WO2015060635A1 - Composé organique et élément organique électroluminescent le comprenant - Google Patents

Composé organique et élément organique électroluminescent le comprenant Download PDF

Info

Publication number
WO2015060635A1
WO2015060635A1 PCT/KR2014/009937 KR2014009937W WO2015060635A1 WO 2015060635 A1 WO2015060635 A1 WO 2015060635A1 KR 2014009937 W KR2014009937 W KR 2014009937W WO 2015060635 A1 WO2015060635 A1 WO 2015060635A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
aryl
formula
Prior art date
Application number
PCT/KR2014/009937
Other languages
English (en)
Korean (ko)
Inventor
김성무
이용환
박호철
이창준
신진용
백영미
김태형
라종규
Original Assignee
주식회사 두산
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 주식회사 두산 filed Critical 주식회사 두산
Publication of WO2015060635A1 publication Critical patent/WO2015060635A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • 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
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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
    • H10K85/114—Poly-phenylenevinylene; Derivatives thereof
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a novel organic compound that can be used as a material of the organic electroluminescent device and to an organic electroluminescent device in which the luminous efficiency, driving voltage, lifespan, etc. of the device are improved.
  • 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 material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color.
  • a host / dopant system may be used as a light emitting material.
  • 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.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp).
  • Metal complex compounds containing Ir, such as 2 are used.
  • 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.
  • An object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and capable of improving the bonding force between holes and electrons.
  • an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.
  • the present invention provides a compound represented by Formula 1:
  • Ar 1 is a substituent represented by the following formula (2);
  • L is a single bond, a substituted or unsubstituted C 6 -C 40 arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;
  • X 1 to X 5 are the same as or different from each other, each independently N or C (R 11 ), and include at least one N,
  • R 11 when two or more of X 1 to X 5 is C (R 11 ), a plurality of R 11 are the same or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C 1 ⁇ C 40 alkyl group, substituted or unsubstituted C 6 ⁇ C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryl Oxy group, substituted or unsubstituted C 1 -C 40 alkyloxy group, substituted or unsubstituted C 6 -C 40 arylamine group, substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or Unsubstituted C 1 to C 40 alkylboron group, substituted or unsubstituted C 6 to C 40 arylboron group, substituted or unsubsti
  • R 1 to R 3 are the same as or different from each other, and each independently deuterium (D), halogen, cyano, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkene Nyl group, substituted or unsubstituted C 2 to C 40 alkynyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryloxy group, substituted or unsubstituted C 1 ⁇ C 40 Alkyloxy group, substituted or unsubstituted C 6 ⁇ C 40 arylamine group, substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 3 to 40 nuclear atoms, substituted or unsub
  • R 1, R 2 and R 3 when present is a plurality of, respectively, a plurality of R 1, R 2 and R 3 are the same or different from each other,
  • a, b and c are each independently an integer of 0-5,
  • R 1 to R 3 and R 11 C 6 ⁇ C 40 arylene group, a heteroarylene group of 5 to 40 nuclear atoms, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkylboron group, C group of 6 to arylboronic of C 40, C 6 to C 40 aryl phosphine group, C 6 to C 40 aryl phosphine oxide group, and a C 6 to an aryl silyl group of C 40, each independently selected from deuterium,
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, at least one of the one or more organic material layers is an organic electric field characterized in that it comprises a compound of the formula (1) Provided is a light emitting device.
  • At least one of the one or more organic material layers including the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer, it is preferable that the light emitting layer.
  • the compound represented by Formula 1 may be a green or red phosphorescent host material.
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability and phosphorescence properties, it may be used as a material of the organic material layer of the organic EL device.
  • the compound represented by Chemical Formula 1 according to the present invention when used as a phosphorescent host material, 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 significantly improved performance and lifetime can also be manufactured.
  • the novel compound according to the present invention forms a basic skeleton with a carbozole moiety in which phenyl is bonded at positions 1 and 3, and various substituents are bonded to the basic skeleton, represented by Chemical Formula 1 It is characterized by.
  • a carbazole moiety is used as an organic electroluminescent device material, especially as a phosphorescent host material. It is used in various ways.
  • the carbazole moiety has a high triplet energy of 3.0 eV and a low HOMO energy level of 6.0 eV, which is mainly used in blue phosphorescent hosts.
  • the present invention is characterized in that the electron withdrawing group (EWG) represented by the formula (2) is substituted in position 9 of the 1,3-diphenyl-9H-carbazole structure.
  • the structure having both electron withdrawing group (EWG) and electron donating group (EDG) with high electron donor has a bipolar characteristic, so that the whole molecule has a bipolar characteristic. Since it can be increased, not only is it advantageous as a host in the phosphorescent light emitting layer, but also can be applied as a hole transporting layer, a hole injection layer and the like.
  • a phenyl group substituted at the position 1 of the carbazole moiety and an electron withdrawing group (EWG) substituted at the position 9 at the carbazole moiety are adjacent to each other to cause steric hinderance. Therefore, the compound molecules are distorted to solve the problem of deterioration of the luminescence property due to ⁇ - ⁇ -stacking, thereby preventing the formation of excitation dimers (eximers), thereby improving the luminescence efficiency. do.
  • the host material requires that the triplet energy gap of the host is higher than that of the dopant because the lowest excited state of the host must be higher than the lowest emission state of the dopant in order to provide effective phosphorescence from the dopant.
  • the novel compound according to the present invention is lower than the triplet energy of the compound having a simple carbazole moiety as a basic skeleton by phenyl substitution at positions 1 and 3 of the carbazole moiety, and is suitable for green phosphorescence emission. It can have
  • the compound represented by Formula 1 of the present invention is a molecular weight of the compound is significantly increased due to the aromatic ring (aromatic ring) or heteroaromatic ring (substituents) substituents introduced in the molecule, so that the glass transition temperature is conventionally improved It shows higher thermal stability than CBP (4,4-dicarbazolybiphenyl).
  • the compound represented by the formula (1) of the present invention is also effective in suppressing the crystallization of the organic material layer.
  • a ceramic crucible having high thermal conductivity is used as a method of forming an organic layer of an organic light emitting device by vacuum deposition, and should be designed so that stepwise continuous evaporation control is possible and no organic splashing occurs.
  • the temperature of the evaporation source is not properly raised, the organic material that reaches the evaporation temperature in an excessively short time is splashed, and the inlet of the evaporation source is blocked, and thus the deposition rate of the organic material is not constant and thus the desired thin film characteristics are not obtained. . It also increases the likelihood that organic matter will discolor or decolorize during deposition.
  • the organic material has the property of being deposited by melting or sublimation depending on the material.
  • the compound In the case of the sublimation method, the compound immediately forms a organic layer through a sublimation process in the solid state, whereas in the melting method, the solid passes through a liquid. Vaporize to form an organic layer. Melting method is difficult to control the deposition temperature or uniformity because the material undergoes a phase change one step more than the sublimation method.
  • 1,3-diphenyl-9H-carbazole structure is deposited by the sublimation method
  • the compound of the present invention can have uniform thin film properties, thereby improving the luminescence properties.
  • the compound of Formula 1 according to the present invention when used as a hole injection / transport layer material of an organic electroluminescent device or a phosphorescent host material of blue, green and / or red color, it is compared with conventional organic material layers (for example, CBP).
  • organic material layers for example, CBP.
  • the efficiency and lifespan of the organic electroluminescent device can be greatly improved.
  • the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • the novel compound according to the present invention has a structure in which a substituent represented by formula (2) is bonded to a carbazole moiety basic skeleton of formula (1) in which phenyl is bonded to positions 1 and 3, respectively.
  • Ar 1 introduced at the N site of the carbazole basic skeleton may be embodied as in Chemical Formula 2.
  • L is a linker of a divalent group known in the art, a single bond, a substituted or unsubstituted C 6 ⁇ C 40 arylene group, and a substituted or unsubstituted nuclear atom It may be selected from the group consisting of 5 to 40 heteroarylene groups.
  • examples of the C 6 to C 40 arylene group and the heteroarylene group having 5 to 40 nuclear atoms include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, and a pyrantrenylene group , Carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group, pyrimididi Nylene groups and the like.
  • L is preferably selected from a single bond, a phenylene group, or a biphenylene group.
  • C 6 ⁇ C 40 arylene group, a heteroarylene group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group , C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 Alkylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 with an aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide
  • X 1 to X 5 are the same as or different from each other, and each independently N or C (R 11 ), and include at least one N.
  • R 11 when two or more of X 1 to X 5 are C (R 11 ), a plurality of R 11 may be the same or different from each other even though they are the same, and each independently hydrogen, deuterium (D), halogen, cyano group, substitution or Unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 aryloxy group, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine group, substituted or unsubstituted C 1 to C 40 alkylsilyl group , Substituted or unsubstituted C 1 ⁇ C 40 alkyl boron group, substituted or unsubstituted C 6 ⁇ C 40 aryl boron
  • the groups are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 To 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl of the group, C 1
  • the substituent represented by Formula 2 may be a substituent represented by any one of the following formulas A-1 to A-15.
  • R 21 is hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C 1 -C 40 alkyl group, substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted nuclear atom 5 to 40 heteroaryl groups, substituted or unsubstituted C 6 to C 40 aryloxy groups, substituted or unsubstituted C 1 to C 40 alkyloxy groups, substituted or unsubstituted C 6 to C 40 aryl An amine group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 1 to C 40 alkylboron group, a substituted or unsubstituted C 6 to C 40 aryl boron group, substituted or aryl phosphonium the unsubstituted C 6 ⁇ C 40 pingi, a substituted or unsubstituted C 6
  • n is an integer of 0-4.
  • the groups are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 To 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl of the group, C 1
  • substituents represented by Formulas A-1 to A-15 are preferably selected from the group of substituents represented by the following structures. However, this is not particularly limited.
  • R 1 to R 3 are the same or different, and each independently deuterium (D), halogen, cyano, alkyl group of C 1 ⁇ C 40 , C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyl Oxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, is selected from the group consisting of C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group, and a C 6 ⁇ with
  • arylsilyl groups are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, nucleus A heterocycloalkyl group having 3 to 40 atoms, a
  • each of R 1 to R 3 is preferably a C 6 to C 40 aryl group, more preferably a phenyl group.
  • a, b, and c are each independently an integer of 0-5.
  • the compound represented by Chemical Formula 1 may be further embodied as a compound represented by any one of the following Chemical Formulas 3 to 7.
  • Ar 1 is the same as defined in Formula 2, and each Ar 1 is the same or different,
  • Z 1 is selected from O, S, Se, N (R 4 ), C (R 5 ) (R 6 ) and Si (R 7 ) (R 8 )
  • R 4 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 aryloxy group, substituted or unsubstituted C 1 to C 40 alkyloxy group , Substituted or unsubstituted C 6 -C 40 arylamine group, substituted or unsubstituted C 1 -C 40 alkylsilyl group, substituted or unsubstituted C 1 -C 40 alkylboron group, substituted or unsubstituted C 6 ⁇ C 40 aryl boron group, substituted or unsubstituted C 6 ⁇ C 40 aryl phosphine group, substitute
  • R 4 to R 8 are the same as or different from each other, and each independently a C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted nuclear atom 5 to 5 It is preferably selected from 40 heteroaryl groups.
  • arylsilyl groups are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, nucleus A heterocycloalkyl group having 3 to 40 atoms, a
  • the compound represented by Chemical Formula 1 of the present invention described above may be further embodied in a compound structure consisting of C-1 to C-168 illustrated below.
  • the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds, and examples thereof include ethynyl. , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, singly or in combination of two or more rings.
  • a form in which two or more rings are pendant or condensed with each other may also be included.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention 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 simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 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 1 to 40 alkyl, and is linear, branched or cyclic structure.
  • 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 in the present invention means 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, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or 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 40 carbon atoms
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the compound of formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.
  • the organic electroluminescent device comprises an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone, or two or more may be used in combination.
  • 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 layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1).
  • the organic material layer including the compound of Formula 1 may be a light emitting layer.
  • the light emitting layer of the organic electroluminescent device may include a host material, wherein the host material may include the compound of formula (1).
  • the compound of Formula 1 when included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved.
  • the compound represented by Chemical Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.
  • the structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be.
  • the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer.
  • An electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic 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.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • non-limiting furnaces of the positive electrode material usable 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-methyl
  • non-limiting examples of the negative electrode material that can be used include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.
  • 6-bromo-1,3-diphenyl-9H-carbazole (18.4 g, 46.2 mmol), iodobenzene (14.1 g, 69.3 mmol), Cu powder (0.29 g, 4.62 mmol), K 2 CO 3 (6.38 g) under nitrogen stream , 46.2 mmol), Na 2 SO 4 (6.56 g, 46.2 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C. for 12 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent in the organic layer was removed from water and purified by column chromatography to give 6-bromo-1,3,9-triphenyl-9H-carbazole (15.6 g, 71% yield).
  • PCZ-1 (3.19 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol), NaH (0.24 g, 10.00 mmol) and DMF under nitrogen stream 50 ml) were mixed and stirred at room temperature for 1 hour. After the reaction was completed, water was added and the solid compound was filtered and purified by column chromatography to obtain the title compound C-10 (5.01 g, yield 91%).
  • PCZ-1 (3.19 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (under nitrogen stream 0.46 g, 0.5 mmol), (t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-12 (4.95 g, yield 79%).
  • BCZ-1 (7.13 g, 10.00 mmol), 2-chloro-4,6-diphenylpyridine (3.19 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), (t-Bu) under nitrogen stream 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound C-117 (7.07 g, yield 75%) by column chromatography.
  • BCZ-2 (.61 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 13 to obtain the target compound C-129 (5.53 g, yield 70%).
  • 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
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP and Ref-1 were used as emission host materials in forming the emission layer.
  • Ref-1 The structure of Ref-1 used is as follows.
  • Example 1 C-10 6.64 517 40.8
  • Example 2 C-12 6.57 517 40.9
  • Example 3 C-16 6.46 518 41.9
  • Example 4 C-28 6.51 518 41.1
  • Example 5 C-66 6.51 518 41.1
  • Example 6 C-68 6.59 517 41.7
  • Example 7 C-94 6.65 518 40.1
  • Example 8 C-96 6.49 518 41.9
  • Example 9 C-99 6.59 518 41.5
  • Example 10 C-117 6.50 519 40.6
  • Example 11 C-120 6.60 517 41.8
  • Example 12 C-122 6.55 517 40.9
  • Example 13 C-123 6.44 516 41.3
  • Example 14 C-124 6.50 518 41.5
  • Example 15 C-129 6.45 518 41.5
  • Example 16 C-132 6.50 519 41.9
  • Example 18 C-135 6.45 517 40.5
  • Example 19 C-136 6.55 518 41.5
  • Example 20 C-144 6.60 517 41.8
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then washed the substrate for 5 minutes using UV and vacuum The substrate was transferred to the evaporator.
  • ITO Indium tin oxide
  • M-MTDATA 60 nm) / TCTA (80 nm) / C-25, C-26, C-27 compound + 10% (piq) 2 Ir (acac) (30nm) / BCP ( 10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated to fabricate an organic EL device.
  • a red organic EL device was manufactured in the same manner as in Example 26, except that CBP was used as the emission host material in forming the emission layer.
  • the organic electroluminescent device of Examples 26 to 28 using the compound according to the present invention as a material of the light emitting layer of the red organic electroluminescent device is a red color of Comparative Example 3 using the conventional CBP as a material of the light emitting layer Compared with the organic electroluminescent device, it was found to exhibit excellent performance in terms of efficiency and driving voltage.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique le contenant. Le composé, selon la présente invention, est utilisé dans une couche organique, de préférence dans une couche émettrice de lumière, de l'élément organique électroluminescent, ce qui permet d'améliorer l'efficacité d'émission de lumière, la tension d'attaque, la durée de vie et similaire de l'élément organique électroluminescent.
PCT/KR2014/009937 2013-10-25 2014-10-22 Composé organique et élément organique électroluminescent le comprenant WO2015060635A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020130127817A KR101614583B1 (ko) 2013-10-25 2013-10-25 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2013-0127817 2013-10-25

Publications (1)

Publication Number Publication Date
WO2015060635A1 true WO2015060635A1 (fr) 2015-04-30

Family

ID=52993160

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/009937 WO2015060635A1 (fr) 2013-10-25 2014-10-22 Composé organique et élément organique électroluminescent le comprenant

Country Status (2)

Country Link
KR (1) KR101614583B1 (fr)
WO (1) WO2015060635A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102197612B1 (ko) * 2014-12-22 2021-01-04 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102430017B1 (ko) * 2015-10-28 2022-08-08 엘티소재주식회사 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR102587380B1 (ko) * 2015-12-10 2023-10-12 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102587381B1 (ko) * 2015-12-21 2023-10-12 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN110452226B (zh) * 2019-08-05 2022-04-22 北京大学深圳研究生院 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件
CN114957094A (zh) * 2022-06-09 2022-08-30 北京八亿时空液晶科技股份有限公司 一种多取代咔唑衍生物及其应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020107405A1 (en) * 2000-11-22 2002-08-08 Lin Jiann T?Apos;Suen 3,6,9-Trisubstituted carbazoles for light emitting diodes
JP2005093159A (ja) * 2003-09-16 2005-04-07 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR20110043342A (ko) * 2009-10-21 2011-04-27 제일모직주식회사 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
JP2012169325A (ja) * 2011-02-10 2012-09-06 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR20130094222A (ko) * 2010-06-24 2013-08-23 도레이 카부시키가이샤 발광 소자 재료 및 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020107405A1 (en) * 2000-11-22 2002-08-08 Lin Jiann T?Apos;Suen 3,6,9-Trisubstituted carbazoles for light emitting diodes
JP2005093159A (ja) * 2003-09-16 2005-04-07 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR20110043342A (ko) * 2009-10-21 2011-04-27 제일모직주식회사 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
KR20130094222A (ko) * 2010-06-24 2013-08-23 도레이 카부시키가이샤 발광 소자 재료 및 발광 소자
JP2012169325A (ja) * 2011-02-10 2012-09-06 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置

Also Published As

Publication number Publication date
KR20150047841A (ko) 2015-05-06
KR101614583B1 (ko) 2016-04-21

Similar Documents

Publication Publication Date Title
WO2016105161A2 (fr) Composé organique et élément électroluminescent organique comprenant ce composé
WO2019017616A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique l'utilisant
WO2015060684A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2018230782A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2017003009A1 (fr) Composé émettant de la lumière organique et dispositif électroluminescent organique l'utilisant
WO2015122711A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2017111544A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2015133804A1 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2017209488A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2014098447A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2017111543A1 (fr) Composé organique et dispositif électroluminescent organique comprenant ce composé
WO2015060635A1 (fr) Composé organique et élément organique électroluminescent le comprenant
WO2013168927A2 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2016105123A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2020116881A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2013191355A1 (fr) Nouveau composé et élément électroluminescent organique le comprenant
WO2017095086A1 (fr) Composé organique d'émission de lumière et dispositif organique électroluminescent l'utilisant
WO2020218680A1 (fr) Composé organique et diode électroluminescente organique l'utilisant
WO2016013894A2 (fr) Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2018186551A1 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2015046982A2 (fr) Composé organique et élément électroluminescent organique le contenant
WO2015099477A2 (fr) Nouveau composé organique et dispositif électroluminescent organique l'utilisant
WO2020130725A1 (fr) Composé organique et dispositif électroluminescent organique le comprenant
WO2016105072A2 (fr) Composé organique et élément électroluminescent organique le comprenant
WO2022005247A1 (fr) Composé organique et élément électroluminescent organique l'utilisant

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: 14855911

Country of ref document: EP

Kind code of ref document: A1

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 1205A DATED 05/08/2016)

122 Ep: pct application non-entry in european phase

Ref document number: 14855911

Country of ref document: EP

Kind code of ref document: A1