WO2015125986A1 - Composé organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant un tel composé Download PDF

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WO2015125986A1
WO2015125986A1 PCT/KR2014/001393 KR2014001393W WO2015125986A1 WO 2015125986 A1 WO2015125986 A1 WO 2015125986A1 KR 2014001393 W KR2014001393 W KR 2014001393W WO 2015125986 A1 WO2015125986 A1 WO 2015125986A1
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group
formula
aryl
mmol
synthesis
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김성무
백영미
박호철
이창준
신진용
김태형
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주식회사 두산
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    • 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 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 Formula 1:
  • At least one of R 1 and R 2 , R 2 and R 3, or R 3 and R 4 combine with Formula 2 to form a condensed ring,
  • the dotted line represents a site where condensation occurs with the compound of Formula 1.
  • X 1 is N or CR 9 ,
  • X 2 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
  • Y 1 to Y 8 are the same as or different from each other, and each independently N or CR 10 , each R 10 may be the same or different,
  • R 1 to R 10 are the same or different and are each independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ alkynyl group of C 40 , C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, 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 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group and C 6 ⁇ C 40 It is selected from the group consisting of an arylsilyl group, these
  • 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 6 ⁇ C 40 Aryl group , nuclear atoms heteroaryl of 5 to 40 group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 cycloalkyl group , nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 group of the arylboronic, C 6 ⁇ C 40 aryl phosphine A pin group, a C 6 -C 40 arylphosphine oxide group, and a C 6 -C 40 arylsilyl group,
  • the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises a compound of Formula 1 It is an organic electroluminescent device characterized by.
  • 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, 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 Chemical Formula 1 is a blue, green or red phosphorescent host material.
  • the compound represented by Chemical Formula 1 of the present invention is excellent in thermal stability and phosphorescence property, it may be used as a material of the organic material layer of the organic EL device.
  • the compound represented by Chemical Formula 1 of 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, and further, performance And a full color display panel with greatly improved lifespan.
  • novel compounds according to the present invention are indolophenanthridine moiety or benzoimidazolophenanthridine moiety in the end of the indole (indole) moiety is fused to form a basic skeleton, such As a structure in which various substituents are bonded to the basic skeleton, it is represented by the formula (1).
  • the compound represented by Formula 1 has a wide bandgap due to the indolophenanthridine moiety or the indole moiety bound to the terminal of the benzoimidazolophenanthridine moiety.
  • the entire molecule has a bipolar (bipolar) properties, it is possible to increase the binding force between the hole and the electron. Therefore, the compound of Formula 1 may improve the phosphorescence property of the organic EL device and also improve the hole injection ability, transport ability, or luminous efficiency.
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the indole moiety, so that the glass transition temperature can be improved, and thus, the conventional CBP (4,4-dicarbazolybiphenyl) May have higher thermal stability.
  • the organic EL device including the compound of Formula 1 according to the present invention can greatly improve durability and lifespan characteristics.
  • the compound represented by the formula (1) of the present invention when adopted as a material of the hole injection / transport layer of the organic EL device as a phosphorescent host material of blue, green, and / or red, the efficiency and lifespan of the conventional CBP are excellent. It can exert an excellent effect. Therefore, the compound represented by Formula 1 of the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and the improvement of the life of the organic EL device can lead to the maximization of the performance in the full color organic light emitting panel.
  • Compound represented by the formula (1) of the present invention in combination with the formula (2) in which the condensed ring is formed may be more specifically represented by a compound represented by any one of the following formula (3).
  • Such compounds represented by the formulas (3) to (8) are preferred when considering the properties of the organic EL device.
  • X 1 , X 2, R 1 to R 8 and Y 1 to Y 8 are the same as defined in Chemical Formula 1, respectively.
  • X 1 is N or CR 9 and X 2 is selected from O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) .
  • X 1 is N or CR 9
  • X 2 is N (Ar 1 ), more preferably X 1 is N, and X 2 is N (Ar 1 ).
  • Y 1 to Y 8 are the same as or different from each other, and each independently N or CR 10, wherein each R 10 may be the same or different.
  • Y 1 to Y 8 are all CR 10, wherein each R 10 may be the same or different.
  • 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 6 ⁇ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ C 40 cycloalkyl, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ aryl boronic of C 40, a C 6 ⁇ C 40 Aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group and C 6 ⁇ C 40 It is selected from the group consisting of arylsilyls
  • Ar 1 to Ar 5 are the same or different from each other, each independently substituted or unsubstituted C 6 ⁇ C 40
  • R 1 to R 10 excluding R 1 and R 2 , R 2 and R 3 , and / or at least one of R 3 and R 4 are the same as each other. or different, and each independently represent hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ aryl of C 40 alkynyl group, C 6 ⁇ C 40 of group, nuclear atoms heteroaryl of 5 to 40 group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ cycloalkyl of C 40 alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C
  • R 1 to R 10 are each independently hydrogen, deuterium (D), substituted or unsubstituted C 6 ⁇ C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms and It is preferably selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 40 arylamine group.
  • an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes 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
  • Compound represented by the formula (1) of the present invention in combination with the formula (2) formed a condensed ring may be more preferably embodied as a compound represented by any one of the following formulas (9) to (20). Such compounds represented by the formulas (9) to (20) are more preferable in consideration of the characteristics of the organic EL device.
  • R 1 to R 8 and Ar 1 are as defined in Formula 1, respectively.
  • Ar 1 is 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 hetero Aryl group, C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom of 3 to 40 hetero Cycloalkyl 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, C 6 ⁇ C 40 aryl It is selected from the group consisting of a phosphine oxide group and a C 6 -C 40 arylsilyl group.
  • Ar 1 is preferably a substituted or unsubstituted C 6 ⁇ C 40 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms.
  • R 1 and R 2, R 2 and R 3, and / or R 3 and R 4 of R 1 to R 8 except for at least one or different, and each independently represent hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ aryl of C 40 alkynyl group, C 6 ⁇ C 40 of group, nuclear atoms heteroaryl of 5 to 40 group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, a C 3 ⁇ cycloalkyl of C 40 alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C
  • R 1 to R 8 are each independently hydrogen, deuterium (D), substituted or unsubstituted C 6 ⁇ C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, And it is preferably selected from the group consisting of a substituted or unsubstituted C 6 ⁇ C 40 arylamine group.
  • an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes 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
  • R 1 to R 10 and Ar 1 to Ar 5 are each independently selected from hydrogen or a substituent group represented by S1 to S204, but are not limited thereto.
  • R 1 to R 10 and Ar 1 to Ar 5 may be each independently selected from hydrogen or the following substituent groups.
  • alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, and iso-amyl. And hexyl.
  • alkenyl is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds. Examples thereof include vinyl and allyl. (allyl), isopropenyl, 2-butenyl, and the like.
  • 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. Examples thereof include ethynyl, 2-propynyl etc. are mentioned.
  • Aryl in the present invention 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 pendant or condensed with each other may also be included. Examples of such aryls include 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, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furany
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • R'O- monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • alkyloxy include 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 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 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 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), preferably a compound represented by the formula (3) to (8).
  • the compound of Formula 1 may be used alone, or two or more may be mixed.
  • 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 containing the compound of Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
  • the 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 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 represented by Formula 1 of the present invention may be used as a phosphorescent host material of the light emitting layer.
  • the 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 may be formed using other 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 can be produced by forming an organic material layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • 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.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • 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-chlorophenanthridine (18.8 g, 88.0 mmol), 2,5-dibromoaniline (24.3 g, 96.7 mmol), and 1000 ml of diglyme were added under nitrogen stream and stirred at 160 ° C. for 3 hours. After completion of the reaction, filtered, and recrystallized with EA and Hexane to obtain the target compound N- (2,5-dibromophenyl) phenanthridin-6-amine (29.4 g, 68.6 mmol, yield 78%).
  • N- (2,5-dibromophenyl) phenanthridin-6-amine (37.2 g, 87.0 mmol), triphenylphosphine (4.5 g, 17 mmol), palladium acetate (1.2 g, 5 mmol), pstassium carbonate (36.0 g 260) under nitrogen stream mmol) was added to 1000 ml of 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 organic layer filtered to obtain the target compound IPTN-Br (19.0 g, 54.8 mmol, 63% yield) by column chromatography.
  • IPTN-Br 30.6 g, 88.0 mmol
  • 4-bromo-1H-indole was carried out the same procedure as in ⁇ Step 1> of Preparation Example 1
  • IPTN1 (24.3 g, 62.5 mmol, yield 71% )
  • IPT-1 (3.56 g, 10.00 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.00 mmol), Cu powder (0.06 g) under nitrogen stream , 1.00 mmol), K 2 CO 3 (2.76 g, 20.00 mmol), Na 2 SO 4 (2.84 g, 20.00 mmol) and nitrobenzene (50 ml) were mixed and stirred at 200 ° C. for 12 hours.
  • 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 was used instead of Compound C 1 as a light emitting host material when forming the emission layer.
  • Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A)
  • Example 1 C 1 6.74 515 40.0
  • Example 2 C 2 6.46 518 41.8
  • Example 3 C 17 6.71 517 44.2
  • Example 4 C 19 6.79 515 41.7
  • Example 5 25 6.55 518 41.5
  • Example 6 C 27 6.69 515 42.7
  • Example 7 C 57 6.69 518 43.0
  • Example 8 C 58 6.70 517 43.3
  • Example 9 C 73 6.34 515 44.1
  • Example 10 C 75 6.70 518 41.4
  • Example 11 C 81 6.66 517 42.2
  • Example 12 C 83 6.65 518 43.1
  • Example 13 C 113 6.65 515 41.1
  • Example 14 C 114 6.71 518 42.0
  • Example 15 C 129 6.72 515 42.5
  • Example 16 131 6.72 518 41.3
  • Example 18 C C 139 6.73 517 41.6
  • the green organic EL device (Examples 1 to 61) using the compounds (C 1 to C 527) according to the present invention as a light emitting layer is a green organic EL device (Comparative Example 1) using a conventional CBP. Compared with, it can be seen that the better performance in terms of efficiency and driving voltage.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / C 129, C 493, C 496, C 498 + 10% (piq) 2 Ir (acac) (300nm) /
  • An organic electroluminescent device was manufactured by laminating in the order of BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
  • a red organic electroluminescent device was manufactured in the same manner as in Example 62, except that CBP was used instead of Compound C 129 as a light emitting host material when forming the emission layer.
  • red organic electroluminescent devices (Examples 62 to 65) using the compounds (C 129, C 493, C 496 and C 498) according to the present invention as the light emitting layer, the conventional CBP material of the light emitting layer Compared with the red organic electroluminescent element (Comparative Example 2) used, it can be seen that it shows excellent performance in terms of efficiency and driving voltage.

Abstract

La présente invention concerne un nouveau composé organique et un dispositif électroluminescent organique le comprenant, et permet d'obtenir un dispositif électroluminescent organique présentant des caractéristiques améliorées, comme l'efficacité lumineuse, la tension d'attaque, et la durée de vie, par introduction d'une couche d'émission de lumière, qui utilise un composé à base d'indolophénanthridine, en tant que substance hôte, dans le dispositif électroluminescent organique.
PCT/KR2014/001393 2014-02-20 2014-02-20 Composé organique et dispositif électroluminescent organique comprenant un tel composé WO2015125986A1 (fr)

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CN114380730B (zh) * 2021-12-16 2023-12-05 广西大学 硝基芳烃脱硝偶联合成n-芳基吡咯和n-芳基吲哚的方法
CN114478599A (zh) * 2022-02-16 2022-05-13 南京工业大学 一种含硼有机荧光分子及其制备方法和应用
CN114478599B (zh) * 2022-02-16 2023-10-13 南京工业大学 一种含硼有机荧光分子及其制备方法和应用

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