WO2015122711A1 - 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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WO2015122711A1
WO2015122711A1 PCT/KR2015/001454 KR2015001454W WO2015122711A1 WO 2015122711 A1 WO2015122711 A1 WO 2015122711A1 KR 2015001454 W KR2015001454 W KR 2015001454W WO 2015122711 A1 WO2015122711 A1 WO 2015122711A1
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group
substituted
unsubstituted
aryl
formula
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백영미
김성무
이창준
신진용
이은정
박호철
김태형
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주식회사 두산
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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.
  • the existing materials have advantages in terms of light emission characteristics, but the thermal stability is low due to the low glass transition temperature, and thus the materials are not satisfactory in terms of lifespan of the organic EL device.
  • an object of the present invention is to provide a novel organic compound having a high glass transition temperature and excellent thermal stability.
  • Another object of the present invention is to provide an organic electroluminescent device comprising the organic compound.
  • the present invention provides a compound represented by the following formula (1) or (2).
  • X 1 and X 2 are the same as or different from each other, and each independently O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) Wherein at least one of X 1 and X 2 is N (Ar 1 );
  • L 1 is selected from the group consisting of a single bond, a substituted or unsubstituted C 6 ⁇ C 60 arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms,
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 Alkynyl group of -C 40 , substituted or unsubstituted C 6 -C 40 aryl group, substituted or unsubstituted heteroaryl group of 5 to 40 nuclear atoms, substituted or unsubstituted C 6 -C 40 aryl jade Periodic, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine 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 1 to C
  • R 1 to R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkene Nyl group, substituted or unsubstituted C 2 to C 40 alkynyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 40 aryloxy group, substituted or unsubstituted C 1 ⁇ C 40 Alkyloxy group, substituted or unsubstituted C 6 ⁇ C 40 arylamine group, substituted or unsubstituted C 3 ⁇ C 40 cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 3 to 40 nuclear atoms, substituted or unsubstitute
  • 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 and aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group , C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of, C 6 ⁇ C 40 arylamine group, C 3
  • a and c are each independently an integer of 0-4, b is an integer of 0-3, d is an integer of 0-6.
  • the present invention also includes 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 electroluminescent device is provided.
  • the organic material layer including the compound represented by Chemical Formula 1 may be a phosphorescent light emitting layer, a hole transport layer or an auxiliary light emitting layer.
  • the compound represented by Chemical Formula 1 of the present invention may be used as a material of the organic material layer of the organic EL device because of its excellent thermal stability and phosphorescence properties.
  • 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 furthermore, Full color display panels with improved lifetime can also be manufactured.
  • novel compounds according to the present invention are prepared in the following moieties in dibenzo moieties (dibenzothiophenes, dibenzofurans, dibenzosilols, dibenzoselenophenes, carbazoles or fluorenes) in combination with 5-membered aromatic rings or 5-membered heteroaromatic rings.
  • dibenzo moieties dibenzothiophenes, dibenzofurans, dibenzosilols, dibenzoselenophenes, carbazoles or fluorenes
  • a structure in which a tee is bonded is used as a basic skeleton, and is represented by Formula 1 or Formula 2.
  • Carbazole or benzoacridine moiety (7H-benzo [kl] acridine moiety) has excellent hole transporting ability and has a certain level of hole mobility, so that the compound represented by Chemical Formula 1 or 2 is formed in an organic electric field.
  • an organic material layer specifically, a hole transport layer
  • the organic EL device When applied to the organic material layer of the bonding force between the hole and the electron in the organic material layer (specifically, the light emitting layer) can be increased. Therefore, the light emitting characteristics of the organic EL device can be improved, and at the same time, the carrier injection ability, the transport ability, or the light emission efficiency can be improved.
  • the compound represented by Formula 1 or 2 can limit the excitons formed in the organic material layer to move to another organic material layer (specifically, the excitons formed in the light emitting layer to move to the hole transport layer), the life of the organic EL device And efficiency can also be improved.
  • the compound represented by Chemical Formula 1 or 2 has various substituents, especially aryl groups and / or heteroaryl groups, so that the molecular weight of the compound is significantly increased, thereby improving the glass transition temperature, and thus the conventional organic material layer material (eg For example, it may have higher thermal stability than CBP).
  • the compound represented by the formula (1) or (2) is effective in suppressing the crystallization of the organic material layer.
  • the performance and lifespan characteristics of the organic EL device may be greatly improved. have.
  • the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • L 1 may be a linker of a conventional divalent group known in the art.
  • it may be selected from the group consisting of a single bond, a substituted or unsubstituted C 6 ⁇ C 40 arylene group and a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms.
  • Non-limiting examples of the arylene group and hetero arylene group are phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, And a furinylene group, a quinolinyl group, a pyrroylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group, and the like.
  • L 1 is preferably a single bond, a phenylene group, or a biphenylene group.
  • X 1 and X 2 are the same as or different from each other, and each independently O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) And Si (Ar 4 ) (Ar 5 ), wherein at least one of X 1 and X 2 is N (Ar 1 ). Specifically, it is preferable when X 1 is N (Ar 1 ).
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, substituted or unsubstituted C 6 to C 40 aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 40 aryl Oxy group, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted A substituted heterocycloalkyl group having 3 to 40 ring atoms, a substituted or unsubstituted C 1 to C 40 al
  • Ar 1 to Ar 5 are each independently a substituted or unsubstituted C 1 ⁇ C 40 alkyl group, a substituted or unsubstituted C 6 ⁇ C 40 aryl group and a substituted or unsubstituted nuclear atom 5 to 40 It is preferably selected from the group consisting of a heteroaryl group, more preferably a methyl group or a phenyl group.
  • Ar 1 to Ar 5 and R 1 to R 4 may be selected from the group consisting of hydrogen or the following substituents S1 to S206. However, it is not limited to this.
  • At least one of Ar 1 to Ar 5 is preferably represented by the following general formula (3), and more preferably Ar 1 is represented by the general formula (3).
  • '*' means a site that is combined with nitrogen (N).
  • L may be a conventional divalent group linking group known in the art, for example, a single bond, a substituted or unsubstituted C 6 -C 18 arylene group and a substituted or unsubstituted nuclear atom 5 to 18 It may be selected from the group consisting of a hetero arylene group.
  • L More specific examples of L include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, a furinylene group, and a quinolyne group A niylene group, a pyrrolyylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group, and the like.
  • L is preferably a single bond, a phenylene group or a biphenylene group.
  • Y 1 to Y 5 are each independently N or C (R 11 ), wherein at least one of Y 1 to Y 5 is preferably N.
  • R 11 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 An alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 40 aryloxy group, substituted or Unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl groups, substituted or unsubstituted C 1 to C 40 alkylsilyl groups, substitute
  • the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group of R 11 is cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group,
  • the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 heteroaryl group, the aryl group, the number of nuclear atoms of 5 to 40 C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 groups of the cycloalkyl
  • Substituents represented by the general formula (3) may be more embodied in any one of a substituent group consisting of a structure (substituent) represented by A-1 to A-15.
  • R 12 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C 1 to C 40 alkyl group, substituted or unsubstituted C 2 to C 40 alkenyl group, substituted or unsubstituted C 2 to C 40 An alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, a substituted or unsubstituted C 6 to C 40 aryloxy group, substituted or Unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 to C 40 arylamine group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl groups, substituted or unsubstituted C 1 to C 40 alkylsilyl groups, substitute
  • the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 heteroaryl group, the aryl group, the number of nuclear atoms of 5 to 40 C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 groups of the cycloalkyl
  • Formula 3 may be selected from a substituent group consisting of the following structures (substituents).
  • the compound represented by Formula 1 or 2 of the present invention may be more specific with any one of the compounds represented by the following formula 4 to formula 6.
  • X 1 and X 2 , R 1 to R 4, a to d are the same as defined in Chemical Formula 1.
  • X 1 and X 2 are the same or different from each other, and each independently O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4) ) (Ar 5 ), wherein at least one of X 1 and X 2 is N (Ar 1 ),
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 40 alkyl group, a C 6 to C 40 aryl group, and a substituted or unsubstituted nuclear atom 5 to 40 Is selected from the group consisting of heteroaryl groups,
  • R 1 to R 4 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted It is selected from the group consisting of a heteroaryl group having 5 to 40 nuclear atoms, and a substituted or unsubstituted C 6 ⁇ C 40 arylamine group.
  • Compound represented by the formula (1) of the present invention described above may be more specific to the compounds exemplified below, for example, compounds represented by C-1 to C-300.
  • the compound represented by Formula 1 of the present invention is not limited to the following compounds.
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • alkenyl 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, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples thereof include ethynyl, 2-propynyl and the like, but are not limited thereto.
  • 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 aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are simply attached or condensed with each other may also be included, and is also construed to include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
  • R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 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 represented by Formula 1 or Formula 2 of the present invention may be synthesized according to a general synthesis method. Such compounds of the present invention can be synthesized in various ways with reference to the following synthesis examples.
  • organic electroluminescent device comprising the compound represented by the formula (1) or 2 according to the present invention described above.
  • the organic electroluminescent device 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.
  • a compound represented by the formula (1) or (2) includes a compound represented by the formula (1) or (2).
  • 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 light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer includes a compound represented by Formula 1 or 2 can do.
  • the organic material layer including the compound of Formula 1 or 2 is preferably a light emitting layer, a hole transport layer or a light emitting auxiliary 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 or 2 as the host material.
  • the compound of Formula 1 or 2 when included as the light emitting layer material of the organic electroluminescent device, preferably blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light emitting layer is increased, and thus, the organic electroluminescence
  • the efficiency (light emitting efficiency and power efficiency), lifetime, luminance and driving voltage of the device can be improved.
  • the compound represented by Formula 1 or 2 of the present invention when used as the light emitting auxiliary layer, it may be located between the hole transport layer and the light emitting layer. In this case, the compound may be a phosphorescent auxiliary layer. In this case, the luminous efficiency, luminance, power efficiency, thermal stability and lifespan of the device may be improved due to the compound.
  • 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.
  • the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a hole transport layer, light emitting auxiliary layer, light emitting layer It may include a compound represented by the formula (1).
  • the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer.
  • an electron injection layer may be further stacked on the electron transport layer.
  • the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.
  • the organic electroluminescent device of the present invention forms an organic material layer and an electrode by a material and a method known in the art, except that at least one layer (preferably a light emitting layer) of the organic material layer includes the compound represented by Chemical Formula 1. It can manufacture.
  • 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 the manufacture of the organic EL device of the present invention is not particularly limited, but 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, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
  • a target compound C-9 (5.39 g, 71% yield) was obtained in the same manner as in Synthesis Example 1, except that 2- (4-bromophenyl) triphenylene (3.82 g, 10.00 mmol) was used instead of bromobenzene. .
  • a target compound was carried out in the same manner as in Synthesis Example 1, except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.43 g, 10.00 mmol) was used instead of bromobenzene.
  • C-75 (5.35 g, yield 70%) was obtained.
  • a target compound C-109 (4.72 g, 69% yield) was obtained in the same manner as in Synthesis Example 3, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.
  • the target compound C-165 (4.11 g, 67% yield) was obtained by the same method as the synthesis example 11 above.
  • a target compound C-168 (4.89 g, 71% yield) was obtained in the same manner as in Synthesis Example 12, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.
  • a target compound C-169 (4.75 g, 69% yield) was obtained in the same manner as Synthesis Example 13, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.
  • a target compound C-173 (5.02 g, 73% yield) was obtained by the same method as the synthesis example 14 except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.
  • a target compound C-175 (4.96 g, 72% yield) was obtained in the same manner as Synthesis Example 16, except that IC1-2 (3.83 g, 10.00 mmol) was used instead of IC1-1.
  • a target compound C-263 (4.08 g, 65% yield) was obtained in the same manner as in Synthesis Example 10, except that IC1-3 (3.99 g, 10.00 mmol) was used instead of IC1-1.
  • 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 Driving voltage (V) EL peak (mm) Current efficiency (cd / A) Example 1 C-1 6.70 517 41.2 Example 2 C-7 6.66 518 40.7 Example 3 C-9 6.55 517 39.9 Example 4 C-11 6.70 516 40.1 Example 5 C-12 6.60 518 39.6 Example 6 C-16 6.68 518 39.3 Example 7 C-19 6.65 517 40.7 Example 8 C-30 6.68 518 39.9 Example 9 C-62 6.65 517 41.1 Example 10 C-63 6.50 517 41.1 Example 11 C-65 6.55 518 41.4 Example 12 C-68 6.50 518 41.5 Example 13 C-69 6.60 516 41.9 Example 14 C-73 6.55 518 41.3 Example 15 C-74 6.45 517 42.1 Example 16 C-75 6.60 518 42.3 Example 17 C-101 6.71 518 39.1 Example 18 C-107 6.67 517 39.1 Example 19 C-109 6.58 516 38.9 Example 20 C-111 6.76 518 40.1 Example 21 C-112 6.72 517
  • the green organic EL device of Examples 1-48 using the compound according to the present invention as the light emitting layer of the green organic EL device was compared with the green organic EL device of Comparative Example 1 using the conventional CBP. It was found that the better performance in terms of efficiency and driving voltage.

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  • Spectroscopy & Molecular Physics (AREA)
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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le comprenant. Le composé selon la présente invention permet d'améliorer l'efficacité d'émission de lumière, la tension de commande, la durée de vie, etc. d'un dispositif organique électroluminescent, ledit composé étant utilisé dans une couche organique, de préférence une couche luminescente, du dispositif électroluminescent organique.
PCT/KR2015/001454 2014-02-14 2015-02-13 Composé organique et dispositif électroluminescent organique comprenant un tel composé WO2015122711A1 (fr)

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CN110724132A (zh) * 2019-10-29 2020-01-24 上海天马有机发光显示技术有限公司 一种化合物、显示面板、显示装置
CN111683942A (zh) * 2018-03-23 2020-09-18 Sk材料有限公司 化合物、有机发光器件及显示装置
CN111777586A (zh) * 2020-07-29 2020-10-16 西安瑞联新材料股份有限公司 一种10-氯苯并[kl]呫吨化合物的制备方法
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WO2022091691A1 (fr) * 2020-10-27 2022-05-05 出光興産株式会社 Composé, élément électroluminescent organique et dispositif électronique

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KR101984786B1 (ko) * 2015-04-15 2019-05-31 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102471570B1 (ko) * 2017-11-30 2022-11-28 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN111868048B (zh) 2018-04-19 2023-05-19 株式会社Lg化学 化合物和包含其的有机发光器件
CN114957188A (zh) * 2021-02-26 2022-08-30 阜阳欣奕华材料科技有限公司 化合物与有机电致发光器件以及中间体化合物
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