WO2018128255A1 - Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage - Google Patents

Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage Download PDF

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Publication number
WO2018128255A1
WO2018128255A1 PCT/KR2017/011928 KR2017011928W WO2018128255A1 WO 2018128255 A1 WO2018128255 A1 WO 2018128255A1 KR 2017011928 W KR2017011928 W KR 2017011928W WO 2018128255 A1 WO2018128255 A1 WO 2018128255A1
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substituted
group
unsubstituted
formula
organic optoelectronic
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PCT/KR2017/011928
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English (en)
Korean (ko)
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류진현
김창우
유은선
장기포
정호국
조영경
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삼성에스디아이 주식회사
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Priority to US16/468,779 priority Critical patent/US11158817B2/en
Priority to CN201780082320.8A priority patent/CN110168048B/zh
Priority claimed from KR1020170140115A external-priority patent/KR102199076B1/ko
Publication of WO2018128255A1 publication Critical patent/WO2018128255A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • 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

  • Compound for organic optoelectronic devices Compound for organic optoelectronic devices.Composition for water organic optoelectronic devices, organic optoelectronic devices and display devices
  • a compound for organic optoelectronic devices a composition for organic optoelectronic devices, an organic optoelectronic device, and a display device.
  • Organic optoelectronic diodes are devices that can switch electrical energy and light energy.
  • Organic optoelectronic devices can be divided into two types according to the principle of operation.
  • One is an optoelectronic device in which an exciton formed by light energy is separated into electrons and holes, and the electrons and holes are transferred to the other electrode to generate electrical energy, and the other is to supply voltage or current to the electrodes. To generate light energy from electrical energy.
  • Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
  • the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material.
  • the organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode.
  • the organic layer may include a light emitting layer and an auxiliary layer, and the auxiliary layer may be, for example, a hole injection layer and a hole transport layer to increase the efficiency and stability of the organic light emitting device. It may include at least one layer selected from an electron blocking layer, an electron transport layer, an electron injection charge and a hole blocking layer.
  • the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic materials included in the organic layer.
  • the organic light emitting diode is applied to a large flat panel display.
  • organic materials that can increase electrochemical stability.
  • One embodiment provides a compound for an organic optoelectronic device capable of implementing high efficiency and long life organic optoelectronic devices.
  • Another embodiment provides an organic optoelectronic device composition comprising the compound for an organic optoelectronic device.
  • Yet another embodiment provides an organic optoelectronic device including the compound.
  • Another embodiment provides a display device including the organic optoelectronic device.
  • a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.
  • ⁇ 1 to ⁇ 3 are each independently ⁇ or CR a ,
  • At least two of Z 1 to Z 3 are N,
  • X is 0 or S
  • L is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
  • Ar is a substituted or unsubstituted C6 to C30 aryl group
  • R a and R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, "Substituted” means that at least one hydrogen is substituted with deuterium, C1 to C20 alkyl group C6 to C30 aryl group, or C2 to C30 heteroaryl group.
  • the compound for a first organic optoelectronic device described above and a second organic optoelectronic device compound including a carbazole moiety represented by Formula 2 below.
  • Y 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
  • a 1 is a substituted or unsubstituted C6 to C30 aryl group, or-a substituted or unsubstituted C2 to C30 heterocyclic group,
  • Each R 16 is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
  • R 13 to R 16 are each independently present or adjacent groups of R 13 to R 16 are connected to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,
  • the "substituted”, at least one hydrogen is hydrogen, C1 to C4 alkyl group,
  • an anode and a cathode facing each other, and at least one layer of the organic layer positioned between the anode and the cathode, the organic layer is a compound for an organic optoelectronic device, or a composition for an organic optoelectronic device It provides an organic optoelectronic device comprising a.
  • a display comprising the organic optoelectronic device Provide the device.
  • FIG. 1 and 2 are cross-sectional views illustrating an organic light emitting diode according to an embodiment.
  • substituted is a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, nitro group, substituted Or unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group.C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, It is substituted with a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group / C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.
  • substituted means that at least one hydrogen of the substituent or compound is deuterium, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group.
  • a "substituted" shall have at least one hydrogen in the substituent or a compound means that the heavy hydrogen, C1 to C20 alkyl groups, C6 to C30 aryl group, or a C2 to C30 heteroaryl group substituted .
  • substituted means that at least one hydrogen of the substituent or compound is deuterium, C1 to C5 alkyl group, C6 to C18 aryl group, pyridinyl group, quinolinyl group, isoquinolinyl group, di Mean substituted by a benzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.
  • substituted means that at least one hydrogen of the substituent or compound is deuterium, C1 to C5 alkyl group, C6 to It means substituted with a C18 aryl group, dibenzofuranyl group or dibenzothiophenyl group.
  • substituted means that at least one hydrogen of the substituent or compound is deuterium, methyl, ethyl, Mean substituted by propaneyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, dibenzofuranyl group or dibenzothiophenyl group.
  • hetero means one to three heteroatoms selected from the group consisting of N, 0, S, P, and Si in one functional group, and the rest are carbon unless otherwise defined.
  • alkyl group means an aliphatic hydrocarbon group.
  • Alkyl groups may be “saturated alkyl groups” that do not contain any double or triple bonds.
  • the alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group.
  • a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, and methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl. sec-butyl and t-butyl.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus. It means a practical skill.
  • an "aryl group” refers to a group of groups having one or more hydrocarbon aromatic moieties.
  • All of the elements of the hydrocarbon aromatic moiety have a P-orbital, and these P-orbitals form a conjugate (conj ugat i on), such as a phenyl group, a naphthyl group, and the like.
  • Two or more hydrocarbon aromatic moieties are linked via sigma bonds, such as biphenyl groups, terphenyl groups, quarterphenyl groups, etc.
  • It may also comprise a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are fused directly or indirectly.
  • a fluorenyl group may be mentioned.
  • Aryl groups include monocyclic, polycyclic or fused ring polycyclic (ie, rings having adjacent pairs of carbon atoms) functional groups.
  • the term "heterocyc lic group” is a higher concept including a heteroaryl group, and N, 0 instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. It means that it contains at least one hetero atom selected from the group consisting of S, P and Si.
  • the heterocyclic group may include one or more heteroatoms for all or each ring.
  • heteroaryl group means containing at least one hetero atom selected from the group consisting of N, 0, S, P and Si in the aryl group.
  • Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused to each other.
  • each ring may include 1 to 3 heteroatoms.
  • the heterocyclic group may include, for example, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like.
  • a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted naphthacenyl group substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group substituted or unsubstituted m-terphenyl group, substituted or unsubstituted 0-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylene group, substituted or or un
  • Substituted or unsubstituted indenyl group substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, Substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazoleyl group, substituted or unsubstituted thiadiazoleyl group, substituted or unsubstituted A substituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or Unsubstituted tri
  • Substituted tc unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted unsubstituted benzoxazinyl group, substituted or unsubstituted Substituted benzthiazinyl group, substituted C unsubstituted acridinyl group, substituted or unsubstituted phenazineyl group, substituted c unsubstituted phenothiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted unsubstituted
  • the dibenzofuranyl group CC may be a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.
  • the hole property refers to a property capable of forming holes by donating electrons when an electric field is applied, and as a light emitting layer of a hole formed at the anode having a conductive property along the HOMO quasi-level. It means the characteristic that facilitates the injection, movement of the holes formed in the light emitting layer to the anode and movement in the light emitting layer.
  • the compound for an organic optoelectronic device according to one embodiment is represented by the following formula (1).
  • Z 1 to Z 3 are each independently N or CR a , At least two of Z 1 to V are N,
  • X is 0 or S
  • L is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
  • Ar is a substituted or unsubstituted C6 to C30 aryl group
  • R a and R 1 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
  • substituted means that at least one hydrogen is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group.
  • the "substituted” may mean that at least one hydrogen is substituted with deuterium, C1 to C20 alkyl group, or C6 to C30 aryl group, more specifically at least one hydrogen is deuterium, C1 To C10 alkyl group, phenyl group, biphenyl group, or naphthyl group. It may mean substituted.
  • the compound for an organic optoelectronic device has a T core containing an N-containing six-membered ring, which includes a substituent directly connected without a linking group at position 2 of dibenzofuran or dibenzothiophene, thereby effectively expanding the LUM0 energy band and forming a molecular structure.
  • the planarity of the structure may be increased, and thus the structure may easily receive electrons when an electric field is applied, thereby lowering the driving voltage of the organic optoelectronic device to which the compound for an organic optoelectronic device is applied.
  • the expansion of LUM0 and the fusion of rings increase the stability of the electrons of the ⁇ core, which is effective in improving device life.
  • the glass transition degree (Tg) of the compound is higher than that of the dialkyl fluorene-substituted structure, thereby increasing stability of the compound during the process and preventing deterioration when applied to the device.
  • the glass transition temperature (Tg) may be related to the thermal stability of the compound and the device to which it is applied. That is, the compound for an organic optoelectronic device having a high glass transition temperature (Tg), when applied to the organic light emitting device in the form of a thin film, is a subsequent process, such as after deposition of the compound for the organic optoelectronic device In the encapsulat ion process, it is prevented from being degraded by temperature, thereby ensuring the life characteristics of the organic compound and the device.
  • the diphenyl fluorene is substituted at the 4 position, it is possible to secure a much lower deposition temperature at the same molecular weight than the structure in which fluorene is substituted at another position, thereby preventing deterioration during high temperature storage or deposition process. . Accordingly, the driving voltage, efficiency, and lifespan characteristics of the organic optoelectronic device to which the compound for organic optoelectronic devices is applied may be improved.
  • Formula 1 may be represented by any one of the following Formula 1A, Formula 1B and Formula 1C, depending on the position of substitution of diphenyl fluorene.
  • Formula 1 may be represented by any one of the following Formula 1-1, Formula 1- ⁇ and formula im depending on the number and position of N included in Z 1 to Z 3 .
  • Formula 1-1 Formula 1-I, and Formula 1-m, X, L, Ar, and R to R 10 are the same as described above, and R al to R a3 are the same as the definitions of R a .
  • L of Chemical Formula 1 may be a single bond. More specifically, of Chemical Formula 1A, Xing-group Chemical Formula 1B, Chemical Formula 1C, Chemical Formula, Chemical Formula ⁇ - ⁇ and Chemical Formula l-m. [May be a single combination.
  • Chemical Formula 1 is preferably a structure represented by Chemical Formula 1C or Chemical Formula 1-1, and most preferably, a structure represented by Chemical Formula 1C.
  • Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted flu Orenyl group.
  • Ar may be a phenyl group, a biphenyl group, or a terphenyl group.
  • the biphenyl group may be a met a—biphenyl group or a para-biphenyl group
  • the terphenyl group may be a meta-terphenyl group, a terphenyl group connected to met a in an i so form.
  • R 1 to R 10 are each independently hydrogen, deuterium, methyl group, ethyl group, n-propyl group, i so-propyl group, It may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, specifically, R 1 to R 10 may be each independently hydrogen, methyl group, ethyl group, or phenyl group, the most specific embodiment of the present invention In an example, R 1 to R 10 may be hydrogen or a phenyl group, and more specifically, R 1 to R 10 may be all hydrogen.
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be selected from, for example, the compounds listed in Group 1, but is not limited thereto.
  • the above-mentioned first compound for organic optoelectronic devices may be applied to an organic optoelectronic device, or may be applied to an organic optoelectronic device alone or in combination with other compounds for organic optoelectronic devices.
  • the compound for an organic optoelectronic device described above is used together with another compound for an organic optoelectronic device, it may be applied in the form of a composition.
  • an example of the composition for organic optoelectronic devices including the above-described first compound for organic optoelectronic devices will be described.
  • Composition for an organic optoelectronic device is a compound for a first organic optoelectronic device described above; And a second organic optoelectronic device compound including a carbazole moiety represented by Formula 2 below.
  • Y 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
  • a 1 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
  • Rll to Rl 6 are each independently hydrogen, deuterium, substituted or unsubstituted
  • R 13 to R 16 are each independently present or adjacent groups of R 13 to R 16 are connected to form a substituted or unsubstituted aliphatic aromatic or heteroaromatic monocyclic or polycyclic ring.
  • Substituted means that at least one hydrogen is deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroa ; Mean substituted by a aryl group. In a specific embodiment of the present invention, the "substituted”. It means that at least one hydrogen is substituted with deuterium, phenyl group, or tho-biphenyl group, met a-biphenyl group, para-biphenyl group, terphenyl group, naphthyl group, dibenzofuranyl group or dibenzothiophenyl group.
  • Formula 2 is represented by the following Formula 2A.
  • a composition for an organic optoelectronic device which is one selected from a combination of Formulas 2B-1 and 2B-2:
  • Y 1 to Y 3 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
  • a 1 to A 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
  • R 11 to R 13 , and R 17 to R 21 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 hetero Ring groups, or a combination thereof.
  • ni 0.
  • Formula 2 may be represented by the following Formula 2A or Formula 2C.
  • Y 2 and Y 3 are the same as the definition of Y 1 described above, A 2 and A 3 are the same as the definition of A 1 described above, R 17 to R 21 are the same as the definition of R 11 to R 16 described above, m is one of the integers of 0-2.
  • Y 1 to Y 3 of Formula 2A, Formula 2B-1, Formula 2B-2, and Formula 2C each independently represent a single bond, or a substituted or unsubstituted C6 to C18 arylene. It may be a flag. Specifically, it may be a single bond, met a-phenylene group, or para-phenylene group.
  • a 1 to A 3 of Formula 2A, Formula 2B-1, Formula 2B-2, and Formula 2C are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group.
  • Substituted or unsubstituted Terphenyl group substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or Unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted fluorenyl group, or a combination thereof.
  • substituted or unsubstituted phenyl group substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzo It may be a thiophenyl group, or a substituted or unsubstituted dibenzofuranyl group.
  • R 11 to R 13 , and R 17 to R 21 are each independently hydrogen, deuterium, or substituted or unsubstituted. It may be a C6 to C12 aryl group. Specifically, it may be hydrogen or a phenyl group.
  • the binding position of carbazoles in the core of biscarbazole is more preferably 2, 3-bond, 3, 3-bond or 2, 2-bond, and 3 : 3. Bonding is more preferred.
  • Formula 2A is one of the structures listed in Group I below, and * SE and * —Y 2 — A 2 may be one of the substituents listed in Group II below.
  • the compound for the organic optoelectronic device 2 is represented by Formula 2 may be selected from, for example, the compounds listed in Group 2.
  • the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device described above may prepare various compositions by various combinations.
  • composition according to an embodiment of the present invention may include a compound represented by Formula 1C as a first host, and may include a compound represented by Formula 2A or 2C as a second host.
  • Z 1 to Z 3 of Formula 1C may be all N.
  • the formula 2A can be a structure represented by formula C-8 or C-17 of the group I, ⁇ - ⁇ 1 and -Y 2 -A 2 are to the * groups ⁇ B-1, B-2 , And B-3.
  • the second compound for an organic optoelectronic device may improve the light emission efficiency by increasing the reliability it is 1, using the light-emitting layer, with a compound for an organic optoelectronic device to increase the mobility of charge and lifetime characteristics.
  • the mobility of the charge may be controlled by controlling the ratio of the second organic optoelectronic device compound and the first organic optoelectronic device compound.
  • the combination ratio thereof may vary depending on the type of dopant used or the propensity of the dopant, or 0LED when the composition of the present invention is used in an electron transport layer or an electron transport auxiliary layer. Used in the device
  • the compound and the combination ratio of the composition of the present invention may vary. For example, it may be included in a weight ratio of about 1: 9 to 9: 1, and specifically 1: 9 to 8: 2, 1: 9 to 7: 3, 1: 9 to 6: 4, 1: 9 to 5: 5 It may be included in the range, 2: 8 to 8: 2, 2: 8 to 7: 3, 2: 8 to
  • composition of the present invention when used as a host.
  • the second compound for an organic optoelectronic device Sean 1 compound for an organic optoelectronic device: 9 to 5: 5, 2: 8 to 5: 5, 3: may be included in a weight ratio range of 5: 7 to 5.
  • the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device are 2: 8 to 8: 2,
  • the mixing ratio of the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be 3: 7 to 5: 5, for example, 3: 7 or 5: 5.
  • the composition may further include at least one organic compound in addition to the above-mentioned compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device.
  • the compound for an organic optoelectronic device may further include a dopant.
  • the dopant may be a red, green or blue dopant.
  • the dopant is a substance that is lightly mixed to cause light emission. Materials such as metal complexes that emit light by multiple excitation that excite triplet state subphases can be used.
  • the dopant may be, for example, an inorganic, organic, or inorganic compound, and may be included in one kind or two or more kinds.
  • An example of the dopant may be a phosphorescent dopant, and an example of the phosphorescent dopant may be Ir, Pt, 0s, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or And organometallic compounds containing a combination of these.
  • the phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.
  • M is a metal
  • L and X are the same or different from each other, and are ligands that form a complex with M.
  • M may be, for example, Ir, Pt, 0s, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, wherein L and X are, for example, Tate ligand.
  • an organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic insect is the compound for an organic optoelectronic device described above, or an organic optoelectronic device. It may include a composition for the device.
  • the organic layer may include a light emitting layer
  • the light emitting layer may include a compound for an organic optoelectronic device or a composition for an organic optoelectronic device.
  • the compound for an organic optoelectronic device, or a composition for an organic optoelectronic device may be included as a host of the light emitting layer, for example, a green host.
  • the organic layer may include a light emitting layer and at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and a hole blocking layer, and the auxiliary layer may be a compound for the organic optoelectronic device. , Or organic It may include a composition for an optoelectronic device.
  • the auxiliary layer further comprises an electron transport auxiliary layer adjacent to the light emitting layer J1,
  • the electron transport auxiliary layer is the compound for the organic optoelectronic device. Or a composition for an organic optoelectronic device.
  • the compound for an organic optoelectronic device when included in the electron transport layer or the electron transport auxiliary layer, the compound for an organic optoelectronic device may be represented by Formula 1C or Formula 1-1.
  • the organic optoelectronic device is not particularly limited as long as the device can switch electrical energy and light energy. Examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.
  • FIG. 1 and 2 are cross-sectional views illustrating an organic light emitting diode according to an embodiment.
  • an organic optoelectronic device 100 includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110. Include.
  • the anode 120 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the anode 120 is, for example, a metal such as nickel, platinum, vanadium, cream, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, sulphite tin ⁇ 0), and sulphite zinc oxide (IZ0); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3l methylthiophene), poly (3,4 '(ethylene-1,2'dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, and the like. It is not limited.
  • the cathode 110 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the cathode 110 is, for example, magnesium, calcium, sodium, potassium, titanium. Indium, yttrium, lithium, gadolinium, aluminum, silver. Tin, lead, Metals such as cesium, barium, or alloys thereof; Multilayer structure materials such as LiF / Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
  • the organic layer 105 includes an emission layer 130 containing the compound for an organic optoelectronic device described above.
  • . 2 is a cross-sectional view illustrating an organic light emitting device according to another embodiment.
  • the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130.
  • the hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
  • the hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.
  • the organic layer 105 of FIG. 1 or 2 is an electron injection insect. It may further include an electron transport layer, an electron transport auxiliary layer, a hole transport layer, a hole transport auxiliary layer, a hole injection layer or a combination thereof.
  • the compound for an organic optoelectronic device of the present invention may be included in these organic layers.
  • the organic light emitting device (100.200) is formed on the substrate by an anode or a cathode, and then evaporation.
  • the organic layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode or an anode thereon.
  • the organic light emitting diode described above may be applied to an organic light emitting display device.
  • Comparative Compound 1 was obtained in the same manner with reference to paragraph 830 of Korean Patent Registration Publication No. KR1542714.
  • the glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500A was washed with distilled water ultrasonic waves. After the washing using distilled water was isopropyl alkoeul. Ultrasonic washing with a solvent such as acetone, methanol, and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 10 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • Compound A was vacuum deposited on the IT0 substrate using the prepared IT0 transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then compound C was deposited to a thickness of 50 A on the injection layer. Depositing a thickness of 1020 A to form a hole transport layer.
  • Compound A-1 of Synthesis Example 1 was used as a host on the hole transport layer, and dostrotris ((2- [1,1'-biphenyl] -3-yl) pyridine) iridium ( ⁇ or less GDI) was added to 10%. Doped to form a light emitting layer of 400A thickness by vacuum deposition. Subsequently, compound D and Liq are simultaneously vacuum deposited at a ratio of 1: 1 on the emission layer to form an electron transport layer having a thickness of 300 A, and Liq 15A and Al 1200A are sequentially vacuum deposited on the electron transport layer to form a cathode. The device was produced.
  • the organic light emitting device has a structure having five layers of organic thin film worms, specifically as follows.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A-1 and Compound E-99 were deposited together at a weight ratio of 30:70 to form a light emitting layer.
  • the configuration of the light emitting layer of the organic light emitting device is as follows.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A-1 and Compound F-55 were deposited together at a weight ratio of 30:70 to form a light emitting layer.
  • the configuration of the light emitting layer of the organic light emitting device is as follows.
  • An organic light emitting device was manufactured in the same manner as in Examples 1 to 3, except that Compound A-13 was used instead of Compound A-1.
  • the configuration of the light emitting layer of the organic light emitting device is as follows.
  • Example 7 electron transport layer
  • An organic light emitting diode was manufactured according to the same method as Example 7 using Compound A-13 instead of Compound A-1 for the electron transport layer. Comparative Example 2
  • An organic light emitting diode was manufactured according to the same method as Example 7 using Comparative Compound 1 instead of Compound A-1 for the electron transport layer. Evaluation 1 (phosphorescent green host)
  • the current value flowing through the unit device was measured using a current-voltmeter (Kei thley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
  • the luminance at that time was measured using a luminance meter (Minol ta Cs_1000A) while increasing the voltage from 0V to 10V to obtain a result.
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2 ) was calculated using the brightness, current density and voltage measured from (1) and (2).
  • the devices of Examples 1 to 3 and Comparative Example 1 were emitted at an initial luminance (c (l / m 2 ) of 18000 cd / m 2 , and the luminance was decreased over time. The time point when the brightness was reduced to 97% of the brightness was measured as the life of T97.
  • the organic light emitting device according to Examples 1 to 6 is a comparative example
  • the specific measuring method is the same as in Evaluation 1, the life measuring method is as follows, and the results are shown in Table 2.
  • the devices of Examples 7, 8 and Comparative Example 2 were emitted with an initial luminance (cd / m 2 ) of 750 cd / m 2 and then over time. According to the decrease in luminance, the time point when the luminance was reduced to 97% of the initial luminance was measured as the life of T97.
  • Example 7 Compound A-1 3.76 114% 132%
  • Example 8 Compound A-13 3.43 120% 151 Comparative Example 2 Comparative Compound 1 4.25 100% 100% Referring to Table 2, the organic according to Example 7 and Example 8 was obtained. The light emitting device compared to the organic light emitting device according to Comparative Example 2, it can be seen that the driving voltage, luminous efficiency and life characteristics are all broken at the same time.

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

Abstract

L'invention concerne un composé exprimé par la formule 1 pour un élément optoélectronique organique, une composition pour un élément optoélectronique organique, un élément optoélectronique organique la comprenant et un dispositif d'affichage. Les détails de la formule chimique (1) sont tels que définis dans la description.
PCT/KR2017/011928 2017-01-05 2017-10-26 Composé pour élément optoélectronique organique, composition pour élément optoélectronique organique, élément optoélectronique organique et dispositif d'affichage WO2018128255A1 (fr)

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US16/468,779 US11158817B2 (en) 2017-01-05 2017-10-26 Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
CN201780082320.8A CN110168048B (zh) 2017-01-05 2017-10-26 有机光电装置、用于其的化合物及组成物以及显示装置

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KR10-2017-0001941 2017-01-05
KR10-2017-0140115 2017-10-26
KR1020170140115A KR102199076B1 (ko) 2017-01-05 2017-10-26 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11084806B2 (en) 2016-07-12 2021-08-10 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
US11158817B2 (en) 2017-01-05 2021-10-26 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
US11264574B2 (en) 2016-07-29 2022-03-01 Samsung Sdi Co., Ltd. Composition for organic optoelectronic element, organic optoelectronic element, and display device
WO2022163735A1 (fr) 2021-01-29 2022-08-04 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
US11678572B2 (en) 2016-06-29 2023-06-13 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus
US11706975B2 (en) 2016-06-29 2023-07-18 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150042335A (ko) * 2013-10-10 2015-04-21 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN105153130A (zh) * 2015-08-03 2015-12-16 上海道亦化工科技有限公司 三嗪类衍生物电子传输化合物及其有机电致发光器件
KR20160006633A (ko) * 2014-07-09 2016-01-19 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
WO2016172414A1 (fr) * 2015-04-22 2016-10-27 Rohm And Haas Electronic Materials Llc Couche de transport d'électrons et film présentant une stabilité thermique améliorée
US20170025618A1 (en) * 2015-04-06 2017-01-26 Universal Display Corporation Organic Electroluminescent Materials and Devices
WO2017016630A1 (fr) * 2015-07-30 2017-02-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR20170116992A (ko) * 2016-04-12 2017-10-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150042335A (ko) * 2013-10-10 2015-04-21 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20160006633A (ko) * 2014-07-09 2016-01-19 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 소자
US20170025618A1 (en) * 2015-04-06 2017-01-26 Universal Display Corporation Organic Electroluminescent Materials and Devices
WO2016172414A1 (fr) * 2015-04-22 2016-10-27 Rohm And Haas Electronic Materials Llc Couche de transport d'électrons et film présentant une stabilité thermique améliorée
WO2017016630A1 (fr) * 2015-07-30 2017-02-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
CN105153130A (zh) * 2015-08-03 2015-12-16 上海道亦化工科技有限公司 三嗪类衍生物电子传输化合物及其有机电致发光器件
KR20170116992A (ko) * 2016-04-12 2017-10-20 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11678572B2 (en) 2016-06-29 2023-06-13 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus
US11706975B2 (en) 2016-06-29 2023-07-18 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus
US11084806B2 (en) 2016-07-12 2021-08-10 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
US11264574B2 (en) 2016-07-29 2022-03-01 Samsung Sdi Co., Ltd. Composition for organic optoelectronic element, organic optoelectronic element, and display device
US11158817B2 (en) 2017-01-05 2021-10-26 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device
WO2022163735A1 (fr) 2021-01-29 2022-08-04 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
KR20230138466A (ko) 2021-01-29 2023-10-05 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광소자 및 전자 기기

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