WO2015133804A1 - 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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WO2015133804A1
WO2015133804A1 PCT/KR2015/002066 KR2015002066W WO2015133804A1 WO 2015133804 A1 WO2015133804 A1 WO 2015133804A1 KR 2015002066 W KR2015002066 W KR 2015002066W WO 2015133804 A1 WO2015133804 A1 WO 2015133804A1
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group
aryl
formula
alkyl
boron
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백영미
김성무
이창준
신진용
이은정
박호철
김태형
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주식회사 두산
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom

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 at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • the material included in 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 according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color.
  • a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
  • a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
  • an object of the present invention is to provide an organic compound having a high glass transition temperature, excellent thermal stability, and improving the bonding force between holes and electrons.
  • Another object of the present invention is to provide an organic electroluminescent device including the organic compound and improved driving voltage and luminous efficiency.
  • the present invention provides a compound represented by the following formula (1).
  • X 1 is selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
  • Y 1 to Y 13 are each independently N or C (R 1 ),
  • Ar 1 to Ar 5 are each independently a C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyl silyl group, C 6 ⁇ C 60 aryl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 An arylphosphine oxide group and a C 6 ⁇ C 60 arylamine group, or combine with an adjacent group to form a condensed ring,
  • R 1 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 3 -C 40 cycloalkyl group, nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40 of the, aryloxy of C 6 ⁇ C 60 , C 1 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphine group , C 6
  • the group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl amine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C Alkynyl group of 2 to C 40 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group of, C
  • the present invention is an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises a compound represented by the formula (1)
  • An organic electroluminescent device is provided.
  • the organic compound of the present invention is dibenzoazine (5H-dibenzo [b, f] azepine), dibenzo oxepine (dibenzo [b, f] oxepine), dibenzo thiepine (dibenzo [b, f] thiepine)
  • the indole moiety is condensed to dibenzosilepine (5H-dibenzo [b, f] silepine) or dibenzocycloheptene (5H-dibenzo [a, d] cycloheptene) to form a basic skeleton. It is represented by Formula (1).
  • the host included in the phosphorescent layer should have a triplet energy gap higher than that of the dopant. That is, in order to effectively provide phosphorescence from the dopant, the energy of the lowest excited state of the host must be higher than the energy of the lowest emission state of the dopant.
  • the compound represented by Formula 1 of the present invention has a specific substituent introduced in the condensed indole derivative having a wide singlet energy level and a high triplet energy level, and thus may exhibit a higher energy level than the dopant when applied as a host of the emission layer. have.
  • the compound represented by Chemical Formula 1 of the present invention having a triplet energy of 2.3 eV or more prevents the excitons generated in the light emitting layer from diffusing to the adjacent electron transport layer or the hole transport layer, thereby increasing the number of excitons that contribute to light emission.
  • the luminous efficiency can be improved.
  • the compound represented by Formula 1 of the present invention may have a wide bandgap and a high carrier transport property by adjusting HOMO and LUMO energy levels according to the substituent introduced.
  • EWG electron withdrawal
  • EDG electron donor
  • the entire molecule may have a bipolar characteristic to increase the binding force between the hole and the electron.
  • the compound represented by Chemical Formula 1 of the present invention has various substituents, particularly aryl groups and / or heteroaryl groups, introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, thereby improving the conventional organic material layer material (for example, it may have higher thermal stability than CBP).
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer.
  • the compound represented by Chemical Formula 1 of the present invention may be formed into an organic material layer material of an organic EL device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / injection layer When applied as a material, light emitting auxiliary layer material, or lifespan improving layer material, it is possible to provide an organic EL device having improved performance and lifespan. As such, the organic EL device having improved performance and lifespan may maximize the performance of the full color organic light emitting panel.
  • X 1 is selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), Among them, it is preferred that N (Ar 1).
  • Ar 1 to Ar 5 are 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, 3 to 3 nuclear atoms 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C 1 to C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C It is selected from the group consisting of 60 aryl phosphine oxide group and C 6 ⁇ C 60 arylamine group, Among them, C 1 ⁇ C 40 Alkyl group, C 6 ⁇ C 60 Aryl group or nuclear hetero atoms of 5
  • Ar 1 is a C 6 ⁇ C 60 aryl group or a heteroaryl group of 5 to 60 nuclear atoms
  • Ar 2 to Ar 5 are each independently a C 1 ⁇ C 40 alkyl group (methyl group) or C 6 ⁇ that the aryl group (phenyl group), a C 60 are preferred.
  • Y 1 to Y 13 are each independently N or C (R 1 ), and all of them are preferably C (R 1 ) or one containing N. At this time, N contained one is preferably Y 5 .
  • R 1 is hydrogen, C 6 ⁇ C 60 aryl group, nuclear atoms, 5 to 60 heteroaryl group, and a C 6 ⁇ with an aryl amine of the C 60 It is preferably selected from the group consisting of.
  • at least one of two or more C (R 1 ) is preferably a substituent represented by Formula 1 below.
  • X 2 is selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), among which O, S or N (Ar 1 ) It is preferable that it is, more preferably N (Ar 1 ) (Ar 1 to Ar 5 is the same as defined in Formula 1).
  • L 1 is are selected from the group consisting of single bond, heteroarylene, C 6 ⁇ C 60 arylene group and a nuclear atoms of 5 to 60, and from preferably a single bond, phenylene or biphenylene.
  • the arylene group, heteroarylene group of L 1 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkyl of R 2 to R 9 Silyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ 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 to C 40 alkyloxy group, C 6 to C 60
  • Y 11 , Y 11 and Y 12, and one of Y 12 and Y 13 may all be C (R 1 ), and may combine with each other to form a condensed ring represented by the following Chemical Formula 3.
  • Dotted line is a part which is bonded to the formula (1),
  • X 3 is selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), among which O, S or N (Ar 1 ) It is preferable that it is, more preferably N (Ar 1 ) (Ar 1 to Ar 5 are the same as defined in Chemical Formula 1).
  • Y 14 to Y 17 are each independently N or C (R 1 ), and when two or more are C (R 1 ), C (R 1 ) is the same as or different from each other (R 1 is the same as defined in Formula 1 above) box).
  • X 1 , X 3 and Y 1 to Y 17 are the same as defined in the formula (1) and (3).
  • Ar 1 is C 6 ⁇ C 60 Aryl group or nuclear atom 5 It is preferable that it is a heteroaryl group of 60, and it is more preferable that it is a substituent represented by following formula (16). That is, at least one of X 1 to X 3 is N (Ar 1 ), wherein Ar 1 is a substituent represented by the following formula (16).
  • L 2 is preferably a single bond, C 6 ⁇ C 18 arylene group, and there is a selected from the group nuclear atoms of 5 to 18 heteroarylene group consisting of a single bond from the phenyl group or a biphenylene group.
  • Z 1 to Z 5 are each independently N or C (R 11 ), wherein at least one of Z 1 to Z 5 is N.
  • a plurality of C (R 11 ) may be 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 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C 6 ⁇ aryloxy C 60 C 1 ⁇ C 40 alkyloxy group, the C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, C 6 ⁇ C 60 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group is selected from the pin, and the group consisting of C 6 ⁇ C 60 aryl group in the
  • the L-arylene group, heteroarylene group, an alkyl group of R 11 2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkyl Silyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group.
  • Substituents represented by Formula 16 may be embodied by substituents represented by the following A-1 to A-15.
  • L 2 and R 11 are the same as defined in Chemical Formula 16, wherein a plurality of R 11 are the same as or different from each other.
  • R 21 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 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C 6 ⁇ aryloxy C 60 C 1 ⁇ C 40 alkyloxy group, the C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, C 6 ⁇ C 60 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the group consisting of C 60 or aryl silyl
  • n is an integer of 1-4.
  • An aryl phosphine group, an aryl phosphine oxide group, and an aryl silyl group are each independently deuterium, halogen, cyano group, and nitro group.
  • Ar 1 to Ar 5 and R 1 may be independently selected from the group consisting of the following substituents (S1 to S204), but is not limited thereto.
  • the compound represented by Formula 1 of the present invention may be represented by the following compounds in more detail, but is not limited thereto.
  • alkyl means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms.
  • Non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • Alkenyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl and the like.
  • Alkynyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond.
  • Non-limiting examples thereof include ethynyl, 2-propynyl and the like.
  • Cycloalkyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon).
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to Three carbons are substituted with a hetero atom such as N, O or S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • aryl means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
  • the two or more rings may be attached in a simple or condensed form with each other.
  • Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.
  • Heteroaryl in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and has at least one carbon, preferably 1 to 3 carbon atoms in the ring. Carbon is substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se).
  • the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group.
  • heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Alkyloxy in the present invention means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, may include a linear, branched or cyclic structure. have.
  • alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Aryloxy in the present invention means a monovalent functional group represented by R'O-, wherein R 'is an aryl having 6 to 60 carbon atoms.
  • R ' is an aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkylsilyl in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms
  • arylamine is substituted with aryl having 6 to 60 carbon atoms Means amine.
  • 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 present invention includes an anode, a cathode and at least one organic layer interposed between the anode and the cathode, and at least one of the at least one organic layer includes the compound represented by Formula 1 It provides an organic electroluminescent device.
  • the compounds may be used alone or in combination of two or more.
  • the at least one organic material layer may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • the organic material layer including the compound represented by Chemical 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, wherein the host may include a compound represented by the formula (1).
  • the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic EL device, preferably a blue, green or red phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased, so that the efficiency of the organic EL device is improved. Efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • 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 layer, an electron transport layer, and a cathode are sequentially stacked. An electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted between the electrode and the organic material layer interface.
  • the organic electroluminescent device of the present invention is formed of another organic layer and electrode by a material and a method known in the art, except that at least one layer (eg, a light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming.
  • 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.
  • a silicon wafer quartz, glass plate, metal plate, plastic film, or the like may be used.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy 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 and the like can be used.
  • 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), poly
  • the negative electrode material may be magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or a metal such as lead or an alloy thereof, and a multilayer such as LiF / Al or LiO 2 / Al. Structural materials and the like can be used.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.
  • IC-2-1 (7.29 g, 23.0 mmol), iodobenzene (14.1 g, 69.0 mmol), Cu powder (0.15 g, 2.30 mmol), K 2 CO 3 (6.30 g, 46.0 mmol), Na 2 SO under nitrogen stream. 4 (6.50 g, 46.0 mmol) and nitrobenzene (150 ml) were mixed and stirred at 200 ° 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 . The solvent was removed from the organic layer to which water was removed, and then purified by column chromatography to obtain IC-2-2 (6.69 g, yield 74%).
  • IC-2-2 (11.8 g, 30.0 mmol), 9H-carbazol-3-ylboronic acid (6.97 g, 33.0 mmol), X-phos (1.43 g, 3.00 mmol), Cs 2 CO 3 (19.5 g , 60.0 mmol) and Tol / EtOH / H 2 O (120 ml / 60 ml / 60 ml) were mixed, Pd (OAc) 2 (0.34 g, 5 mol%) was added thereto, and the mixture was stirred at 110 ° C. for 12 hours. . After completion of the reaction, the mixture was extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain IC-2 (11.2 g, yield 71%).
  • IC-2-2 (11.8 g, 30.0 mmol), 2-nitrophenylboronic acid (5.51 g, 33.0 mmol), X-phos (1.43 g, 3.00 mmol), Cs 2 CO 3 (19.5 g, 60.0 mmol) And Tol / EtOH / H 2 O (120 ml / 60 ml / 60 ml) were mixed, Pd (OAc) 2 (0.34 g, 5 mol%) was added thereto, and the mixture was stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the organic layer and purified by column chromatography to obtain IC-3-1 (11.2 g, yield 78%).
  • IC-3-1 (9.59 g, 20.0 mmol), triphenylphosphine (15.7 g, 60.00 mmol) and 1,2-dichlorobenzene (100 ml) were mixed and stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. To the obtained organic layer, water was removed with MgSO 4 and purified by column chromatography to obtain IC-3 (3.94 g, yield 44%) and IC-4 (3.92 g, yield 44%).
  • IC-1 (2.82 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd 2 (dba) 3 (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 to obtain the target compound C-65 (4.37 g, yield 85%) using column chromatography.
  • N-diphenylaniline (3.24 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine C-116 (3.68 g, yield 70%) was obtained as the target compound.
  • a target compound C-308 (6.11 g, 81% yield) was obtained in the same manner as Synthesis Example 12, except that IC-3 (4.48 g, 10.00 mmol) was used instead of IC-1.
  • a target compound C-309 (5.73 g, 76% yield) was obtained in the same manner as in Synthesis Example 11, except that IC-3 (4.48 g, 10.00 mmol) was used instead of IC-1.
  • a target compound C-310 (6.57 g, 87% yield) was obtained in the same manner as in Synthesis Example 13, except that IC-3 (4.48 g, 10.00 mmol) was used instead of IC-1.
  • a target compound C-323 (6.18 g, 82% yield) was obtained in the same manner as in Synthesis Example 11, except that IC-4 (4.48 g, 10.00 mmol) was used instead of IC-1.
  • IC-2 (5.24 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.00 mmol), Pd 2 (dba) 3 (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 to obtain a target compound C-332 (6.27 g, 83% yield) by column chromatography.
  • the device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a 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 to form an emission layer.
  • Example 1 Sample Host compound Drive voltage (V) Light emitting peak (nm) Current efficiency (cd / A) Example 1 C-65 6.45 517 41.8 Example 2 C-4 6.55 515 43.1 Example 3 C-9 6.50 518 43.2 Example 4 C-12 6.45 518 41.5 Example 5 C-16 6.50 518 41.9 Example 6 C-19 6.45 517 41.7 Example 7 C-62 6.45 517 41.6 Example 8 C-63 6.50 518 40.3 Example 9 C-68 6.55 518 39.9 Example 10 C-69 6.60 517 41.3 Example 11 C-73 6.50 515 41.3 Example 12 C-74 6.50 516 43.1 Example 13 C-75 6.55 518 43.0 Example 14 C-165 6.50 517 41.4 Example 15 C-104 6.65 518 42.2 Example 16 C-109 6.60 517 42.0 Example 17 C-112 6.60 515 41.6 Example 18 C-116 6.50 518 41.5 Example 19 C-119 6.55 518 41.4 Example 20 C-162 6.50 518 41.9 Example 21 C-163 6.50 5
  • the device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a device was manufactured in the same manner as in Example 43, except that Alq 3 was used instead of Compound C-4 when forming the ETL.
  • NPB, ADN and Alq 3 used in Examples 43 to 49 and Comparative Example 2 are as follows.
  • the compound of the present invention has excellent thermal stability, electron and hole transport ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspects such as light emission performance, driving voltage, lifetime, and efficiency are greatly improved.

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  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé organique et un dispositif organique électroluminescent le comprenant. Le composé organique de la présente invention est utilisé pour une couche de matériau organique d'un dispositif électroluminescent organique, ce qui permet d'améliorer le rendement d'émission de lumière, la tension de commande, la durée de vie, etc du dispositif électroluminescent organique.
PCT/KR2015/002066 2014-03-04 2015-03-04 Composé organique et dispositif électroluminescent organique comprenant un tel composé WO2015133804A1 (fr)

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CN106910833B (zh) * 2015-12-22 2020-08-07 三星显示有限公司 有机发光装置
EP3185329A1 (fr) * 2015-12-22 2017-06-28 Samsung Display Co., Ltd. Dispositif électroluminescent organique
CN106910833A (zh) * 2015-12-22 2017-06-30 三星显示有限公司 有机发光装置
CN106981576A (zh) * 2015-12-22 2017-07-25 三星显示有限公司 有机发光装置
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EP3185328A1 (fr) * 2015-12-22 2017-06-28 Samsung Display Co., Ltd. Dispositif électroluminescent organique
CN111048677A (zh) * 2015-12-22 2020-04-21 三星显示有限公司 有机发光装置
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US11696496B2 (en) 2015-12-22 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
CN111048677B (zh) * 2015-12-22 2022-09-23 三星显示有限公司 有机发光装置
US11617290B2 (en) * 2015-12-22 2023-03-28 Samsung Display Co., Ltd. Organic light-emitting device
CN105884673A (zh) * 2016-06-03 2016-08-24 温州大学 一种吲哚衍生物的合成方法
CN105884673B (zh) * 2016-06-03 2018-05-11 温州大学 一种吲哚衍生物的合成方法
CN112300179A (zh) * 2019-07-30 2021-02-02 北京鼎材科技有限公司 一种化合物、包含其的有机电子发光器件及其应用

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