, and the like. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage of the device is lowered, efficiency and lifespan may be improved.
  • the conventional organic EL device material for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved.
  • the compound of Formula 1 has a triplet energy of 2.3 eV or more.
  • the compound represented by the formula (1) can be adjusted higher than the dopant by introducing a specific substituent on the basic skeleton condensed with a broad singlet energy level and indole derivative having a high triplet energy level Can be used as host material.
  • the compound of the present invention since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transport layer or the hole transport layer adjacent to the light emitting layer. Therefore, when the organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, the exciton is prevented from being diffused by the compound, and thus the first exciton is diffused. Unlike conventional organic electroluminescent devices that do not include a barrier layer, the number of excitons that substantially contribute to light emission in the light emitting layer may be increased, thereby improving the luminous efficiency of the device.
  • the compound represented by Chemical Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material other than the host of the light emitting layer.
  • the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport.
  • EWG electron-withdrawing electron
  • the compound is bonded to an electron-withdrawing electron (EWG) having a high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron.
  • EWG electron-withdrawing electron
  • the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used.
  • an electron donor group EWG
  • the hole injection and transport is smooth.
  • it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
  • the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics.
  • the compound of formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / injection layer Material, light emitting auxiliary layer material, life improving layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, and life improving layer material.
  • the compound of Formula 1 has a variety of substituents, especially aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby conventional light emission It may have a higher thermal stability than the material (eg CBP).
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.
  • the compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas M-1 to M-12.
  • X 1 is selected from the group consisting of O, S and N (Ar 1 ), X 2 may be N (Ar 1 ).
  • Y 1 to Y 16 may be the same as or different from each other, and all may be C (R 1 ) or include 1 to 3 N, wherein a plurality of R 1 are the same or different.
  • the compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas N-1 to N-12.
  • X 1 may be selected from the group consisting of O, S, and N (Ar 1 ).
  • the compound represented by Formula 1 may be characterized in that the compound represented by any one of the following formula (3) to (7).
  • Ar 1 is each independently hydrogen, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, or a nuclear atom having 3 to 40 heterocycloalkyl groups.
  • C 6 ⁇ C 60 aryl group 5 to 60 heteroaryl group of nuclear atoms, 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 boron group, C 6 ⁇ C 60 Aryl phosphine group, C 6 ⁇ C 60 Mono or dia Can be selected from the group consisting of arylphosphinyl group and C 6 -C 60 arylamine group, or can be combined with adjacent groups to form a condensed ring;
  • Y 1 to Y 12 are the same as or different from each other, and each independently N or C (R 1 );
  • Y 13 to Y 16 When there are a plurality of Y 13 to Y 16 , they are the same as or different from each other, and the Y 13 to Y 16 are each independently N or C (R 1 );
  • each R 1 is independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , 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 boron group, C 6 ⁇ C 60 Aryl phosphine group Or a C 6 -C 60 mono or diarylphosphinyl group and C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
  • a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, a mono or diaryl phosphine blood group and the arylamine groups are each independently selected from deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ aryl si
  • Ar 1 may be an aryl group of C 6 to C 60 , and in particular, when Ar 1 is a plurality, at least one may be an aryl group of C 6 to C 60 , wherein The aryl group may be unsubstituted or substituted with one or more C 6 -C 60 aryl groups, and when substituted with a plurality of substituents, they may be the same or different from each other.
  • Y 8 is C (R 1 ), and R 1 may be an aryl group of C 6 to C 60 , more preferably a phenyl group.
  • At least one of Y 1 to Y 12 that does not form a condensed ring with the ring represented by the formula (2) is C (R 1 )
  • at least one of the R 1 is a phenyl group Can be.
  • At least one of R 1 and Ar 1 to Ar 5 may be a phenyl group or a substituent represented by the following formula (8).
  • L 1 is selected from the group consisting of a single bond, a C 6 ⁇ C 18 arylene group and a nuclear atoms of 5 to 18 groups heteroarylene, preferably a single bond, phenylene group, biphenyl group or a carbazolyl group;
  • Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 11 ), wherein at least one of Z 1 to Z 5 is N;
  • R 11 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 3 C 40 -cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 arylamine group, C 1 -C 40 alkylsilyl group, C 1 -C 40 alkylboron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 mono or diaryl the Phosphinicosuccinic
  • An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R 11 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, An aryl phosphine group, a mono or diaryl phosphinyl group and an aryl silyl group, the arylene group and hetero arylene group of L 1 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 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ aryloxy C 60, C 1 ⁇
  • the substituent represented by Formula 8 may be a substituent represented by any one of the following O-1 to O-15.
  • n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R 12 , and when n is an integer of 1 to 4, R 12 is each independently deuterium, halogen, cyan No group, nitro 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, nuclear atom of 3 to 40 heterocycloalkyl group , C 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl group of nuclear atoms, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 arylamine group , C 1 ⁇ C 40 Alkylsilyl 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
  • the arylphosphine group, mono or diarylphosphinyl group and arylsilyl group 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 6 ⁇ C 60 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 An arylamine group, a C 3 to C 40 cycl
  • L 1 and R 11 are each as defined in Chemical Formula 8 above.
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently may be selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, biphenyl and quinazoline,
  • Phenyl, pyridine, pyrimidine, triazine, biphenyl, and quinazoline of Ar 1 to Ar 5 may be one or more selected from the group consisting of cyano, phenyl, pyridine, pyrimidine, triazine, biphenyl, and quinazoline Substituted or unsubstituted, when substituted with a plurality of substituents, they may be the same or different from each other.
  • the compound represented by Formula 1 of the present invention may be represented by the following structure in more detail with the following compounds, but is not limited thereto.
  • the compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device includes (i) an anode, (ii) a cathode and (iii) one or more organic material layers interposed between the anode and the cathode. At least one of the one or more organic material layers includes a compound represented by Chemical Formula 1. In this case, the compound may be used alone, or two or more kinds thereof may be mixed and used.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 It may include a compound represented.
  • the organic material layer including the compound of Formula 1 is preferably selected from the group consisting of a light emitting layer, an electron transport layer and a hole transport layer, more preferably may be a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.
  • the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • an electron injection layer may be further stacked on the electron transport layer, and as described above, at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer may be represented by Chemical Formula 1 It may include a compound.
  • the organic electroluminescent device may include a life improvement layer or an electron transport auxiliary layer between the light emitting layer and the electron transport layer.
  • the compound represented by Chemical Formula 1 may also be used as a life improvement layer or an electron transport auxiliary layer.
  • the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.
  • the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • 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.
  • the substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • 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), 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), 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
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
  • 6-phenyl-6,10b-dihydro-1aH-dibenzo [b, f] oxyreno [2,3-d] azepine (84.0 g, 294.3 mmol), lithium iodine (47.3 g, 353.2 mmol) under nitrogen stream ) And chloroform (840 ml) were mixed and stirred at 60 ° C. for 1 hour.
  • 6-phenyl-6,12b-dihydro-1aH-benzo [f] naphtho [1,2-b] oxyreno [2,3-d] azepine (60.9 g, 181.7 mmol) under nitrogen stream, lithium iodine (29.2 g, 218.0 mmol) and chloroform (600 ml) were mixed and stirred at 60 ° C. for 1 hour.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / 90% of the host compound + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30)
  • An organic EL device was fabricated by laminating in order of nm) / LiF (1 nm) / Al (200 nm).
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound A-1 as a light emitting host material when forming the emission layer.
  • Example 1 A-1 6.77 517 41.3
  • Example 2 A-2 6.46 515 41.3
  • Example 3 A-3 6.81 518 39.7
  • Example 4 A-4 6.68 518 38.9
  • Example 5 A-5 6.66 517 41.5
  • Example 6 A-6 6.48 518 39.2
  • Example 7 A-7 6.48 517 41.3
  • Example 8 A-9 6.86 515 39.7
  • Example 9 A-10 6.48 518 38.9
  • Example 11 B-2 6.86 517 41.3
  • Example 12 B-3 6.77 515 41.3
  • Example 14 B-5 6.65 518 38.9
  • Example 15 -6 6.65 517 41.3
  • Example 16 B-7 6.64 515 41.3
  • Example 17 B-9 6.64 518 41.3
  • Example 18 B-10 6.64 518 41.2
  • Example 19 C-1 6.81 517 42.2
  • Example 20 C-2 6.66 515 42
  • Example 21 C-3 6.81 518 39.7
  • the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / 90% host compound of Table 2 + 10% (piq) 2 Ir (acac) (300nm) / BCP (10 nm) / Alq
  • An organic electroluminescent device was manufactured by stacking 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.
  • a red organic electroluminescent device was manufactured in the same manner as in Example 55, except for using CBP instead of Compound A-8 of Synthesis Example 8 as a light emitting host material when forming the emission layer.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and the substrate was cleaned for 5 minutes using UV. The substrate was then transferred to a vacuum depositor.
  • ITO Indium tin oxide
  • DS-H522 and DS-501 used in device fabrication are products of Doosan Electronics BG, and the structures of m-MTDATA, TCTA, CBP, Ir (ppy) 3 , and BCP are as follows.
  • Example 61 Except for using the compound B-9, C-9, D-9, E-9, F-9 synthesized in place of the compound A-9 used as the hole transport layer material in forming the hole transport layer in Example 61, The organic EL device was fabricated in the same manner as in Example 61.
  • An organic EL device was manufactured in the same manner as in Example 61, except that NPB was used as the hole transport layer material instead of Compound A-9 used as the hole transport layer material when forming the hole transport layer in Example 61.
  • the structure of the NPB used is as follows.
  • the organic EL device (the organic EL device manufactured in each of Examples 61 to 66) using the compounds (A-9 to F-9) according to the present invention as a hole transporting layer, Compared with the organic EL device (organic EL device of Comparative Example 3), it was found that the device exhibited better performance in terms of current efficiency and driving voltage.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • a blue organic EL device was manufactured in the same manner as in Example 67, except that each compound shown in Table 4 was used instead of the compound A-1 used as the life improving layer material in Example 67.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 67, except that Alq 3 , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm without including the life improving layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that instead of using Compound A-1 used as the life improving layer material in Example 67, BCP was used.
  • the structure of the BCP used at this time is as follows.
  • the blue organic EL devices of Examples 67 to 108 are not only excellent in driving voltage and current efficiency, but also have a long life compared to the blue organic EL devices of Comparative Example 5, which use CBP as the hole blocking layer material instead of the life improvement layer. Has been improved.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • a blue organic EL device was manufactured in the same manner as in Example 109, except that each compound shown in Table 5 was used instead of Compound A-5 used as the electron transporting layer material in Example 109.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 108, except that Alq 3 , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm without including the life improving layer.
  • the compound of Formula 1 according to the present invention when used as the life improving layer material or the electron transporting layer material, it was confirmed that the driving voltage and the current efficiency were improved, and further, the life characteristics could be greatly improved.
  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel organic compound having excellent hole injection and transporting ability, electron injection and transporting ability, light emitting ability, and the like, to one or more organic material layers.
  • the present invention relates to an organic EL device having improved characteristics such as high luminous efficiency, low driving voltage and lifetime.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)

Abstract

La présente invention concerne un nouveau composé ayant une excellente capacité d'émission de lumière, et un élément électroluminescent organique ayant des caractéristiques, telles qu'une efficience lumineuse élevée, une faible tension d'excitation, et une longue durée de vie, du fait qu'elle contient le nouveau composé dans au moins une couche de matériau organique.
PCT/KR2016/000780 2015-01-26 2016-01-25 Composé organique électroluminescent, et élément organique électroluminescent l'utilisant Ceased WO2016122178A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020150012223A KR102307239B1 (ko) 2015-01-26 2015-01-26 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR10-2015-0012223 2015-01-26

Publications (3)

Publication Number Publication Date
WO2016122178A2 WO2016122178A2 (fr) 2016-08-04
WO2016122178A3 WO2016122178A3 (fr) 2016-10-06
WO2016122178A9 true WO2016122178A9 (fr) 2016-12-29

Family

ID=56544500

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2016/000780 Ceased WO2016122178A2 (fr) 2015-01-26 2016-01-25 Composé organique électroluminescent, et élément organique électroluminescent l'utilisant

Country Status (2)

Country Link
KR (1) KR102307239B1 (fr)
WO (1) WO2016122178A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170075122A (ko) * 2015-12-22 2017-07-03 삼성디스플레이 주식회사 유기 발광 소자
KR102579752B1 (ko) 2015-12-22 2023-09-19 삼성디스플레이 주식회사 유기 발광 소자
KR20170075114A (ko) 2015-12-22 2017-07-03 삼성디스플레이 주식회사 유기 발광 소자
KR102673509B1 (ko) * 2016-09-28 2024-06-10 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102656921B1 (ko) * 2016-12-20 2024-04-16 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102207894B1 (ko) * 2018-03-30 2021-01-26 삼성에스디아이 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110008619A (ko) * 2009-07-20 2011-01-27 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR101667099B1 (ko) * 2013-03-29 2016-10-17 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR101641404B1 (ko) * 2013-12-17 2016-07-20 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자

Also Published As

Publication number Publication date
KR102307239B1 (ko) 2021-10-01
WO2016122178A2 (fr) 2016-08-04
WO2016122178A3 (fr) 2016-10-06
KR20160091735A (ko) 2016-08-03

Similar Documents

Publication Publication Date Title
WO2016089080A1 (fr) Composé luminescent organique et dispositif électroluminescent organique comprenant un tel composé
WO2016105165A2 (fr) Composé électroluminescent organique et dispositif électroluminescent organique l'utilisant
WO2015190718A1 (fr) Dispositif électroluminescent organique
WO2018038401A1 (fr) Composé organique et dispositif à électroluminescence organique comprenant un tel composé
WO2014010810A1 (fr) Nouveau composé et dispositif électroluminescent le comprenant
WO2020159019A1 (fr) Composé électroluminescent organique, et dispositif électroluminescent organique l'utilisant
WO2020209679A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2018038400A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2017209488A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2019004584A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2017111544A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2016105054A2 (fr) Composé organique luminescent et élément électroluminescent organique faisant appel audit composé
WO2019103397A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2015111864A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2015133804A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2022005249A1 (fr) Composé organique et dispositif électroluminescent organique l'utilisant
WO2018038464A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2016122178A9 (fr) Composé organique électroluminescent, et élément organique électroluminescent l'utilisant
WO2015111943A1 (fr) Composé organique et dispositif électroluminescent organique le contenant
WO2015133808A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2017095086A1 (fr) Composé organique d'émission de lumière et dispositif organique électroluminescent l'utilisant
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2017111389A1 (fr) Composé organique et diode électroluminescente organique comprenant ledit composé
WO2014081131A1 (fr) Composé organique et son dispositif organique électroluminescent

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16743656

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205N DATED 04.10.2017)

122 Ep: pct application non-entry in european phase

Ref document number: 16743656

Country of ref document: EP

Kind code of ref document: A2