WO2015190718A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2015190718A1
WO2015190718A1 PCT/KR2015/005080 KR2015005080W WO2015190718A1 WO 2015190718 A1 WO2015190718 A1 WO 2015190718A1 KR 2015005080 W KR2015005080 W KR 2015005080W WO 2015190718 A1 WO2015190718 A1 WO 2015190718A1
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group
substituted
unsubstituted
formula
aryl
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PCT/KR2015/005080
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English (en)
Korean (ko)
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김태형
박호철
엄민식
김영배
김회문
박성진
백영미
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주식회사 두산
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials

Definitions

  • the present invention relates to an organic electroluminescent device comprising at least one organic material layer.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • a light emitting material mixed with a host material and a dopant material may be used.
  • 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.
  • metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and CBP is known as a phosphorescent host material.
  • the conventional materials do not have a satisfactory level in terms of lifespan in the organic electroluminescent device because of the low glass transition temperature and poor thermal stability. Therefore, there is a demand for the development of an organic EL device including a light emitting material having excellent performance.
  • an object of the present invention is to provide an organic electroluminescent device having improved characteristics such as driving voltage, luminous efficiency and lifetime.
  • the present invention 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 includes a first host and a second host, wherein the first host is represented by Formula 1 below. It is a compound, wherein the second host provides an organic electroluminescent device, characterized in that the compound represented by the formula (2).
  • R a to R d are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 40 alkyl group, and a substituted or unsubstituted C 6 to C 60 aryl group Selected,
  • X 1 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
  • Y 1 to Y 4 are the same as or different from each other, and each independently N or C (R 1 ), wherein when there are a plurality of C (R 1 ), a plurality of R 1 are the same or different, and each of them is adjacent to a group; Can form condensed rings;
  • X 2 and X 3 are the same or different from each other, and each independently N or C (R 2 ), wherein when there are a plurality of C (R 2 ), a plurality of R 2 are each the same or different, and they are condensed with adjacent groups May form a ring;
  • R 1 to R 2 and Ar 1 to Ar 5 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C 1 to C 40
  • an alkyl group alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group
  • an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, a phosphine group, a phosphine oxide group and an arylamine group are substituted, each independently deuterium, halogen group, cyano group, nitro group, amino group, C 1 a ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ⁇ C 40 of the An aryl group,
  • the organic material layer including the first host and the second host is preferably a phosphorescent layer.
  • the light emitting layer preferably includes a metal complex compound dopant.
  • the organic electroluminescent device of the present invention comprises an organic material layer comprising a first host and a second host, by mixing the compound represented by the formula (1) and the compound represented by the formula (2) as the first host and the second host, respectively.
  • the driving voltage, luminous efficiency, and lifespan of the device can be improved. Therefore, when manufacturing a display panel using the organic electroluminescent device of the present invention, it is possible to provide a display panel with improved performance and lifespan.
  • the organic electroluminescent device of 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 a first host and a second host.
  • the first host is a compound represented by Chemical Formula 1
  • the second host is a compound represented by Chemical Formula 2 below.
  • the compound represented by Chemical Formula 1, which is used as the first host in the present invention, substitutes hydrogen, deuterium, an alkyl group of C 1 to C 40 or an aryl group of C 6 to C 60 to a 3,3'-biscarbazole base skeleton. Can be.
  • the carbazole skeleton has the characteristics of an electron donating group having high electron donating and hole transporting properties. Therefore, as shown in Formula 1, when two carbazole skeletons are included in the molecule, the carbazole skeleton has a high hole transporting property, and when the carbazole skeleton is one, the molecular weight is significantly increased to have high thermal stability.
  • the basic skeleton in the form of 3,3 'bonded biscarbazole is the main binding site of carbazole, and can firmly connect two carbazoles to enhance the thermal and electrical stability of the molecule itself.
  • R a to R d are the same as or different from each other, and each independently hydrogen, deuterium, an alkyl group of C 1 to C 40 and an aryl group of C 6 to C 60 . Selected from the group. More specifically, R a to R d are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen, methyl, ethyl, propyl, iso-propyl, t-butyl, phenyl, biphenyl, and the like. .
  • Alkyl and aryl groups which are the aforementioned substituents, have electron donating and hole transporting properties, thereby enhancing the characteristics of the electron donating group in the molecule.
  • R a to R d are each independently preferably a phenyl group, and the bonding position of the phenyl group is not particularly limited and is not limited.
  • the compound represented by the formula (1) according to the present invention can be more embodied in a compound group consisting of the following formula. However, this is not particularly limited.
  • the compound represented by Formula 2 which is used as the second host in the present invention, is a condensed carbon ring or a condensed heterocyclic moiety, preferably a condensed heterocyclic moiety, connected to an indole-based skeleton, and is energized by various substituents.
  • the level is adjusted to have a wide energy band gap (sky blue to red). Accordingly, when the compound represented by Formula 2 is used as the second host of the organic material layer of the organic light emitting device, the light emitting (phosphorescence) characteristics of the organic light emitting device are improved, and the electron and / or hole transporting ability and the light emitting ability are improved. Can be.
  • the compound represented by Formula 2 various aromatic rings are bonded to the indole-based backbone as a substituent to significantly increase the molecular weight of the compound. Therefore, the glass transition temperature (Tg) is improved and thereby may have a higher thermal stability than the conventional CBP.
  • Tg glass transition temperature
  • the whole molecule has a bipolar characteristic and can enhance the binding force between holes and electrons. Can be represented.
  • Y 1 to Y 4 are the same as or different from each other, and each independently N or C (R 1 ).
  • R 1 when there are a plurality of C (R 1 ), a plurality of R 1 may be the same or different, and each of them may form a condensed ring with an adjacent group.
  • X 2 and X 3 are the same as or different from each other, and are each independently N or C (R 2 ). In this case, when there are a plurality of C (R 2 ), a plurality of R 2 are the same or different, and they may form a condensed ring with an adjacent group.
  • condensed ring with an adjacent group (adjacent)', two or more adjacent plural substituents are bonded to each other condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring, or condensation known in the art It means forming a heteroaromatic ring.
  • the compound represented by Chemical Formula 2 may be more specific as A-1 to A-24, but is not limited thereto.
  • R 2 , Y 1 to Y 4 and Ar 1 to Ar 5 are the same as defined in Formula 2 above.
  • the case of A-1 to A-6 is preferable.
  • Chemical Formula 2 of the present invention may be used alone as the structure of Chemical Formula 2, or Chemical Formula 2 may be combined with the following Chemical Formula 3 or Chemical Formula 4 to form a condensation structure.
  • Y 1 to Y 4 in Formula 2 are a plurality of C (R 1 )
  • one of Y 1 and Y 2 , Y 2 and Y 3 or Y 3 and Y 4 is a condensed ring with Formula 3 Can be formed.
  • a plurality of R 1 may be the same or different, respectively.
  • Y 1 to Y 4 of Chemical Formula 2 may be combined with X 9 and X 10 of Chemical Formula 3.
  • a plurality of R 2 may be combined with each of the following formula (3) or formula (4) to form a condensed ring.
  • it may be combined with Formula 4 to form a condensed ring.
  • X 2 and X 3 of Formula 2 may combine with Y 11 to Y 14 of Formula 4 to form a condensed ring.
  • Y 5 to Y 14 are the same as or different from each other, and each independently N or C (R 3 ), and in the case where there are a plurality of C (R 3 ), a plurality of R 3 are the same as or different from each other, and they are represented by Formula 2 above.
  • R 3 N or C
  • R 3 condensed ring
  • X 4 is the same as X 1 described above, wherein a plurality of Ar 1 to Ar 5 are the same or different, respectively.
  • R 3 non-forming a condensed ring with Formula 2 is each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C 1 ⁇ C 40 alkyl, substituted or Unsubstituted C 2 -C 40 alkenyl group, substituted or unsubstituted C 2 -C 40 alkynyl group, substituted or unsubstituted C 3 -C 40 cycloalkyl group, substituted or unsubstituted nuclear atom 3 to 40 heterocycloalkyl groups, substituted or unsubstituted C 6 to C 60 aryl groups, substituted or unsubstituted heteroaryl groups having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 40 alkyloxy groups , Substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 1 -C 40 alkylsilyl group,
  • an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, phosphine group, a phosphine oxide group, and aryl amine groups are each independently selected from deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C case be substituted 2 or an alkynyl group of C 40, C 3 ⁇ C 40 cycloalkyl group, a number of the aryl group, the nucleus of atoms of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 40 of from 5 to 40 heteroaryl group, C 1 ⁇ C
  • the compound formed by condensation of Chemical Formula 2 and Chemical Formula 3 may be further embodied as a compound represented by Chemical Formulas 2a to 2f.
  • X 1 to X 4 and Y 1 to Y 8 are the same as defined in Chemical Formula 2 and Chemical Formula 3, respectively.
  • Y 1 to Y 4 to form a condensed ring ratio ( ⁇ ) is N or C (R 1), wherein if the Y 1 to Y 4 are both C (R 1) is preferred.
  • the Y 5 to Y 8 is a case of N or C (R 3) a, wherein Y 5 to Y 8 are both C (R 3) are preferred.
  • a plurality of R 1 and R 3 are the same or different, respectively.
  • Compounds of the present invention in which Formula 2 and Formula 3 are condensed may be more specifically formulated into a compound group consisting of Formulas B-1 to B-30. However, this is not particularly limited.
  • Ar 1 is a substituted or unsubstituted C 6 ⁇ C 40 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,
  • R 1 to R 3 are 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, or a substituted or unsubstituted nuclear atom 5 to 40 It is preferable when it is a heteroaryl group of.
  • Formulas B-1 to B-30 having a structure formed by condensation of Formulas 2 and 3 include one or more condensed indole or condensed carbazole moieties.
  • the compound formed by condensation of Chemical Formula 2 and Chemical Formula 4 may be further embodied as a compound represented by Chemical Formula 2g to 2n.
  • X 1 , X 4 and Y 1 to Y 14 are the same as defined in Formula 2 and Formula 4, respectively.
  • X 1 and X 4 are each independently O, S or N (Ar 1 ), it is more preferable that both X 1 and X 4 is N (Ar 1 ), wherein a plurality of Ar 1 Are the same or different, respectively.
  • Y 1 to Y 4 are each independently N or C (R 1 ), and preferably Y 1 to Y 4 are all C (R 1 ), wherein a plurality of R 1 are the same or different.
  • Y 5 to Y 14 are each independently N or C (R 3 ), and preferably Y 5 to Y 14 are all C (R 3 ), wherein a plurality of R 3 are the same or different.
  • Ar 1 and R 1 to R 3 are the same as defined in the above formula (2) and (4).
  • the compound represented by any one of Formulas 2a to 2n used as the second host, X 1 and X 4 are each independently It is preferred that it is N (Ar 1 ) or S. That is, it is preferable that X 1 is N (Ar 1 ) and X 4 is S, X 1 is S and X 4 is N (Ar 1 ), or both X 1 and X 4 are N (Ar 1 ).
  • Ar 1 is preferably a substituted or unsubstituted C 6 ⁇ C 60 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms
  • Ar 2 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 (specifically, a methyl group) or a substituted or unsubstituted C 6 to C 60 aryl group (specifically Phenyl group) is preferable.
  • Ar 1 is preferably a substituent represented by the following formula (5) or a phenyl group.
  • L is selected from the group consisting of a single bond, a substituted or unsubstituted C 6 ⁇ C 18 arylene group and a substituted or unsubstituted heteroarylene group having 5 to 18 nuclear atoms,
  • Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 11 ), wherein at least one of Z 1 to Z 5 is N,
  • R 11 s When there are a plurality of R 11 s , they are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted substituted or unsubstituted C 1 to C 40 alkyl group, substituted or Unsubstituted C 2 -C 40 alkenyl group, substituted or unsubstituted C 2 -C 40 alkynyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted nuclear atom 5 to 60 heteroaryl groups, substituted or unsubstituted C 6 -C 60 aryloxy groups, substituted or unsubstituted C 1 -C 40 alkyloxy groups, substituted or unsubstituted C 3 -C 40 cycloalkyl groups, Substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms
  • arylene group, heteroarylene group, alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine 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, 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 5 to 60 heteroaryl group, C 6 ⁇ C 40 60 Aryloxy group, C 1 ⁇ C 40 Alkyl Oxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl
  • L is preferably a single bond, a phenylene group or a biphenylene group.
  • * means a part bonded to the formula (2), when two or more of Z 1 to Z 5 is C (R 11 ), a plurality of R 11 may be the same or different from each other.
  • the substituent represented by the formula (5) is preferably selected from a substituent group consisting of a structure represented by the following C-1 to C-15.
  • R 12 is hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C 1 ⁇ C 40 alkyl group, substituted or unsubstituted C 2 ⁇ C 40 alkenyl group, substituted or unsubstituted C 2 ⁇ C 40 alkynyl group, substituted or unsubstituted C 3 to C 40 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C 6 to C 60 aryl group, Substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 1 to C 40 alkyloxy group, substituted or unsubstituted C 6 ⁇ C 60 arylamine group, substituted or unsubstituted C 1 ⁇ C 40 Alky
  • n is an integer of 1-4.
  • Ar 1 to Ar 5 and R 1 to R 3 may be each independently selected from a substituent group (S1-S206) consisting of hydrogen or the following substituents (functional groups). However, this is not particularly limited.
  • alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl. Etc. can be mentioned.
  • Alkenyl 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 double bonds. Examples thereof include vinyl and allyl. ), Isopropenyl, 2-butenyl, and the like.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl, 2- Propanyl (2-propynyl) etc. are mentioned.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
  • a form in which two or more rings are pendant or condensed with each other may also be included.
  • aryls include phenyl, naphthyl, phenanthryl, anthryl and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may also be included, and may also include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furany
  • Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and includes a linear, branched or cyclic structure
  • alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Substituted with a hetero atom such as Se.
  • heterocycloalkyl include morpholine, piperazine and the like.
  • Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the organic electroluminescent device of the present invention configured as described above may have a long life because at least one of the plurality of organic material layers may balance holes and electrons injected into the device including the first host and the second host. have.
  • the mixing ratio of the first host and the second host is not particularly limited when the organic layer is manufactured.
  • the first host and the second host may be mixed in a weight ratio of 1:99 to 99: 1. At this time, it is preferable that the use ratio of the first host is higher.
  • the light emitting layer may be a single light emitting layer, or may have a plurality of light emitting layers to implement a mixed color thereof. More specifically, in the present invention, a plurality of light emitting layers may be sequentially stacked between the hole transport layer and the electron transport layer to implement a mixed color thereof when voltage and current are applied.
  • the stacked organic electroluminescent device of the present invention having a plurality of light emitting layers including a plurality of light emitting layers or heterogeneous materials in series between the hole transport layer and the electron transport layer as described above may realize a mixed color when voltage and current are applied or a plurality of light emitting layers.
  • the light emission efficiency can be increased by the number of light emitting layers.
  • the organic material layer of the present invention including the first host and the second host is preferably a light emitting layer, wherein the light emitting layer of the present invention may include a dopant together with the first host and the second host.
  • the material that can be used as the dopant included in the light emitting layer can be used without limitation conventional dopant components known in the art, it is preferable to use a metal complex compound containing iridium (Ir) as an example.
  • the method of manufacturing the light emitting layer including the first host, the second host, and the dopant described above may be manufactured without particular limitation in accordance with methods known in the art.
  • two preferable embodiment which manufactures the said light emitting layer is illustrated below, it is not specifically limited to this.
  • a first method of the above two embodiments is a co-deposition method of placing a first host and a second host in a first heat source and a second heat source, respectively, and placing a dopant in a third heat source to simultaneously apply heat to form a light emitting layer. .
  • a second host having high hole mobility and good hole injection efficiency is placed in the first heat source, and electron mobility is located in the second heat source.
  • a method of co-depositing at a proper ratio by placing a second host having a high c) and having a good electron injection efficiency and controlling a dopant of a third heat source and an evaporation rate per second.
  • the number of co-deposited hosts may be two or more according to the characteristics of the light emitting layer.
  • the amount of the first host, the second host, and the dopant is not particularly limited.
  • the first host, the second host, and the first host and the second host may be 70 to 99% by weight and the dopant to 1 to 30% by weight.
  • the first host and the second host used for forming the light emitting layer are mixed at an appropriate ratio, placed in one heat source, and heat is removed. It is a co-deposition method which adds and forms a light emitting layer.
  • This second method has the advantage of reducing the mixing ratio error that occurs when using more than one host, and can form a light emitting layer with a small number of heat sources.
  • the amount of the first host, the second host, and the dopant is not particularly limited.
  • the first host, the second host, and the dopant may be used in a range of 70 to 99% by weight, and the dopant to 1 to 30% by weight. Specifically, it is preferable to use 80 to 95 wt% of the first host and the second host, and 5 to 20 wt% of the dopant.
  • the material usable as the anode included in the organic electroluminescent device of the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al and SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; And carbon black.
  • metals such as vanadium, chromium, copper, zinc, gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al and SnO 2 : Sb
  • the material which can be used as the cathode included in the organic electroluminescent device of the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead Metals such as these, alloys thereof, and multilayered structure materials such as LiF / Al and LiO 2 / Al.
  • the structure of the organic EL device of the present invention is not particularly limited, but a non-limiting example is a structure in which a substrate, an anode, an organic material layer (hole injection layer-> hole transport layer-> light emitting layer-> electron transport layer) and a cathode are sequentially stacked.
  • a substrate, an anode, an organic material layer (hole injection layer-> hole transport layer-> light emitting layer-> electron transport layer) and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1 as a first host.
  • the electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic EL device according to the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the anode and cathode and the organic material layer.
  • the organic electroluminescent device of the present invention uses conventional materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the first host and the second host. Another organic material layer can be formed.
  • at least one layer eg, the light emitting layer
  • Another organic material layer can be formed.
  • the substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, but non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
  • 2,4-dibromoaniline 25.09 g, 0.1 mol
  • methylene chloride 100 ml
  • Benzoyl chloride 11.6 mL, 0.1mol
  • pyridine 1.62 mL, 0.02 mol
  • N- (2,4-dibromophenyl) benzamide (25.1 g, 71.0 mmol), K 2 CO 3 (19.6 g, 142 mmol) and DMSO (710 ml) were mixed under nitrogen stream and stirred at 140 ° C. for 1.5 h.
  • 6-bromo-2-phenylbenzo [d] oxazole (14.8 g, 54.0 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi under nitrogen stream (1,3,2-dioxaborolane) (15.1 g, 59.4 mmol), Pd (dppf) Cl 2 (6.24 g, 5.40 mmol), KOAc (15.25 g, 0.162 mol) and 1,4-Dioxane (280 ml) Mix and stir at 130 ° C. for 12 h.
  • N- (2,4-dibromophenyl) benzamide (26.62 g, 0.075 mol) obtained in ⁇ Step 1> of Preparation Example 3 was added to the reactor, toluene (300 ml) was added thereto, followed by stirring. Lawesson's reagent (22.92 g, 0.053 mol) was added dropwise to the reactor, followed by mixing and stirring at 110 ° C. for 4 hours.
  • N- (2,4-dibromophenyl) benzothioamide (26.35 g, 71.0 mmol), K 2 CO 3 (19.63 g, 142 mmol) and DMSO (710 ml) obtained in ⁇ Step 1> of Preparation Example 8 under nitrogen stream were prepared. Mix and stir at 140 ° C. for 1.5 h.
  • 6-bromo-2-phenylbenzo [d] thiazole (15.66 g, 54.0 mmol) was used instead of 6-bromo-2-phenylbenzo [d] oxazole, and was synthesized in the same manner as in Step 3 of Preparation Example 3 above. , 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole (14.02 g, yield 77%) was obtained.
  • step 3 of Preparation Example 1 Same as step 3 of Preparation Example 1, except that 5- (2-nitrophenyl) -1H-benzo [d] imidazole (5.2 g, 21.75 mmol) was used instead of 5- (2-nitrophenyl) -1H-indole.
  • the synthesis was carried out to obtain 5- (2-nitrophenyl) -1-phenyl-1H-benzo [d] imidazole (6.84 g, 71% yield).
  • 6-bromo-1H-indole instead of 5-bromo-1H-indole, 6- (4,4,5,5-tetramethyl was carried out in the same manner as in ⁇ Step 1> of Preparation Example 1 -1,3,2-dioxaborolan-2-yl) -1H-indole was obtained.
  • 6- (2-nitrophenyl) -1H-indole instead of 5- (2-nitrophenyl) -1H-indole, 6- (2 -nitrophenyl) -1-phenyl-1H-indole was obtained.
  • IC-6 (3.20 g, 7.31 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-), which are the compounds prepared in Preparation Example 6 under nitrogen stream dioxaborolan-2-yl) phenyl) -1,3,5-triazine (3.81 g, 8.77 mmol), NaOH (0.87 g, 21.93 mmol), Pd (PPh 3 ) 4 (0.25 g, 0.21 mmol) and 1,4 -dioxane, H 2 O (30 ml, 8 ml) was mixed and stirred at 100 ° C. for 12 h. After completion of the reaction, the mixture was extracted with ethyl acetate and filtered with MgSO 4 . After removing the solvent of the organic layer filtered to obtain the target compound Com-14 (2.67 g, 55% yield) using column chromatography.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwashin Tech
  • M-MTDATA 60 nm using the C-1 to C-7 as the first host and the compounds represented by the Com-1 to Com-16 as the second host, respectively, on the prepared ITO transparent substrate.
  • / TCTA 80 nm) / 90% of the first and second host + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al ( 200 nm) was laminated in order to fabricate an organic EL device.
  • the structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP used are as follows, and the mixing ratio of the first host and the second host is 7: 3.
  • Example 1 On the prepared ITO transparent substrate, m-MTDATA (60 nm) / TCTA (80 nm) / 90% of C-3 as the first host and the compound represented by the Com-1 as the second host Organic electroluminescence by stacking the first host and the second host + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) The device was produced.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that 90% CBP + 10% Ir (ppy) 3 was used to form the emission layer. At this time, the structure of the CBP used is as follows.
  • An organic EL device was manufactured in the same manner as in Example 1, except that 90% of the second host (Com-1) + 10% Ir (ppy) 3 was used to form the emission layer.
  • An organic EL device was manufactured in the same manner as in Example 1, except that 90% of the first host (C-3) + 10% Ir (ppy) 3 was used to form the emission layer.
  • Example 1 Sample Host Usage Rate Driving voltage (V) Current efficiency (cd / A) Example 1 70% C-1 + 30% Com-1 6.10 42.9 Example 2 70% C-1 + 30% Com-2 6.15 42.8 Example 3 70% C-1 + 30% Com-3 6.15 42.8 Example 4 70% C-1 + 30% Com-4 6.10 42.9 Example 5 70% C-1 + 30% Com-5 6.10 42.5 Example 6 70% C-1 + 30% Com-6 6.25 42.6 Example 7 70% C-1 + 30% Com-7 6.15 42.5 Example 8 70% C-1 + 30% Com-8 6.20 42.9 Example 9 70% C-1 + 30% Com-9 6.25 43.0 Example 10 70% C-1 + 30% Com-10 6.20 42.7 Example 11 70% C-1 + 30% Com-11 6.25 42.9 Example 12 70% C-1 + 30% Com-12 6.35 42.5 Example 13 70% C-1 + 30% Com-13 6.30 43.2 Example 14 70% C-1 + 30% Com-14 6.10 43.0 Example 15 70% C-1 + 30% Com-15 6.25 42.9 Example 16 70% C-2 + 30% Com-1 6.25 43.1 Example 17 70% C-2 + 30% Com-2 6.20 42.9 Example 18 70% C-2 + 30% Com
  • the organic electroluminescent device of Examples 1 to 81 using the light emitting layer including the first host and the second host is Comparative Example 1 using a conventional CBP; Or compared with the organic electroluminescent device of Comparative Example 2 and Comparative Example 3 using the light emitting layer containing Com-1 and C-3 as a single host material, it was confirmed that the excellent performance in terms of current efficiency and driving voltage. .

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant une anode, une cathode, et une ou plusieurs couches organiques intercalées entre l'anode et la cathode, au moins une des couches organiques comprenant un premier hôte et un second hôte.
PCT/KR2015/005080 2014-06-09 2015-05-21 Dispositif électroluminescent organique WO2015190718A1 (fr)

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KR20160012409A (ko) * 2014-07-24 2016-02-03 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
US20160322583A1 (en) * 2013-12-27 2016-11-03 Doosan Corporation Organic electroluminescent device
EP3185331A1 (fr) * 2015-12-22 2017-06-28 Samsung Display Co., Ltd. Dispositif électroluminescent organique
EP3188277A1 (fr) * 2015-12-29 2017-07-05 Samsung Display Co., Ltd. Dispositif électroluminescent organique
CN107275496A (zh) * 2016-04-07 2017-10-20 三星显示有限公司 有机发光器件
US10230053B2 (en) * 2015-01-30 2019-03-12 Samsung Display Co., Ltd. Organic light-emitting device
US10280171B2 (en) 2016-05-31 2019-05-07 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11
EP3643761A1 (fr) 2018-10-25 2020-04-29 Idemitsu Kosan Co., Ltd. Composition, matériau pour dispositif électroluminescent organique, film de composition, dispositif d'électroluminescence organique et dispositif électronique
CN111406060A (zh) * 2018-02-02 2020-07-10 株式会社Lg化学 杂环化合物和包含其的有机发光元件
US10954243B2 (en) 2018-05-02 2021-03-23 Navire Pharma, Inc. Substituted heterocyclic inhibitors of PTPN11
US11104675B2 (en) 2018-08-10 2021-08-31 Navire Pharma, Inc. PTPN11 inhibitors
US11168093B2 (en) 2018-12-21 2021-11-09 Celgene Corporation Thienopyridine inhibitors of RIPK2
WO2022178693A1 (fr) * 2021-02-23 2022-09-01 苏州大学 Procédé de préparation d'un composé benzothiazole à l'aide de n-(2-bromophényl)thioamide sous activation à la lumière visible
CN115043852A (zh) * 2022-07-26 2022-09-13 武汉天马微电子有限公司 一种苯并恶唑衍生物及其电致发光的应用
US11466017B2 (en) 2011-03-10 2022-10-11 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11
US11617290B2 (en) 2015-12-22 2023-03-28 Samsung Display Co., Ltd. Organic light-emitting device
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JP7187152B2 (ja) * 2018-01-12 2022-12-12 三星電子株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用組成物、有機エレクトロルミネッセンス素子、及び化合物の製造方法

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US11466017B2 (en) 2011-03-10 2022-10-11 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11
US20160322583A1 (en) * 2013-12-27 2016-11-03 Doosan Corporation Organic electroluminescent device
US11588109B2 (en) 2013-12-27 2023-02-21 Solus Advanced Materials Co., Ltd. Organic electroluminescent device
US10573822B2 (en) * 2013-12-27 2020-02-25 Doosan Corporation Organic electroluminescent device
WO2016013894A3 (fr) * 2014-07-24 2016-08-04 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant un tel composé
KR102238282B1 (ko) 2014-07-24 2021-04-08 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20160012409A (ko) * 2014-07-24 2016-02-03 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
US10230053B2 (en) * 2015-01-30 2019-03-12 Samsung Display Co., Ltd. Organic light-emitting device
US11617290B2 (en) 2015-12-22 2023-03-28 Samsung Display Co., Ltd. Organic light-emitting device
EP3185331A1 (fr) * 2015-12-22 2017-06-28 Samsung Display Co., Ltd. Dispositif électroluminescent organique
US11937500B2 (en) 2015-12-22 2024-03-19 Samsung Display Co., Ltd. Organic light-emitting device
US11696496B2 (en) 2015-12-22 2023-07-04 Samsung Display Co., Ltd. Organic light-emitting device
EP3188277A1 (fr) * 2015-12-29 2017-07-05 Samsung Display Co., Ltd. Dispositif électroluminescent organique
CN112670425A (zh) * 2015-12-29 2021-04-16 三星显示有限公司 有机发光装置
CN106935715A (zh) * 2015-12-29 2017-07-07 三星显示有限公司 有机发光装置
US11678498B2 (en) 2016-04-07 2023-06-13 Samsung Display Co., Ltd. Organic light-emitting device
CN107275496A (zh) * 2016-04-07 2017-10-20 三星显示有限公司 有机发光器件
CN107275496B (zh) * 2016-04-07 2022-04-15 三星显示有限公司 有机发光器件
US10280171B2 (en) 2016-05-31 2019-05-07 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11
US10851110B2 (en) 2016-05-31 2020-12-01 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11
US11840536B2 (en) 2016-05-31 2023-12-12 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of PTPN11
CN111406060B (zh) * 2018-02-02 2023-02-03 株式会社Lg化学 杂环化合物和包含其的有机发光元件
CN111406060A (zh) * 2018-02-02 2020-07-10 株式会社Lg化学 杂环化合物和包含其的有机发光元件
US11997926B2 (en) 2018-02-02 2024-05-28 Lg Chem, Ltd. Heterocyclic compound and organic light emitting element comprising same
US10954243B2 (en) 2018-05-02 2021-03-23 Navire Pharma, Inc. Substituted heterocyclic inhibitors of PTPN11
US11932643B2 (en) 2018-05-02 2024-03-19 Navire Pharma, Inc. Substituted heterocyclic inhibitors of PTPN11
US11104675B2 (en) 2018-08-10 2021-08-31 Navire Pharma, Inc. PTPN11 inhibitors
US11945815B2 (en) 2018-08-10 2024-04-02 Navire Pharma, Inc. PTPN11 inhibitors
EP3643761A1 (fr) 2018-10-25 2020-04-29 Idemitsu Kosan Co., Ltd. Composition, matériau pour dispositif électroluminescent organique, film de composition, dispositif d'électroluminescence organique et dispositif électronique
US11168093B2 (en) 2018-12-21 2021-11-09 Celgene Corporation Thienopyridine inhibitors of RIPK2
WO2022178693A1 (fr) * 2021-02-23 2022-09-01 苏州大学 Procédé de préparation d'un composé benzothiazole à l'aide de n-(2-bromophényl)thioamide sous activation à la lumière visible
CN115043852A (zh) * 2022-07-26 2022-09-13 武汉天马微电子有限公司 一种苯并恶唑衍生物及其电致发光的应用
CN115043852B (zh) * 2022-07-26 2023-12-29 武汉天马微电子有限公司 一种苯并恶唑衍生物及其电致发光的应用

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