WO2014065501A1 - Composé organique et élément électroluminescent organique comprenant celui-ci - Google Patents

Composé organique et élément électroluminescent organique comprenant celui-ci Download PDF

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WO2014065501A1
WO2014065501A1 PCT/KR2013/007955 KR2013007955W WO2014065501A1 WO 2014065501 A1 WO2014065501 A1 WO 2014065501A1 KR 2013007955 W KR2013007955 W KR 2013007955W WO 2014065501 A1 WO2014065501 A1 WO 2014065501A1
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group
substituted
unsubstituted
aryl
synthesis
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백영미
김성무
이용환
박호철
이창준
신진용
김태형
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주식회사 두산
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Definitions

  • the present invention relates to a novel organic compound which can be used as a material for an organic electroluminescent device, and an organic electroluminescent device in which the luminous efficiency, driving voltage, lifetime, 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 a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission 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 a hole injection layer, a hole transport layer, a hole blocking layer, and an electron transport layer, and anthracene derivatives are reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, and the like. Green and red dopant materials are used, and CBP is a phosphorescent host material.
  • 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 the following formula (1).
  • At least one of R 6 and R 7 or R 7 and R 8 forms a condensed ring with the following Chemical Formula 2,
  • X is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ), Si (Ar 5 ) (Ar 6 ), P (Ar 7 ) and B (Ar 8 ) Obviously,
  • R 1 to R 12 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or Unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 Aryloxy group of -C 60 , substituted or unsubstituted C 1 -C 40 alkylsilyl group
  • Ar 1 to Ar 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 An alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or Unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 Aryloxy group of -C 60 , substituted or unsubstituted C 1 -C 40 alkylsilyl group
  • R 1 to R 12 and Ar 1 to Ar 8 substituents having the term 'substituted or unsubstituted' are described, for example, an alkyl group, an alkenyl group, an alkynyl group, 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, an aryl phosphine oxide group, an arylamine group are each independently deuterium, halogen, cyano group, nitro A group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a nuclear atom having 5 to
  • 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).
  • At least one of the one or more organic material layers may be selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer, it is preferable that the light emitting layer.
  • the compound represented by Chemical Formula 1 is a blue, green or red phosphorescent host material.
  • novel compound represented by Chemical Formula 1 of the present invention is excellent in thermal stability and phosphorescence property, it can be applied to the light emitting layer of the organic EL device.
  • the present invention not only has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], but also has a wide energy band gap to increase the bonding force between holes and electrons. It can be characterized in that it provides a compound represented by the formula (1).
  • the novel compound represented by Chemical Formula 1 has an indole fused to a carbazole basic skeleton, and energy levels are controlled by various substituents, thereby wide bandgap (sky blue ⁇ red).
  • the phosphorescence property of the device may be improved, and the hole injection ability and / or transport capacity, efficiency (luminescence efficiency, power efficiency), driving voltage, lifetime characteristics, luminance, etc. may be improved.
  • the light emitting layer may be applied to a hole transport layer, a hole injection layer, etc. due to the introduction of various substituents.
  • the compound exhibits excellent properties as a host material of the light emitting layer as compared to the conventional CBP, because the compound has a wide bandgap and can enhance the bond strength between holes and electrons due to the structural specificity in which indole groups are fused to the carbazole base skeleton. Can be.
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the carbazole basic skeleton in which the indole group is fused, thereby improving the glass transition temperature, thereby resulting in higher thermal stability than the conventional CBP.
  • the cyclohexyl fused to the inside of a carbazole ring can improve the thermal stability of a compound, and the novel compound of this invention is also effective in the stability of the organic film containing this compound, and the suppression of crystallization. Therefore, the organic EL device containing the compound of the present invention can greatly improve durability and lifespan characteristics.
  • the compound of Formula 1 according to the present invention when adopted as a hole injection / transport layer, blue, green, and / or red phosphorescent host material of an organic EL device, the compound of Formula 1 may have an excellent effect on efficiency and lifetime compared to conventional CBP. have. Therefore, the compound according to the present invention can greatly contribute to the improvement of the performance and the life of the organic EL device, and in particular, the life of the device has a great effect in maximizing the performance in the full color organic light emitting panel.
  • R 1 to R 12 excluding R 6 and R 7 and / or R 7 and R 8 are the same as each other, or Different, each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 -C 40 alkyl group, substituted or unsubstituted C 2 -C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 alkynyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 60 aryl Groups, substituted or unsubstituted heteroaryl groups having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy groups, substituted or
  • R 1 to R 12 excluding R 6 and R 7 and / or R 7 and R 8 are hydrogen, a substituted or unsubstituted C 6 ⁇ C 60 aryl group, substituted or unsubstituted 5 to 5 nuclear atoms It is preferable when it is a heteroaryl group of 60.
  • the dotted line means a site where the condensation is made with the compound of Formula 1.
  • X is O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ), Si (Ar 5 ) (Ar 6 ), P (Ar 7 ) and B ( Ar 8 ), preferably selected from O, S, N (Ar 2 ), C (Ar 3 ) (Ar 4 ), and more preferably N (Ar 2 ).
  • Ar 1 to Ar 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 ⁇ C 40 alkenyl group, a substituted or unsubstituted C 2 ⁇ C 40 of the alkynyl group, a substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 hetero Cycloalkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 -C 40 alkyloxy group, substituted or Unsubstituted C 6 to C 60 aryloxy group, substituted or Unsubstituted C 1 to C 40 al
  • Ar 1 is preferably a substituted or unsubstituted C 6 ⁇ C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms.
  • Ar 2 to Ar 8 is a substituted or unsubstituted C 1 ⁇ C 40 Alkyl group, a substituted or unsubstituted C 6 ⁇ C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms desirable.
  • X is N (Ar 2 )
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 to C 40 aryl group, and a substituted or unsubstituted nucleus. It is preferably selected from the group consisting of heteroaryl groups having 5 to 40 atoms.
  • the C 6 ⁇ C 40 aryl group, the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alke 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 the , 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 6 ⁇ C 40 arylsilyl group , a C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphin
  • R 1 to R 12 , Ar 1 to Ar 8, which are substituents of the compound of formula 1 according to the present invention, are each independently selected from hydrogen or the following substituent (functional group) group, for example, S1 to S192, particularly R 1 to R 12 , Ar 1 and Ar 2 are more preferably selected from hydrogen or the following substituent groups (S1 to S192). However, it is not limited thereto. However, in R 1 to R 12 defined above, substituents forming a condensed ring with Formula 2, for example, R 6 and R 7 and / or R 7 and R 8 are excluded.
  • the compound represented by the formula (1) of the present invention can be more specifically embodied by the compound represented by the formula of any one of formulas (3) to (6).
  • Ar 1 to Ar 8 and R 1 to R 12 are the same as defined in Formula 1, respectively.
  • Ar 1 and Ar 2 are the same as or different from each other, each independently represent a substituted or unsubstituted C 6 ⁇ C 40 aryl group, and a substituted or unsubstituted Selected from the group consisting of heteroaryl groups having 5 to 40 nuclear atoms,
  • R 1 to R 12 are the same as or identical to each other, and are each independently selected from hydrogen or a substituent group consisting of S1 to S192, and more preferably selected from hydrogen or a substituent group illustrated below.
  • Ar 3 to Ar 8 are the same or the same as each other, It is preferably selected from the group consisting of C 1 to C 40 alkyl groups, substituted or unsubstituted C 6 to C 60 aryl groups, and particularly preferably methyl or phenyl.
  • R 1 to R 12 are the same as or the same as each other, and are each independently selected from hydrogen or a substituent group consisting of S1 to S192, and more preferably selected from hydrogen or a substituent group illustrated below.
  • unsubstituted alkyl is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso -Amyl, hexyl and the like.
  • Unsubstituted alkenyl is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon double bonds, examples of which include vinyl, allyl (allyl), isopropenyl, 2-butenyl, and the like, but are not limited thereto.
  • Unsubstituted alkynyl is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon of 2 to 40 carbon atoms, having one or more carbon-carbon triple bonds, examples being ethynyl , 2-propynyl, and the like, but is not limited thereto.
  • Unsubstituted aryl means a monovalent substituent derived from an aromatic hydrocarbon of 6 to 60 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached in a simple or condensed form with one another. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Unsubstituted heteroaryl 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. It is understood that two or more rings may be attached in a simple or condensed form with each other, and further include condensed forms with aryl groups.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Unsubstituted aryloxy is a monovalent substituent represented by RO-, wherein R is an aryl having 5 to 60 carbon atoms.
  • R is an aryl having 5 to 60 carbon atoms.
  • aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Unsubstituted alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Unsubstituted arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Unsubstituted cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Unsubstituted heterocycloalkyl 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 or S Is substituted with a hetero atom such as Non-limiting examples thereof include 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 means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combined form thereof.
  • 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 includes an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode, and at least one of the at least one organic material layer.
  • a compound represented by Formula 1 preferably includes any one or more of the compound represented by Formula 3 to the compound represented by Formula 6.
  • the compounds represented by Formula 3 to Formula 6 may be used alone or in combination of two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, preferably a hole injection / transport layer, a light emitting layer or an electron transport layer, more preferably It 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 a light emitting layer material of the organic electroluminescent device, preferably a blue, green or red phosphorescent host, the binding force between holes and electrons in the light emitting layer is increased, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • the compound represented by Chemical Formula 1 may be included in the organic light emitting device as a blue, 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 described above 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 the present invention may be used as a phosphorescent host 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 known in the art, except that the at least one organic material layer (eg, the light emitting layer, the hole transport layer and / or the electron transport layer) is formed to include the compound represented by Formula 1 above. It can be prepared by forming other organic material layers and electrodes using materials and methods that are present.
  • the at least one organic material layer eg, the light emitting layer, the hole transport layer and / or the electron transport layer
  • 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 examples of anode materials that can be used include metals such as vanadium, chromium, copper, zinc, 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, 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-
  • Non-limiting examples of negative electrode materials 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- (biphenyl-4-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole instead of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole ( 3.72 g, 8.80 mmol) was subjected to the same process as in ⁇ Step 2> of Preparation Example 1, except that 6- (biphenyl-4-yl) -4- (2-nitrophenyl) -2,6 -dihydro-1H-benzo [def] carbazole was obtained.
  • 6- (biphenyl-3-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole instead of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole ( 3.73 g, 8.8 mmol) was subjected to the same process as in ⁇ Step 2> of Preparation Example 1, except that 6- (biphenyl-3-yl) -4- (2-nitrophenyl) -2,6 -dihydro-1H-benzo [def] carbazole was obtained.
  • IC-7-1 (4.74 g, 12.40 mmol), 1-bromobenzene (2.14 g, 37.18 mmol), Cu powder (0.15 g, 2.48 mmol), K 2 CO 3 (3.42 g, 24.79 mmol), Na under a stream of nitrogen. 2 SO 4 (3.53 g, 24.79 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 h.
  • tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) -carboxylate (2.06 g, 5.40 mmol) was dissolved in 50 ml of THF, followed by Potassium tert- at 0 ° C. butoxide (1.81 g, 16.13 mmol) was added and stirred for 10 minutes. Iodomethane (2.29 g, 16.13 mmol) was added thereto, followed by stirring at room temperature for 12 hours.
  • IC-1 (1.07 g, 3.00 mmol), 2-bromo-6-phenylpyridine (0.84 g, 3.60 mmol), Cu powder (0.027 g, 0.40 mmol), K 2 CO, which was a compound prepared in Preparation Example 1, under nitrogen stream. 3 (0.55 g, 0.40 mmol), Na 2 SO 4 (0.57 g, 4.00 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours.
  • Synthesis was performed in the same manner as in Synthesis Example 1, except that 4-bromodibenzo [b, d] thiophene was used instead of 2-bromo-6-phenylpyridine to obtain Inv-6 (1.22 g, yield 75%) as a target compound. .
  • Synthesis was performed in the same manner as in Synthesis Example 1, except that IC-7 and (4-bromophenyl) diphenylborane were used instead of IC-1 and 2-bromo-6-phenylpyridine, respectively. Yield 80%).
  • Synthesis was carried out in the same manner as in Synthesis Example 1, except that IC-7 and (4-bromophenyl) diphenylphosphine were used instead of IC-1 and 2-bromo-6-phenylpyridine, respectively. Yield 76%).
  • the compound Inv-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured as follows.
  • 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 and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • Example 1 except that the compound (Inv-2 ⁇ Inv-50) synthesized in Synthesis Examples 2 to 50 instead of the compound Inv-1 used as the light emitting host material when forming the light emitting layer in Example 1,
  • the organic EL device was fabricated as described above.
  • a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Inv-1 used as the light emitting host material when forming the emission layer.
  • the structure of CBP is as follows.
  • Example 1 Sample Host Drive voltage (V) Current efficiency (cd / A) Example 1 Inv-1 6.55 41.5 Example 2 Inv-2 6.49 41.0 Example 3 Inv-3 6.53 41.3 Example 4 Inv-4 6.55 40.9 Example 5 Inv-5 6.50 41.0 Example 6 Inv-6 6.52 41.2 Example 7 Inv-7 6.51 41.5 Example 8 Inv-8 6.44 40.8 Example 9 Inv-9 6.50 41.6 Example 10 Inv-10 6.45 41.3 Example 11 Inv-11 6.58 40.8 Example 12 Inv-12 6.60 41.0 Example 13 Inv-13 6.55 41.2 Example 14 Inv-14 6.50 41.7 Example 15 Inv-15 6.65 42.1 Example 16 Inv-16 6.60 41.5 Example 17 Inv-17 6.62 41.9 Example 18 Inv-18 6.50 41.7 Example 19 Inv-19 6.45 40.5 Example 20 Inv-20 6.52 41.5 Example 21 Inv-21 6.50 40.9 Example 22 Inv-22 6.60 41.5 Example 23 Inv-23 6.45 41.8 Example 24 Inv-24 6.52 40.8 Example 25 Inv-25 6.55 41.2 Example 26 Inv-26 6.58

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Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique comprenant celui-ci, et au moins une couche de matière organique, de préférence une couche d'émission, qui comprend ce nouveau composé, lequel permet d'améliorer considérablement l'efficacité d'émission lumineuse, la tension d'attaque et la durée de vie de l'élément.
PCT/KR2013/007955 2012-10-24 2013-09-04 Composé organique et élément électroluminescent organique comprenant celui-ci WO2014065501A1 (fr)

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KR102307359B1 (ko) * 2014-12-22 2021-10-05 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

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