WO2014046392A1 - Composé organique et élément électroluminescent le comportant - Google Patents

Composé organique et élément électroluminescent le comportant Download PDF

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WO2014046392A1
WO2014046392A1 PCT/KR2013/007821 KR2013007821W WO2014046392A1 WO 2014046392 A1 WO2014046392 A1 WO 2014046392A1 KR 2013007821 W KR2013007821 W KR 2013007821W WO 2014046392 A1 WO2014046392 A1 WO 2014046392A1
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이용환
김태형
손효석
배형찬
박호철
이창준
신진용
백영미
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주식회사 두산
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic compound having excellent hole injection ability, hole transport ability and light emission ability, and the like as a material of the organic material layer
  • the present invention relates to an organic EL device having improved characteristics such as efficiency, driving voltage, and lifetime.
  • the material used as the organic material layer may be classified into a light emitting layer material, a hole injection layer material, a hole transport layer material, an electron transport layer material, an electron injection layer material and the like according to its function.
  • the material ('light emitting layer material') forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting material according to the light emitting color.
  • yellow and orange light emitting layer materials are also used as the light emitting layer material to realize a better natural color.
  • a host / dopant system may be used as the light emitting layer 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.
  • the development of phosphorescent materials can theoretically improve luminous efficiency up to four times that of fluorescence, attracting attention not only on phosphorescent dopants but also on phosphorescent host materials.
  • hole transport layer material As the hole transport layer material, the hole blocking layer material, and the electron transport layer material, NPB, BCP, Alq 3 and the like represented by the following formulas are widely known, and as the light emitting layer material, anthracene derivatives have been reported as fluorescent dopant / host materials.
  • phosphorescent materials having great advantages in terms of efficiency improvement include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which are blue, green, and red plated materials. It is used as a raw material. To date, CBP has shown excellent properties as a phosphorescent host material.
  • an object of the present invention is to provide a novel organic compound that can be used as a light emitting layer material and can improve the efficiency, life and stability of the device when used in the light emitting layer of the organic electroluminescent device.
  • an object of this invention is to provide the organic electroluminescent element containing the said novel organic compound.
  • the present invention provides a compound represented by the following formula (1):
  • Ring A is a 6-membered heterocycle containing CR 3 and N, a 6-membered ring substituted with R 3 , or a 6-membered heterocycle containing two N;
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein X At least one of 1 and X 2 is N (Ar 1 );
  • Y 1 to Y 4 are the same as or different from each other, and each independently N or CR 4, wherein, when there are a plurality of CR 4 , they are different from each other or the same;
  • a is 1 or 2;
  • L represents a substituted or unsubstituted C 6 to C 60 arylene group, a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, a substituted or unsubstituted aryl-triyl, or a substituted or Unsubstituted heteroaryl-triyl,
  • L is a substituted or unsubstituted C 6 to C 60 arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms,
  • L is substituted or unsubstituted aryl-triyl, or substituted or unsubstituted heteroaryl-triyl;
  • B is a substituted or unsubstituted carbazole group, or a substituent represented by the following formula (3), wherein when B is plural, they are different from each other or the same;
  • Ring C is a 6-membered heterocycle containing CR 7 and N, a 6-membered ring substituted with R 7 , or a 6-membered heterocycle containing two N;
  • X 3 and X 4 are each independently selected from the group consisting of O, S, Se, N (Ar 6 ), C (Ar 7 ) (Ar 8 ) and Si (Ar 9 ) (Ar 10 ),
  • Y 5 to Y 8 are the same as or different from each other, and each independently N or CR 8, wherein, when a plurality of CR 8 plurals, they are different from or the same;
  • R 5 to R 8 and Ar 6 to Ar 10 is a single bond, connected to L of Formula 2;
  • R 1 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C 1 -C 40 alkyl group, a 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 Substituted 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 ⁇ C 60 aryloxy group, substituted or unsubstituted C 3 to C 40 alkyl
  • Ar 1 to Ar 10 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 3 to C 40 A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C 6 -C 60 aryl group, a 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 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 40 alkylsilyl group, substituted or unsubstituted C 6 ⁇ C 60 arylsilyl group, substituted or unsubstituted C 1 ⁇ C 40 Al
  • One or more substituents respectively introduced to the arylborone group, the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl group, C 3 -C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear
  • the present invention is an organic EL device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic EL device which is characterized by including.
  • the organic material layer including the compound represented by Chemical Formula 1 is selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer, and is preferably a light emitting layer.
  • the compound represented by Chemical Formula 1 is included in the emission layer, it may be used as a host material and / or a dopant.
  • the compound represented by Formula 1 according to the present invention is excellent in heat resistance, hole injection ability, hole transporting ability, light emitting ability, etc.
  • the compound may be applied to an organic material layer, preferably a light emitting layer of an organic EL device.
  • the organic electroluminescent device includes the compound represented by Chemical Formula 1 as a hole injection layer material, a hole transport layer material, or a light emitting layer material (phosphorescent / fluorescent host, dopant) or the like, the light emitting performance, driving voltage, Since aspects such as lifespan, efficiency (light emitting efficiency, power efficiency) and the like can be greatly improved, they can be effectively applied to a full color display panel or the like.
  • novel organic compound according to the present invention is applied to an indoloindole-based basic skeleton formed by condensation of an indole-based moiety and an indole-based moiety, and a cover through a linking group (L).
  • a structure in which an indoloindole moiety in which a doze group or an indole moiety is condensed with an indole moiety is combined, is represented by Chemical Formula 1.
  • Compound represented by the formula (1) has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')] has a high glass transition temperature, and also excellent thermal stability, It has excellent hole injecting ability, hole transporting ability and light emitting ability. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
  • the conventional organic EL device material for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolybiphenyl
  • the compound represented by Formula 1 is an indoloindole-based moiety or carbazole group through the linking group (L) to an indoloindole-based basic skeleton formed by condensation of an indole-based moiety and an indole-based moiety By being combined, it has a wide bandgap (sky blue to red).
  • an indoloindole moiety or a carbazole group is bonded to an N position of an indole moiety in a basic skeleton condensed between an indole moiety and an indole moiety through a linking group (eg, arylene, heteroarylene, etc.).
  • the bandgap of the compound is widened and the triplet energy level is widened, thereby improving the phosphorescence property of the device and at the same time improving the electron and / or hole transport ability, the luminous efficiency, the driving voltage, and the life characteristics.
  • the electron transport ability etc. can also be improved according to the kind of substituent introduce
  • the compound of Formula 1 may optionally be used as a material of the electron transport layer by introducing an appropriate substituent.
  • the compound of Formula 1 may exhibit excellent properties as a light emitting layer material, especially a host material, compared to the conventional CBP due to the indoloindole-based skeleton.
  • the compound represented by Formula 1 has a variety of aryl groups and / or heteroaryl groups introduced into the indoloindole-based basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby resulting in higher than conventional CBP It can have a high thermal stability. Therefore, the device including the compound represented by the formula (1) of the present invention can greatly improve the durability and life characteristics.
  • the compound represented by Formula 1 has a small difference between the triplet energy level and the singlet energy level, so that the reverse energy transfer from the triplet to the singlet may occur.
  • thermally activated delayed fluorescence occurs, thereby improving external quantum efficiency of the device, and when the compound is used as a light emitting layer material, the light emission efficiency of the device may be increased.
  • the compound of the present invention When the compound of the present invention is adopted as a hole injection / transport layer of an organic EL device, a blue, green and / or red phosphorescent host material or a fluorescent dopant material, the compound can exhibit excellent efficiency and lifespan in comparison with the 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.
  • ring A is a 6-membered heterocycle containing CR 3 and N, a 6-membered cycle substituted with R 3 , or two It is a 6-membered heterocycle containing N, Preferably it is a 6-membered ring substituted with R ⁇ 3> .
  • X 1 and X 2 are each independently selected from O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein X At least one of 1 and X 2 is N (Ar 1 ).
  • Preferably both X 1 and X 2 are N (Ar 1 ), or X 1 and X 2 are each independently N (Ar 1 ) or S.
  • Y 1 to Y 4 are the same as or different from each other, and each independently N or CR 4 , and preferably Y 1 to Y 4 are all CR 4 . At this time, when there are a plurality of CR 4 , they are different from each other or the same.
  • R 1 to R 4 is a substituent represented by Chemical Formula 2.
  • a is 1 or 2.
  • L is a substituted or unsubstituted C 6 ⁇ C 60 arylene group, a substituted or unsubstituted heteroarylene group having 5 to 60 nuclear atoms, a substituted or unsubstituted aryl-triyl group (aryl-triyl group) Or a substituted or unsubstituted heteroaryl-triyl group, provided that when a is 1, L is a substituted or unsubstituted C 6 -C 60 arylene group, or a substituted or unsubstituted nucleus.
  • L is substituted or unsubstituted aryl-triyl, or substituted or unsubstituted heteroaryl-triyl to be.
  • the aryl-triyl group is a trivalent aryl group
  • the heteroaryl-triyl group is a trivalent heteroaryl group.
  • One or more substituents respectively introduced into the arylene group, heteroarylene group, aryl-triyl group, aryl-triyl group, and heteroaryl-triyl group of L are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 Alkyl group of C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 3 ⁇ C 40 alkylsilyl group, C 2 ⁇ C 40 alkyl
  • substituents are plural, they may be the same or different from each other.
  • L is bivalent or trivalent phenyl, biphenyl, naphthyl, indene, fluorenyl, carbazolyl, pyridine, pyrimidine, pyridazine, pyrazine, triazine, triazole, Selected from the group consisting of oxadiazole, thiadiazole, indole, benzimidazole, quinoline, isoquinoline, and quinoxaline, each independently of deuterium, halogen, cyano, nitro, alkyl group of C 1 to C 40 , C 6 ⁇ C 60 aryl group, nuclear atom 5 ⁇ 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 3 ⁇ C 40 alkylsilyl group, C 2 ⁇ C 40 alkyl boron group It may be substituted with one or more substituents selected from the group consisting of.
  • L may be selected from the group consisting of the following substituents C1 to C76, but is not limited thereto.
  • B is a substituted or unsubstituted carbazole group, or a substituent represented by Formula 3. At this time, when B is plural, they are different from each other or the same.
  • ring C is a 6-membered heterocycle containing CR 7 and N, a 6-membered cycle substituted with R 7 , or a 6-membered ring containing two N's It is a heterocyclic ring, It is a 6 membered ring preferably substituted with R ⁇ 7> .
  • X 3 and X 4 are each independently selected from the group consisting of O, S, Se, N (Ar 6 ), C (Ar 7 ) (Ar 8 ) and Si (Ar 9 ) (Ar 10 ), At least one of X 3 and X 4 is N (Ar 6 ). Preferably both X 3 and X 4 are N (Ar 6 ), or X 3 and X 4 are each independently N (Ar 6 ) or S.
  • Y 5 to Y 8 are the same as or different from each other, and each independently N or CR 8 , and preferably Y 5 to Y 8 are all CR 8 . At this time, when there are a plurality of CR 8 , they are different from each other or the same.
  • R 5 to R 8 and Ar 5 to Ar 8 is a single bond, and is connected to L of Chemical Formula 2.
  • each of R 1 to R 8 is independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C 1 to C 40 alkyl 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 group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted A substituted C 1 to C 40 alkyloxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 3 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C Arylsilyl group of 60 , substituted or unsubstituted C 1 ⁇ C 40 alkyl boron group
  • R 1 to R 8 are each independently hydrogen, C 6 ⁇ C 60 aryl group (e.g., phenyl, naphthyl, bisphenyl), 5 to nuclear atoms Preference is given to a 60 heteroaryl group (eg pyridine).
  • aryl group e.g., phenyl, naphthyl, bisphenyl
  • 5 to nuclear atoms Preference is given to a 60 heteroaryl group (eg pyridine).
  • One or more substituents respectively introduced to the phosphine group, the arylphosphine oxide group, and the arylamine group are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40 of, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkyl silyl group, C 6 ⁇ C
  • Ar 1 to Ar 10 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 3 to C 40 cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 3 to 40 nuclear atoms, substituted or unsubstituted C 6 -C 60 aryl groups, substituted or unsubstituted nuclear atoms having 5 to 60 heteroaryl groups , Substituted or unsubstituted C 1 ⁇ C 40 alkyloxy group, substituted or unsubstituted C 6 ⁇ C 60 aryloxy group, substituted or unsubstituted C 3 ⁇ C 40 alkylsilyl group, substituted or unsubstituted C 6 ⁇ C 60 arylsilyl group, substituted or unsubstituted C 1 ⁇ C 40 Alkyl
  • Ar 1 to Ar 10 may be each independently a substituted or unsubstituted C 6 ⁇ C 60 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms.
  • R 1 to R 8 , and Ar 1 to Ar 10 may be each independently selected from the group consisting of hydrogen, the following substituents S1 to S177, but is not limited thereto.
  • one of R 1 to R 4 , and Ar 1 to Ar 5 is a substituent represented by Formula 2, and one of R 5 to R 8 , and Ar 6 to Ar 10 is a single bond, Is connected to L.
  • the substituent represented by Chemical Formula 3 may be selected from the substituents represented by the following Chemical Formulas 3a to 3f, but is not limited thereto.
  • X 3 and X 4 are each independently selected from the group consisting of O, S, Se, N (Ar 6 ), C (Ar 7 ) (Ar 8 ) and Si (Ar 9 ) (Ar 10 );
  • R 5 to R 8 and Ar 6 to Ar 10 is a single bond and is connected to L of Formula 2;
  • R 5 to R 8 and Ar 6 to Ar 10 are as defined in Formula 1, respectively.
  • a plurality of R 7 are the same or different from each other, a plurality of R 8 is the same or different from each other.
  • Examples of the compound represented by Chemical Formula 1 according to the present invention include a compound represented by the following Chemical Formulas 4 to 9, but are not limited thereto.
  • X 1 and X 2 are each independently selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein X At least one of 1 and X 2 is N (Ar 1 );
  • R 1 to R 4 and Ar 1 to Ar 5 is a substituent represented by Formula 2;
  • R 1 to R 4 , and Ar 1 to Ar 5 are the same as defined in Chemical Formula 1.
  • Examples of the compound represented by Formula 1 according to the present invention include a compound represented by the following Formula 10, but is not limited thereto.
  • X 1 , Y 1 to Y 4 , Ring A, R 1 , R 2 , L, a and B are as defined in Formula 1, respectively,
  • a plurality of R 3 are the same or different from each other, a plurality of R 4 is the same or different from each other.
  • examples of the compound represented by Chemical Formula 1 include compounds represented by the following Chemical Formulas 11 to 16, but are not limited thereto.
  • X 1 , R 1 to R 4 , L, a and B are as defined in Formula 1, respectively,
  • the plurality of R 3 are the same or different from each other, the plurality of R 4 is the same or different from each other.
  • examples of the compound represented by Formula 1 according to the present invention include a compound represented by the following Formula 17, but is not limited thereto.
  • X 1 , X 3 , Y 1 to Y 8 , R 1 , R 2 , R 5 , R 6 , Ring A, Ring C, L and a are as defined in Formula 1, respectively.
  • examples of the compound represented by Chemical Formula 1 include a compound represented by the following Chemical Formulas 18 to 23, but are not limited thereto.
  • X 1 , X 3 , Y 5 to Y 8 , R 1 to R 6 , rings C, L and a are as defined in Formula 1, respectively,
  • the plurality of R 3 are the same or different from each other, the plurality of R 4 is the same or different from each other.
  • Specific examples of the compound represented by Chemical Formula 1 include a compound represented by Chemical Formula CH-1 to a compound represented by Chemical Formula CH-281, but are not limited thereto.
  • unsubstituted alkyl refers to a monovalent functional group obtained by removing a hydrogen atom 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 refers to 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. do. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, and the like, but are not limited thereto.
  • unsubstituted alkynyl 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. do. Examples thereof include ethynyl, 2-propynyl, and the like, but are not limited thereto.
  • unsubstituted cycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms.
  • cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • unsubstituted heterocycloalkyl 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, wherein at least one of the rings Carbon, preferably 1 to 3 carbons, is substituted with a hetero atom such as N, O or S.
  • a non-aromatic hydrocarbon saturated cyclic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the rings Carbon, preferably 1 to 3 carbons, is substituted with a hetero atom such as N, O or S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • unsubstituted aryl means the monovalent functional group obtained by removing a hydrogen atom from a C6-C60 aromatic hydrocarbon combined with a single ring or two or more rings. Two or more rings may be attached in a simple or fused form with one another. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.
  • unsubstituted heteroaryl 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 preferably at least one carbon in the ring, preferably Preferably 1 to 3 carbons are substituted with a heteroatom such as N, O, S or Se.
  • heteroaryl is interpreted that two or more rings may be attached in a simple attached (pendant) or fused (fused) form with each other, and further includes a condensed form 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 It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • unsubstituted alkyloxy means a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and is linear, branched or cyclic ( It is interpreted as including a 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 aryloxy means a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms.
  • aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • unsubstituted alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • unsubstituted arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms
  • "Unsubstituted arylamine” means an amine substituted with aryl having 6 to 60 carbon atoms.
  • unsubstituted alkyl boron means boron substituted with alkyl having 1 to 40 carbon atoms
  • unsubstituted aryl boron means boron substituted with aryl having 6 to 60 carbon atoms.
  • unsubstituted arylphosphine means phosphine substituted with aryl having 6 to 60 carbon atoms
  • unsubstituted arylphosphine oxide means phosphine substituted with aryl having 6 to 60 carbon atoms. Means oxide.
  • fused ring 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 according to the present invention may be synthesized according to a general synthetic method [ Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1) (preferably a compound represented by the formula 4 to 23).
  • the organic electroluminescent device is an anode; 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 Chemical Formula 1 (preferably, a compound represented by Chemical Formulas 4 to 23). It is characterized by including one or more.
  • the one or more organic material layers include a hole injection layer, a hole transport layer, and a light emitting layer, an electron transport layer, an electron injection layer, etc.
  • at least one organic material layer may include a compound represented by Chemical Formula 1.
  • at least one organic layer including the compound of Formula 1 may be a hole transport layer, a hole injection layer or a light emitting layer, more preferably a light emitting layer. If the compound of Formula 1 is included in the emission layer, the compound of Formula 1 may be used as a phosphorescent or fluorescent host material and / or dopant. As such, when the compound includes the organic electroluminescent device, the luminous efficiency, brightness, power efficiency, thermal stability, and lifetime of the device may be improved.
  • the organic EL device structure according to the present invention is not particularly limited, and a non-limiting example 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.
  • at least one of the hole injection layer, the hole transport layer, and the light emitting layer may include at least one compound represented by Chemical Formula 1.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between an electrode and an organic material layer.
  • the organic electroluminescent device according to the present invention is formed by using other materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by the formula (1). Can be produced.
  • 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 or glass plate, metal plate, plastic film or sheet may be used as the substrate usable in the present invention.
  • 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 and polyaniline; Or carbon black, but is 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; 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, conventional materials known in the art may be used.
  • Preparation Example The same procedure as in ⁇ Step 1> of Preparation Example 1, except that 6-bromo-1H-indole (25 g, 0.128 mol) was used instead of 5-bromo-1H-indole used in ⁇ Step 1>. The procedure was followed to obtain 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole.
  • Step 1 of Preparation Example 4> instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole used in ⁇ Step 2> of Preparation Example 1
  • Preparation Example 1 except that 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22 g, 90.49 mmol) obtained in The procedure of step 2> was followed to obtain 7- (2-nitrophenyl) -1H-indole.
  • 2,4-dibromo-1-nitrobenzene (21.11 g, 75.41 mmol) was used instead of 1-bromo-2-nitrobenzene used in ⁇ Step 2> of Preparation Example 1, and 5- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole instead of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (22 g, 90.49 mmol) was used in the same manner as in ⁇ Step 2> of Preparation Example 1 to obtain 6- (5-bromo-2-nitrophenyl) -1H-indole.
  • 6-chloro-1H-indole 25 g, 0.13 mol was used instead of 5-bromo-1H-indole used in ⁇ Step 1> of Preparation Example 18, and 6-chloro-1H-indole and bromobenzene (23.55) instead of Iodobenzene. g, 0.15 mol), except that 6-chloro-2-phenyl-1H-indole was obtained in the same manner as in ⁇ Step 1> of Preparation Example 20 18.
  • 6-chloro-2-phenyl-1H-indole (15 g, 55.12) obtained in ⁇ Step 1> of Preparation Example 19 instead of 5-bromo-2-phenyl-1H-indole used in ⁇ Step 2> of Preparation Example 18 mmol), except that 6- (2-nitrophenyl) -2-phenyl-1H-indole was obtained in the same manner as in ⁇ Step 2> of Preparation Example 18.
  • 6-chloro-1H-indole 25 g, 0.17 mol
  • bromobenzene 31.19 g, 0.20 mol
  • Pd (OAc) 2 (1.86 g, 5 mol)
  • Triphenylphosphine (2.17 g, 5 mol%)
  • K 2 CO 3 68.64 g, 0.50 mol
  • 1,4-dioxane 300 ml
  • 6-chloro-3-phenyl-1H-indole (15 g, 55.12) obtained in ⁇ Step 1> of Preparation Example 20 instead of 5-bromo-2-phenyl-1H-indole used in ⁇ Step 2> of Preparation Example 18 mmol), except that 6- (2-nitrophenyl) -3-phenyl-1H-indole was obtained in the same manner as in ⁇ Step 2> of Preparation Example 20 18.
  • a compound Inv-2 (3) was obtained by the same procedure as in Synthesis Example 1, except that Compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 1. 1.64 g, yield: 54%) was obtained.
  • a compound Inv-3 was prepared in the same manner as in Synthesis Example 1, except that Compound IC-6 (3 g, 10.63 mmol) obtained in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 1. 1.82 g, yield: 60%) was obtained.
  • a compound Inv-4 (Ind-4) was prepared in the same manner as in Synthesis Example 1, except that Compound IC-5 (3 g, 10.63 mmol) obtained in Preparation Example 3 was used instead of Compound IC-1 used in Synthesis Example 1. 1.52 g, yield: 50%) was obtained.
  • a compound Inv-4 (Ind-4) was prepared in the same manner as in Synthesis Example 1, except that Compound IC-2 (3 g, 10.63 mmol) obtained in Preparation Example 1 was used instead of Compound IC-1 used in Synthesis Example 1. 1.34 g, yield: 44%) was obtained.
  • a compound Inv-6 was prepared by the same procedure as in Synthesis Example 1, except that Compound IC-4 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 1. 1.4 g, yield: 46%).
  • a compound Inv-18 was prepared by the same procedure as in Synthesis Example 9, except that Compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 9. 1.76 g, yield: 47%).
  • a compound Inv-20 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 11. 1.67 g, yield: 53%) was obtained.
  • a compound Inv-23 (Ind-23) was obtained by the same procedure as in Synthesis Example 14, except that Compound IC-3 (3 g, 10.63 mmol) obtained in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 14. 1.73 g, yield: 57%) was obtained.
  • a compound Inv-40 was prepared in the same manner as in Synthesis Example 1, except that Compound IC-20 (3.80 g, 10.63 mmol) obtained in Preparation Example 18 was used instead of Compound IC-1 used in Synthesis Example 1. 2.62 g, yield: 71%).
  • Compound Inv-41 (Complete Example 1) was carried out in the same manner as in Synthesis Example 1, except that Compound IC-16 (4.61 g, 10.63 mmol) obtained in Preparation Example 16 was used instead of Compound IC-1 used in Synthesis Example 1. 1.77 g, yield: 41%).
  • the compound Inv-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a commonly known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out. The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • m-MTDATA, TCTA, Ir (ppy) 3 , CBP, and BCP used in device fabrication are as follows.
  • Example 1 Except for using the compounds Inv-2 to Inv-57 synthesized in Synthesis Examples 2 to 57 instead of the compound Inv-1 used as a host material in the formation of the light emitting layer in Example 1, the same as in Example 1 To an organic EL device.
  • An 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 in forming the emission layer in Example 1.
  • the structure of CBP used is as follows.
  • Example 1 Sample Host Driving voltage (V) Current efficiency (cd / A) Example 1 Compound Inv-1 6.68 41.1 Example 2 Compound Inv-2 6.68 41.2 Example 3 Compound Inv-3 6.85 40.9 Example 4 Compound Inv-4 6.83 41.3 Example 5 Compound Inv-5 6.85 39.2 Example 6 Compound Inv-6 6.89 41.7 Example 7 Compound Inv-7 6.91 38.9 Example 8 Compound Inv-8 6.67 40.9 Example 9 Compound Inv-9 6.65 42.1 Example 10 Compound Inv-10 6.63 41.1 Example 11 Compound Inv-11 6.65 39.1 Example 12 Compound Inv-12 6.66 40.3 Example 13 Compound Inv-13 6.7 41.2 Example 14 Compound Inv-14 6.73 39.8 Example 15 Compound Inv-15 6.75 39.3 Example 16 Compound Inv-16 6.88 39.4 Example 17 Compound Inv-17 6.88 38.8 Example 18 Compound Inv-18 6.72 41.3 Example 19 Compound Inv-19 6.69 41.3 Example 20 Compound Inv-20 6.69 38.8 Example 21 Compound Inv
  • the green organic EL elements (the organic ELs produced in Examples 1 to 57, respectively) using the compounds (compounds Inv-1 to Inv-57) according to the present invention as the light emitting layer material (host material of the light emitting layer) It can be seen that the device exhibits excellent performance in terms of current efficiency and driving voltage compared to the conventional green organic EL device (organic EL device manufactured in Comparative Example 1) using the host material CBP.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out.
  • the substrate was transferred to a vacuum evaporator.
  • DS-HIL Doosan Co., Ltd.
  • ⁇ -NPB N , which is a hole transport material on the hole injection layer
  • N- di (naphthalene-1-yl) -N , N- diphenylbenzidine) was vacuum deposited to a thickness of 150 kPa to form a hole transport layer.
  • m-CP (1,3-di (9H-carbazol-9-yl) benzene) was used as the host material and 6% of the compound Inv-15 synthesized in Synthesis Example 1 was doped as a dopant.
  • the light emitting layer was formed by vacuum deposition on the hole transport layer to a thickness of.
  • an electron transporting layer was formed by vacuum depositing Alq 3 , which is an electron transporting material, to a thickness of 250 kPa on the light emitting layer, and then an electron injection layer was formed by depositing LiF, which is an electron injection material, on the electron transporting layer, having a thickness of 10 kW.
  • Alq 3 which is an electron transporting material
  • LiF which is an electron injection material
  • aluminum was vacuum deposited to a thickness of 2000 kPa on the electron injection layer to form a cathode, thereby manufacturing an organic EL device.
  • ⁇ -NPB and m-CP used are as follows.
  • Example 58 Compound Inv-24, Inv-29, Inv-30, Inv-31, Inv-32, Inv-58, Inv-59, Inv-60 instead of Compound Inv-15 used as dopants in the formation of the emission layer in Example 58 Except for each use, the organic electroluminescent device was manufactured in the same manner as in Example 58.
  • Example 58 except that DS-H522 (Doosan Corporation) was used instead of m-CP used as a host material in forming the light emitting layer, and C-545T was used instead of compound Inv-15 used as a dopant material.
  • the organic electroluminescent device was manufactured in the same manner as in Example 58.
  • Example 58 Compound Inv-15 6.1 32.5
  • Example 59 Compound Inv-24 6.3 31.7
  • Example 60 Compound Inv-29 6.2 31.9
  • Example 61 Compound Inv-30 6.0 32.2
  • Example 62 Compound Inv-31 5.5 32.9
  • Example 63 Compound Inv-32 5.9 32.3
  • Example 64 Compound Inv-58 5.8 33.1
  • Example 65 Compound Inv-59 5.7 33.5
  • Example 66 Compound Inv-60 5.6 32.0 Comparative Example 2 C-545T 6.8 23.0
  • the compounds according to the present invention (Inv-15, Inv-24, Inv-29, Inv-30, Inv-31, Inv-32, Inv-58, Inv-59, Inv-60)
  • the green fluorescent organic EL device (the organic EL device manufactured in each of Examples 58 to 66) using as a light emitting layer material (the dopant of the light emitting layer) is a green fluorescent organic EL device using the conventional dopant C-545T (organic EL of Comparative Example 2). Element), it can be seen that it shows excellent performance in terms of current efficiency and driving voltage.

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Abstract

La présente invention concerne un nouveau composé organique ayant d'excellentes capacités d'injection de trous, de transport de trous et d'émission de lumière, et un élément électroluminescent organique contenant le composé dans au moins une couche organique de façon à améliorer les caractéristiques de rendement d'émission de lumière, de tension de commande, de durée de vie, etc.
PCT/KR2013/007821 2012-09-19 2013-08-30 Composé organique et élément électroluminescent le comportant WO2014046392A1 (fr)

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CN106892901A (zh) * 2017-04-21 2017-06-27 瑞声光电科技(常州)有限公司 三嗪化合物及发光器件
US10593888B2 (en) 2017-02-23 2020-03-17 Samsung Display Co., Ltd. Polycyclic compound and organic light-emitting device including the same
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KR20200110506A (ko) * 2019-03-13 2020-09-24 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자
KR20200118329A (ko) 2019-04-05 2020-10-15 삼성디스플레이 주식회사 유기 전계 발광 소자 및 유기 전계 발광 소자용 화합물

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