WO2016105072A2 - Composé organique et élément électroluminescent organique le comprenant - Google Patents

Composé organique et élément électroluminescent organique le comprenant Download PDF

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WO2016105072A2
WO2016105072A2 PCT/KR2015/014077 KR2015014077W WO2016105072A2 WO 2016105072 A2 WO2016105072 A2 WO 2016105072A2 KR 2015014077 W KR2015014077 W KR 2015014077W WO 2016105072 A2 WO2016105072 A2 WO 2016105072A2
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group
aryl
alkyl
compound
boron
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Korean (ko)
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WO2016105072A3 (fr
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이주형
김충한
최태진
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주식회사 두산
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Publication of WO2016105072A3 publication Critical patent/WO2016105072A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • 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.
  • hole injection materials hole transport materials.
  • NPB, BCP, Alq 3 and the like are known as hole blocking materials and electron transporting materials, and metals containing Ir such as anthracene derivatives, Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, etc.
  • Ir such as anthracene derivatives, Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, etc.
  • Complex compounds and the like are known.
  • An object of the present invention is to provide a novel organic compound capable of increasing the hole injection ability, hole transporting ability, light emitting ability, and the like of the organic electroluminescent device.
  • Another object of the present invention is to provide an organic electroluminescent device comprising the novel organic compound.
  • 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 to X 3 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 ), wherein X 1 to X At least one of 3 is N (Ar 1 ),
  • Y 1 to Y 8 are each independently N or C (R 9 ),
  • R 1 to R 8 and R 9 except for forming a condensed ring are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to 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 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 ⁇ C 40 Cycloalkyl group , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to C 60 atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having 1 to C 40 atoms, aryl jade having 6 to C 60 atoms group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ aryl phosphine of C 60 It is selected from the group consisting of a pin group, a C 6 ⁇ C 60 aryl phosphine oxide group and a C 6 ⁇
  • Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 Heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group,
  • 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).
  • alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • Alkenyl in the present invention means 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 in the present invention means 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 means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms 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 thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 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.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, Polycyclic rings such as purinyl, quinolyl, benzothiazole, carbazolyl and 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 1 to 60 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do. Examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples thereof 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, S or Se Is substituted with a hetero atom such as Examples thereof include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 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 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 EL device having excellent light emission performance, driving voltage, and lifespan characteristics may be manufactured, and further, a full color display panel having improved performance and lifespan may also be used. It can manufacture.
  • the organic compound of the present invention is a compound in which benzene and acridine are condensed to an aromatic ring to form a mother nucleus, and various substituents are bonded to the mother nucleus, and are represented by Chemical Formula 1.
  • the compound represented by the formula (1) of the present invention has a variety of substituents are bonded to the mother nucleus significantly increases the molecular weight, the glass transition temperature is improved, it can have a higher thermal stability than conventional light emitting materials (for example, CBP) have.
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer.
  • the compound represented by Formula 1 may have a wide bandgap by adjusting HOMO and LUMO energy levels according to the kind of substituents introduced into the mother nucleus.
  • a mother-containing heterocycle e.g., pyridine group, pyrimidine group, triazine group, etc.
  • EWG electron withdrawing electron
  • the compound represented by Chemical Formula 1 of the present invention when applied to the organic material layer of the organic light emitting device, the light emission characteristics of the organic light emitting device are improved, and the hole injection / transportation capability and the electron injection / transportation capability are improved, thereby driving voltage is increased.
  • An organic electroluminescent device having a low and long life can be provided.
  • Such a compound represented by Formula 1 of the present invention may be embodied in any one of the compounds represented by the following formulas C-1 to C-9.
  • X 1 to X 3 , Y 1 to Y 8 , R 1 , R 3 and R 4 are the same as defined in Chemical Formula 1.
  • At least one of X 1 to X 3 is N (Ar 1 ), and among them, X 3 is preferably N (Ar 1 ).
  • X 1 to X 3 is preferably a combination as shown in Table 1 below, but is not limited thereto.
  • Y 1 to Y 8 are all C (R 9 ), or one of Y 1 to Y 8 is preferably N.
  • Y 1 to Y 8 are all C (R 9 )
  • a plurality of C (R 9 ) are the same as or different from each other.
  • R 9 may be bonded to each other with adjacent R 9 to form a condensed ring.
  • R 1 to R 8 , R 9 and Ar 1 to Ar 5 except for forming a condensed ring At least one (particularly, Ar 1 ) is preferably a substituent represented by the following formula (4).
  • L is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,
  • 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, a plurality of C when C (R 11 ) is a plurality (R 11 ) are the same as or different from each other,
  • R 11 is hydrogen, 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 40 aryl group , nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ aryloxy C 40 C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ⁇ C 40 arylamine 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 aryl phosphine group And, C 6 ⁇ C 40 An aryl phosphine oxide group and C 6 ⁇ C 40 An arylsilyl group selected from the group, or combine with an
  • Substituents represented by Formula 4 may be embodied by any one of the substituents represented by the following A-1 to A-15.
  • R 12 is hydrogen, 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 40 aryl group, of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ⁇ C 40 arylamine 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 aryl phosphine group And, C 6 ⁇ C 40 An aryl phosphine oxide group and C 6 ⁇ C 40 An arylsilyl group selected from the group,
  • the arylphosphine group, the arylphosphine oxide group, and the 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 alky Neyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, an aryl boronic of C 3 ⁇ C 40 cycloal
  • n is an integer of 0-4.
  • At least one (particularly, Ar 1 ) is preferably a substituent represented by the following formula (5).
  • L 2 is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,
  • R 13 and R 14 are each independently a C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C 6 ⁇ selected from the group consisting of an aryl amine of the C 60 Or combine with each other to form a condensed ring,
  • the alkyl group, aryl group, heteroaryl group, and arylamine group of R 13 and R 14 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 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 aryl amine group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group 1 ⁇ C 40 alkyl silyl, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40
  • Specific examples of the compound represented by Chemical Formula 1 of the present invention include, but are not limited to, a compound represented by 1 to 120 below.
  • the core of the compound represented by Chemical Formula 1 of the present invention may be synthesized by, for example, the following reaction scheme, and the synthesis process is specified by Preparation Examples 1 and 2 below.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by the formula (1).
  • the compound may be used alone, or two or more may be used in combination.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a hole barrier 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 a compound represented by Formula 1 It may include.
  • the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer.
  • the emission layer may include a host, wherein the host may include a compound represented by Formula 1 or a compound other than the compound represented by 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.
  • An insulating layer or an adhesive layer may be further inserted at an interface between the anode, the cathode, and the organic material layer.
  • Such an organic electroluminescent device of the present invention may 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 manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like can 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 oxides with metals 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 oxides with metals such as ZnO: Al or SnO 2: Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly
  • 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.
  • a target compound 5.0 g (yield 56%) was obtained in the same manner as in Synthesis Example 10, except that Compound 2 (A), which was synthesized in Preparation Example 2, was used instead of Compound 1 (A).
  • a target compound 5.0 g (yield 57%) was obtained in the same manner as in Synthesis Example 11, except that Compound 2 (A), which was synthesized in Preparation Example 2, was used instead of Compound 1 (A).
  • a target compound 5.0 g (yield 56%) was obtained in the same manner as in Synthesis Example 14, except that 2 (A) compound synthesized in Preparation Example 2 was used instead of 1 (A).
  • a target compound 5.0 g (yield 42%) was obtained in the same manner as in Synthesis Example 16, except that Compound 2 (A), which was synthesized in Preparation Example 2, was used instead of Compound 1 (A).
  • a target compound 4.0 g (yield 43%) was obtained in the same manner as in Synthesis Example 9, except that compound 2 (B) synthesized in Preparation Example 2 was used instead of compound 1 (A).
  • a target compound 5.0 g (yield 56%) was obtained in the same manner as in Synthesis Example 10, except that compound 2 (B) synthesized in Preparation Example 2 was used instead of 1 (A).
  • a target compound 5.0 g (yield 59%) was obtained in the same manner as in Synthesis Example 18, except that Compound 2 (B), which was synthesized in Preparation Example 2, was used instead of Compound 1 (A).
  • the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
  • ITO Indium tin oxide
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / 90% on the ITO transparent substrate (electrode) thus prepared + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) /
  • the device was fabricated by laminating in order of Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
  • a device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound synthesized in Synthesis Example 1 as a host material when forming the emission layer.
  • a device was manufactured in the same manner as in Example 1, except that a PNFC compound synthesized by the following synthesis method was used instead of the compound synthesized in Synthesis Example 1 as a host material when forming the emission layer.

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

Abstract

La présente invention concerne un composé organique et un élément électroluminescent organique présentant des propriétés améliorées, telles que l'efficacité d'émission de lumière, la tension d'attaque et la durée de vie, du fait qu'il comprend ledit composé organique dans une ou plusieurs couches organiques.
PCT/KR2015/014077 2014-12-24 2015-12-22 Composé organique et élément électroluminescent organique le comprenant WO2016105072A2 (fr)

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KR102599413B1 (ko) * 2016-07-11 2023-11-08 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102692891B1 (ko) * 2016-07-15 2024-08-08 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102696702B1 (ko) 2018-09-11 2024-08-22 삼성디스플레이 주식회사 유기 전계 발광 소자 및 유기 전계 발광 소자용 아민 화합물

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