WO2014021572A1 - Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique contenant ce composé - Google Patents

Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique contenant ce composé Download PDF

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WO2014021572A1
WO2014021572A1 PCT/KR2013/006464 KR2013006464W WO2014021572A1 WO 2014021572 A1 WO2014021572 A1 WO 2014021572A1 KR 2013006464 W KR2013006464 W KR 2013006464W WO 2014021572 A1 WO2014021572 A1 WO 2014021572A1
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substituted
unsubstituted
group
fused
heterocycloalkyl
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PCT/KR2013/006464
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English (en)
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Ju-Sik Kang
Jeong Ho Park
Suk Woon JUN
Yong-Jun Shin
Yu-Mi Chang
Nam-Choul Yang
Jae-Kyun Park
Song Lee
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Sk Chemicals Co., Ltd.
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Priority claimed from KR1020130079852A external-priority patent/KR20140018789A/ko
Application filed by Sk Chemicals Co., Ltd. filed Critical Sk Chemicals Co., Ltd.
Publication of WO2014021572A1 publication Critical patent/WO2014021572A1/fr

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Definitions

  • the present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device including the same, and more particularly, to a compound for an organic electroluminescent device, having high light emission efficiency and low driving, and to an organic electroluminescent device including the same.
  • Organic electroluminescent (EL) devices have a simpler structure, various processing advantages, higher brightness, superior viewing angle properties, quicker response rate, and a lower driving voltage compared to other flat panel displays such as liquid crystal displays (LCDs), plasma display panels (PDPs), field emission displays (FEDs), etc., and are thus being thoroughly developed so as to be utilized as light sources of flat panel displays such as wall-mountable TVs, etc. or backlight units of the displays, illuminators, advertisement boards and so on.
  • LCDs liquid crystal displays
  • PDPs plasma display panels
  • FEDs field emission displays
  • Hole transport materials for use in organic EL devices which have been known to date, are problematic because thin films formed therefrom using vacuum deposition are thermally and electrically unstable, and thus may rapidly crystallize due to heat generated upon device driving and also the film materials may change, undesirably deteriorating the light emission efficiency of the devices. Further, non-emission parts referred to as dark spots may increasingly occur, and the voltage may increase upon constant-current driving, undesirably damaging the devices.
  • organic EL devices using a phosphorescent light emitting material do not confine a triplet exciton produced in the light emitting material of a light emitting layer due to low triplet energy, undesirably lowering the light emission efficiency of the devices.
  • an object of the present invention is to provide a compound for an organic EL device, which may have high thermal stability, high triplet energy and hole transport capability.
  • Another object of the present invention is to provide an organic EL device, which includes the compound as above and is thus improved in thermal stability and light emission efficiency, and in which the above compound is used as a hole transport layer material, thereby confining a triplet exciton of a phosphorescent light emitting material, ultimately improving efficiency of the organic EL device.
  • an aspect of the present invention provides a compound for an organic EL device which represented by any one selected from among Chemical Formulas 1 to 6 below.
  • R 1 to R 2 are identical to or different from each other, and R 1 to R 2 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 1 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused
  • n 0 or 1
  • n 0 or 1
  • R 3 to R 14 are identical to or different from each other, and R 3 to R 14 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or , or at least one of R 3 to R 14 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substitute
  • Ar 1 and Ar 2 are identical to or different from each other, and Ar 1 and Ar 2 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar 1 and Ar 2 , respectively, are linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween, or at least one of Ar 1 and Ar 2 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or unsubstituted fused C1
  • R 15 to R 17 are identical to or different from each other, and R 15 to R 17 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • a 1 and A 2 are identical to or different from each other, and A 1 and A 2 are each independently a valence bond or ,
  • R 18 and R 19 are identical to or different from each other, and R 18 and R 19 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group,
  • a1 is 0 or 1
  • a2 is 0 or 1.
  • the compound for an organic EL device is represented by any one selected from among Chemical Formulas 7 to 9 below.
  • R 1 and R 2 are identical to or different from each other, and R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 1 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused
  • n 0 or 1
  • n 0 or 1
  • R 3 to R 14 are identical to or different from each other, and R 3 to R 14 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or , or at least one of R 3 to R 14 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substitute
  • Ar 1 and Ar 2 are identical to or different from each other, and Ar 1 and Ar 2 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar 1 and Ar 2 , respectively, are linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween, or at least one of Ar 1 and Ar 2 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or unsubstituted fused C1
  • R 15 to R 17 are identical to or different from each other, and R 15 to R 17 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • a 1 is a valence bond or ,
  • R 18 and R 19 are identical to or different from each other, and R 18 and R 19 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group,
  • a1 is 0 or 1.
  • the compound for an organic EL device is represented by Chemical Formula 10 below.
  • R 1 and R 2 are identical to or different from each other, and R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or R 1 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituteduted
  • n 0 or 1
  • n 0 or 1
  • R 3 to R 14 are identical to or different from each other, and R 3 to R 14 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or , or at least one of R 3 to R 14 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group, a substituted or unsubstituted fused C6 to C30 aryl group, or a substitute
  • Ar 1 and Ar 2 are identical to or different from each other, and Ar 1 and Ar 2 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar 1 and Ar 2 , respectively, are linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween, or at least one of Ar 1 and Ar 2 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or unsubstituted fused C
  • R 15 to R 17 are identical to or different from each other, and R 15 to R 17 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
  • R 1 and R 2 are identical to or different from each other, and R 1 and R 2 are each independently a hydrogen atom, , , , , a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or R 1 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C3 to C30 cycloalkyl group, a substituted or unsubstituted fused C1 to C30 heterocycloalkyl group or a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
  • Y 1 and Y 2 are identical to or different from each other, and Y 1 and Y 2 are each independently an oxygen atom, a sulfur atom, , or ,
  • Ar 7 is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • R 29 and R 30 are identical to or different from each other, and R 29 and R 30 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • Ar 3 to Ar 6 are identical to or different from each other, and Ar 3 to Ar 6 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or Ar 3 and Ar 4 , and Ar 5 and Ar 6 , respectively, are linked to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, together with a nitrogen atom therebetween, or at least one of Ar 3 to Ar 6 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or un
  • R 20 to R 28 are identical to or different from each other, and R 20 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group,
  • q 0 or 1.
  • Ar 3 to Ar 6 are identical to or different from each other, and Ar 3 to Ar 6 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of Ar 3 to Ar 6 is further coupled with a carbon atom on the ⁇ position of a nitrogen atom linked therewith to form a substituted or unsubstituted C1 to C30 heterocycloalkyl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
  • Ar 1 and Ar 2 are identical to or different from each other, and Ar 1 and Ar 2 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group.
  • Examples of the substituted or unsubstituted C6 to C30 aryl group may include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthalenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted perylenyl group.
  • Examples of the substituted or unsubstituted C1 to C30 heteroaryl group may include a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo[1,2-a]pyridinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazin
  • a substituted or unsubstituted pyridinyl group a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted imidazo[1,2-a]pyridinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl
  • the compound for an organic EL device may be any one selected from among Compounds 1 to 48 represented by the following chemical formulas.
  • an organic electroluminescent (EL) device including the compound for an organic EL device according to the present invention may be provided.
  • an organic EL device may include a first electrode, a second electrode, and a single organic layer or a plurality of organic layers between the first electrode and the second electrode, and one or more organic layers selected from among the single organic layer or the plurality of organic layers may include the compound for an organic EL device according to the present invention.
  • the single organic layer or the plurality of organic layers may include a light emitting layer.
  • the plurality of organic layers may include a light emitting layer, and the plurality of organic layers may further include one or more selected from among an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer and a hole injection layer.
  • the light emitting layer may include a host and a dopant.
  • a terphenyl derivative is prepared, and substituted by diarylamine.
  • This compound is contained in the organic layer of an organic EL device, and the use of the compounds as a phosphorescent light emitting material in the organic EL device enable to increase the triplet energy, thus improving thermal stability and light emission efficiency.
  • FIG. 1 is a cross-sectional view illustrating an organic EL device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view illustrating an organic EL device according to another embodiment of the present invention.
  • the present invention may be variously modified, and may have a variety of embodiments, and is intended to illustrate specific embodiments. However, the following description does not limit the present invention to specific embodiments, and should be understood to include all variations, equivalents or substitutions within the spirit and scope of the present invention. Furthermore, in the description of the present invention, when it is determined that the detailed description of the related art would obscure the gist of the present invention, the description thereof will be omitted.
  • first a first component
  • second a second component
  • first component a first component
  • any one component when any one component is mentioned to be “formed” or “stacked” on another component, it may be directly attached to the entire surface or one surface of another component, or a further component may be additionally interposed therebetween.
  • the singular expression includes a plural expression.
  • the terms “include” and “have” are used to designate the presence of features, numbers, steps, operations, components, parts or combinations thereof described in the specification, not intending to exclude the presence or additional possibility of one or more different features, numbers, steps, operations, components, parts or combinations thereof are not excluded.
  • valence bond means a single bond, a double bond or a triple bond.
  • substituted means that at least one hydrogen on a substituent or a compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C30 silyl group, a C1 to C30 alkyl group, a C1 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C1 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C1 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group.
  • two adjacent substituents may be fused to form a ring.
  • hetero means a functional group containing 1 ⁇ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon.
  • the term “combination thereof” means that two or more substituents are coupled with each other by a linker or two or more substituents are condensed to each other.
  • hydrogen means hydrogen, deuterium or tritium.
  • alkyl group means an aliphatic hydrocarbon group.
  • the alkyl group may be a “saturated alkyl group” without any double bond or triple bond.
  • the alkyl group may be an “unsaturated alkyl group” with at least one double bond or triple bond.
  • alkenylene group means a functional group having at least one carbon-carbon double bond between at least two carbon atoms
  • alkynylene group means a functional group having at least one carbon-carbon triple bond between at least two carbon atoms.
  • the alkyl group may be branched, linear or cyclic, regardless of whether it is saturated or unsaturated.
  • the alkyl group may be a C1 to C30 alkyl group, preferably a C1 to C20 alkyl, more preferably a C1 to C10 alkyl group, and much more preferably a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group indicates an alkyl chain containing 1 ⁇ 4 carbon atoms, particularly an alkyl chain which is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, an ethenyl group, a propenyl group, a butenyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc.
  • the “amine group” includes an arylamine group, an alkylamine group, an arylalkylamine group, or an alkylarylamine group.
  • cycloalkyl group refers to a monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) functional group.
  • heterocycloalkyl group means a cycloalkyl group containing 1 ⁇ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon. In the case where the heterocycloalkyl group is a fused ring, each ring may contain 1 ⁇ 4 heteroatoms.
  • aromatic group means a cyclic functional group where all ring atoms have p-orbitals, and these p-orbitals form conjugation. Specific examples thereof include an aryl group and a heteroaryl group.
  • aryl group refers to a monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) functional group.
  • heteroaryl group means an aryl group containing 1 ⁇ 4 heteroatoms selected from the group consisting of N, O, S and P, the remainder being carbon. In the case where the heteroalkyl group is a fused ring, each ring may contain 1 ⁇ 4 heteroatoms.
  • the number of ring atoms is the sum of the number of carbons and the number of non-carbon atoms.
  • alkyl and aryl are used in combination as in “alkylaryl group” or “arylalkyl group,” “alkyl” and “aryl” respectively have the meanings as above.
  • arylalkyl group means an aryl substituted alkyl radical such as benzyl, and is incorporated in the alkyl group.
  • alkylaryl group means an alkyl substituted aryl radical, and is incorporated in the aryl group.
  • carbon atom at the ⁇ position of any one atom refers to a carbon atom adjacent to another atom linked with the one atom.
  • carbon atom at the ⁇ position of a nitrogen atom is a carbon atom indicated by the arrow in the following chemical formula.
  • an organic EL device 1 including the compound for an organic EL device according to the present invention may be provided.
  • an organic EL device includes a first electrode 110, a second electrode 150, and a single organic layer or a plurality of organic layers 130 between the first electrode and the second electrode, and one or more organic layers selected from among the single organic layer or the plurality of organic layers 130 may include the compound for an organic EL device according to the present invention.
  • the single organic layer or the plurality of organic layers 130 may include a light emitting layer 134.
  • the plurality of organic layers 130 include a light emitting layer 134, and the plurality of organic layers 130 may further include one or more selected from among an electron injection layer 131, an electron transport layer 132, a hole blocking layer 133, an electron blocking layer 135, a hole transport layer 136 and a hole injection layer 137.
  • the light emitting layer 134 may include a host and a dopant.
  • the organic EL device is preferably supported by a transparent substrate.
  • the material for the transparent substrate is not particularly limited so long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof may include glass, a transparent plastic film, etc.
  • the anode material of the organic EL device according to the present invention may include a metal, an alloy, an electrically conductive compound or a mixture thereof, having a work function of 4 eV or more. Specific examples thereof may include Au metal or a transparent conductive material such as CuI, ITO (indium tin oxide), SnO 2 and ZnO.
  • the thickness of the anode film is preferably set to 10 ⁇ 200 nm.
  • the cathode material of the organic EL device according to the present invention may include a metal, an alloy, an electrically conductive compound or a mixture thereof, having a work function of less than 4 eV. Specific examples thereof may include Na, a Na-K alloy, calcium, magnesium, lithium, a lithium alloy, indium, aluminum, a magnesium alloy, or an aluminum alloy. In addition, aluminum/AlO 2 , aluminum/lithium, magnesium/silver or magnesium/indium may be used. The thickness of the cathode film is preferably set to 10 ⁇ 200 nm.
  • one or more electrodes preferably have a light transmittance of 10% or more.
  • the sheet resistance of the electrodes is preferably hundreds of ⁇ /mm or less.
  • the thickness of the electrodes falls in the range of 10 nm ⁇ 1 ⁇ m, and preferably 10 ⁇ 400 nm.
  • Such electrodes may be manufactured in the form of a thin film using the above electrode material via vapor deposition such as chemical vapor deposition (CVD), physical vapor deposition (PVD) or the like, or sputtering.
  • CVD chemical vapor deposition
  • PVD physical vapor deposition
  • a hole transport material, a hole injection material, a light emitting layer material, a host material for a light emitting layer, an electron transport material, and an electron injection material may be used alone in each organic layer, or may be used in selective combination with the compound for an organic EL device according to the present invention.
  • Examples of the hole transport material may include porphyrin compound derivatives including N,N-dicarbazolyl-3,5-benzene (mCP), poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl (TPD), N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N,N,N'N'-tetraphenyl-4,4'-diaminobiphenyl, 1,10,15,20-te
  • Examples of the electron transport material may include diphenylphosphine oxide-4-(triphenylsilyl)phenyl (TSPO1), Alq 3 , 2,5-diaryl sylol derivatives (PyPySPyPy), perfluorinated compounds (PF-6P), octasubstituted cyclooctatetraene compounds (COTs), etc.
  • TSPO1 diphenylphosphine oxide-4-(triphenylsilyl)phenyl
  • Alq 3 2,5-diaryl sylol derivatives
  • PF-6P perfluorinated compounds
  • COTs octasubstituted cyclooctatetraene compounds
  • an electron injection layer, an electron transport layer, a hole transport layer and a hole injection layer may be provided in the form of a single layer containing one or more kinds of the above compound, or may be provided in the form of a plurality of stacked layers containing different kinds of compounds.
  • the light emitting material may include, for example, photoluminescent fluorescent materials, fluorescent brighteners, laser dyes, organic scintillators and fluorescence analysis reagents.
  • specific examples thereof include carbazole-based compounds, phosphine oxide-based compounds, carbazole-based phosphine oxide compounds, polyaromatic compounds including bis((3,5-difluoro-4-cyanophenyl)pyridine)iridium picolinate (FCNIrpic), tris(8-hydroxyquinoline) aluminum (Alq 3 ), anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds including quaterphenyl, scintillators for liquid scintillation including 1,4-bis(2-methylstyryl)benzene, 1,4-bis(4-methylstyryl)benzene, 1,4-bis(4-methyl-5-phenyl-2-
  • Each layer of the organic EL device according to the present invention may be provided in the form of a thin film using a known process such as vacuum deposition, spin coating or casting, or may be manufactured using each layer material.
  • the thickness of each layer is not particularly limited, but may be appropriately set depending on the material properties , and may be typically determined in the range of 2 ⁇ 5,000 nm.
  • the compound for an organic EL device according to the present invention may be subjected to vacuum deposition, a thin film formation process is simple and a uniform thin film which does not substantially have pin holes may be easily obtained.
  • a glass substrate coated with an ITO thin film having a thickness of 100 nm was ultrasonically washed with an isopropyl alcohol solvent, dried, placed in a plasma cleaning system so that the substrate was cleaned using oxygen plasma for 5 min, and then transferred into a vacuum deposition system.
  • the ITO transparent electrode thus prepared was used as an anode, and DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolylamino)-phenyl]-biphenyl-4,4'-diamine] was vacuum deposited on the ITO substrate, thus forming a hole injection layer having a thickness of 55 nm.
  • NPB N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine
  • NPB N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine
  • a second hole transport layer was formed to a thickness of 10 nm using Compound 1 on the first hole transport layer.
  • CBP 4,4-N,N-dicarbazolebiphenyl
  • 6 vol% of Ir(PPy) 3 tris(2-phenylpyridine)iridium] as a dopant were vacuum deposited to a thickness of 25 nm on the second hole transport layer, thus forming a light emitting layer.
  • an electron transport layer was formed to a thickness of 30 nm using Bphen [4,7-diphenyl-1,10-phenanthroline] on the light emitting layer.
  • 2 nm thick Liq [lithium quinolate] and 100 nm thick Al were sequentially vacuum deposited on the electron transport layer to form a cathode, thereby manufacturing an organic EL device.
  • Comparative Device Example 1 Manufacture of organic EL device including NPB as second hole transport layer
  • the brightness was measured using a brightness meter (Minolta CS-2000), and the measured brightness value was divided by the current value, thus obtaining brightness efficiency.
  • the color coordinates were measured using a brightness meter (Minolta CS-2000).
  • a terphenyl derivative is prepared, and substituted by diarylamine.
  • This compound is contained in the organic layer of an organic EL device, and the use of the compounds as a phosphorescent light emitting material in the organic EL device enable to increase the triplet energy, thus improving thermal stability and light emission efficiency.

Abstract

Cette invention concerne un composé pour dispositif électroluminescent organique et un dispositif électroluminescent organique contenant ce composé. Ce composé pour dispositif électroluminescent organique présente une meilleure stabilité thermique et une meilleure efficacité lumineuse. Lorsque le composé selon l'invention est utilisé comme matière pour couche de transport de trous, l'énergie du triplet de la matière phosphorescente émettrice de lumière augmente, ce qui augmente l'efficacité du dispositif électroluminescent organique.
PCT/KR2013/006464 2012-07-31 2013-07-19 Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique contenant ce composé WO2014021572A1 (fr)

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WO2015099485A1 (fr) * 2013-12-26 2015-07-02 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
CN105829279B (zh) * 2013-12-26 2018-06-08 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含其的有机电致发光装置
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EP2924753A1 (fr) * 2014-03-25 2015-09-30 Novaled GmbH Dispositifs émettant de la lumière polychromatique et matrice de transport de trou polyvalent pour ceux-ci
WO2015144633A1 (fr) * 2014-03-25 2015-10-01 Novaled Gmbh Dispositifs électroluminescents polychromatiques et matrice de transport de trous polyvalente pour lesdits dispositifs
CN106414394A (zh) * 2014-03-25 2017-02-15 诺瓦尔德股份有限公司 多色发光器件及其通用空穴传输基质
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WO2016058504A1 (fr) * 2014-10-13 2016-04-21 江苏和成新材料有限公司 Dérivé d'amine aromatique et dispositif électroluminescent organique correspondant
US10644247B2 (en) 2015-02-06 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
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EP3392246A4 (fr) * 2015-12-08 2019-10-30 Heesung Material Ltd. Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé
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JP2018118933A (ja) * 2017-01-26 2018-08-02 株式会社リコー エレクトロクロミック化合物、エレクトロクロミック組成物およびエレクトロクロミック素子
US10975296B2 (en) 2017-01-26 2021-04-13 Ricoh Company, Ltd. Electrochromic compound, electrochromic composition, and electrochromic element
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JP2020535645A (ja) * 2017-09-25 2020-12-03 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロルミネッセンス化合物及びそれを含む有機エレクトロルミネッセンスデバイス
US11450814B2 (en) 2017-09-25 2022-09-20 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
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