WO2015068987A1 - Nouveau composé organique, et élément électroluminescent organique et dispositif électronique comprenant ce composé - Google Patents

Nouveau composé organique, et élément électroluminescent organique et dispositif électronique comprenant ce composé Download PDF

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WO2015068987A1
WO2015068987A1 PCT/KR2014/010385 KR2014010385W WO2015068987A1 WO 2015068987 A1 WO2015068987 A1 WO 2015068987A1 KR 2014010385 W KR2014010385 W KR 2014010385W WO 2015068987 A1 WO2015068987 A1 WO 2015068987A1
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substituted
unsubstituted
alkyl
alkyl group
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강지승
유영준
서하나
이예림
이대균
한근희
현승학
안중복
박노길
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(주)씨에스엘쏠라
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Priority claimed from KR1020140141900A external-priority patent/KR101559428B1/ko
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Priority to CN201480061102.2A priority Critical patent/CN105722826B/zh
Publication of WO2015068987A1 publication Critical patent/WO2015068987A1/fr

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Definitions

  • the present invention relates to a novel organic compound, an organic light emitting display device, and an electronic device including the same.
  • an organic electric device refers to a device that requires charge exchange between an electrode and an organic material using holes and electrons.
  • organic electric devices include organic transistors, organic solar cells, organic photoconductors (OPCs), and organic light emitting devices, all of which require light emitting materials, electron injection or transport materials, hole injection or transport materials to drive the devices.
  • OPCs organic photoconductors
  • the light emitting material is the most important material that determines the performance of the light emission efficiency and life. There are several characteristics required for such light emitting materials, such as high quantum fluorescence yield in solid state, high mobility of electrons and holes, not easy decomposition during vacuum deposition, uniform film formation, It should be stable.
  • Materials used as the organic material layer in the organic electric element may be divided into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function.
  • the maximum light emission wavelength may be shifted to a long wavelength due to the interaction of molecules, and thus color purity may be reduced or efficiency may be reduced due to the light emission attenuation effect.
  • a host / dopant system may be used as the light emitting material.
  • U.S. Patent No. US5153073 discloses an electroluminescent device using a pyrene-based compound substituted with a diphenyl amine derivative, but the blue color purity is often lowered to give a bluish green light, but the efficiency when blue light emission occurs. There is a disadvantage that the brightness is lower.
  • the center has a diphenylanthracene structure, and a blue light emitting compound in which an aryl group is substituted at the end and an organic light emitting device using the same are disclosed, but the light emitting efficiency and luminance are not sufficient. There was this.
  • WO 2005/108348 A1 discloses aromatic amine derivatives in which a substituted or unsubstituted diphenylamine group is directly substituted with a pyrene-based compound, but a light emission wavelength other than pure blue because the aryl or alkyl group is directly substituted in the pyrene ring. There is a problem of bluish green light moved to this long wavelength.
  • One embodiment of the present invention provides a novel tetrahydrophenalenoacridine-based organic compound that can be applied to an organic electroluminescent device, particularly an organic electroluminescent device.
  • Another embodiment of the present invention includes the tetrahydrophenalenoacridine-based organic compound to provide an organic light emitting device having improved long life, high brightness, efficiency and color purity.
  • Another embodiment of the present invention provides an electronic device to which the organic light emitting device is applied.
  • an organic compound represented by Chemical Formula 1 is provided.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group and a substituted or unsubstituted naphthyl group.
  • the substituent is hydrogen, deuterium (D), halogen, CN, Si (CH 3 ) 3 , CF 3 , nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted It may include at least one selected from the group consisting of a ring C3 ⁇ C10 cycloalkyl group, substituted or unsubstituted C1 ⁇ C10 alkoxy group, phenyl group, pyridyl group and pyrimidyl group;
  • Ar 1 and Ar 2 may be bonded to each other to form C 3 to C 5 cycloalkyl to form a spiro structure in which a carbon atom bonded to Ar 1 and Ar 2 is a spiro atom;
  • R1, R2, R3 and R4 are each independently hydrogen; heavy hydrogen; halogen; CN; Si (CH 3 ) 3 ; CF 3 ; Nitro; A substituted or unsubstituted C1-C40 alkyl group, a C5-C40 aryl group, a C4-C40 heteroaryl group, a C3-C40 cycloalkyl group, or a C3-C40 heterocycloalkyl group, wherein R1, R2, R3, and R4 are substituted
  • the substituents are deuterium, halogen, CN, Si (CH 3 ) 3 , CF 3 , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group and substituted or unsubstituted C1-C10 alkoxy At least one selected from the group consisting of groups;
  • L is a single bond, a substituted or unsubstituted C5 to C40 arylene group, or a C4 to C40 heteroarylene group, and when L is substituted, the substituent is deuterium, halogen, CN, Si (CH 3 ) 3 , CF 3 , At least one selected from the group consisting of a nitro, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted C1-C10 alkoxy group;
  • Z is absent, single bond, Si (CH 3 ) 2 , divalent amine group, substituted or unsubstituted C1 to C5 alkylene group, or substituted or unsubstituted C2 to C5 alkenylene group, and Z is substituted
  • the substituent in the case where it is selected includes at least one selected from the group consisting of a C1 to C40 alkyl group, a C5 to C40 aryl group, a C4 to C40 heteroaryl group and a C3 to C40 cycloalkyl group;
  • R5 and R6 are each independently a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C5-C40 aryl group, a substituted or Unsubstituted C6 to C40 arylalkyl group, substituted or unsubstituted C5 to C40 heteroaryl group, substituted or unsubstituted C3 to C40 cycloalkyl group or substituted or unsubstituted C3 to C40 heterocycloalkyl group, the R5 and Substituents when R6 is substituted are deuterium, halogen, CN, Si (CH 3 ) 3 , CF 3 , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubsti
  • R5 and R6 are each independently substituted with a substituted or unsubstituted C1-C40 alkylene group, a C2-C40 alkenylene group substituted with a C1-C10 alkyl group, and a C1-C10 alkyl group.
  • the carbon atom or heteroatom of R5 or R6 is bonded to an adjacent pyrenyl structure and a linker X, and together with the nitrogen atom to which R5 or R6 is bonded and the linker X, a C1 to C40 alkyl group and a C5 to C40 aryl group And fused or condensed, 5- or 6-membered rings substituted or unsubstituted with a C5-C40 heteroaryl group,
  • the linker X is selected from the group consisting of N (Y1) and C (Y2) (Y3), wherein Y1, Y2 and Y3 are each independently a group consisting of a hydrogen atom, a C1-C10 alkyl group and a C5-C10 aryl group Is selected from,
  • hetero atoms included in the heteroaryl, the heteroalkyl, the heteroarylene, and the heteroalkylene include at least one selected from the group consisting of N, O, S, Se, and Si.
  • an organic electroluminescent device in which an organic thin film layer composed of one or more layers including at least a light emitting layer is sandwiched between a cathode and an anode,
  • At least one or more layers of the organic thin film layers provide an organic electroluminescent device containing the organic compound alone or in combination of two or more thereof.
  • an electronic device including the organic light emitting device is provided.
  • the organic electroluminescent device using the organic compound may realize high luminous efficiency, high luminous brightness, high color purity and significantly improved luminous lifetime.
  • 5 is a PL (PhotoLuminescence) graph of the compound [1] prepared in the Example.
  • the organic compound is a compound used in an organic light emitting device, and is not necessarily limited to a compound capable of emitting light, and its application range is not limited to an organic light emitting layer, and an organic electric field such as a charge injection layer and a charge transport layer. All layers may be used in any layer constituting the light emitting device.
  • the term 'organic compound' and 'optical device' are used herein in consideration of the case where the present invention is applied to both an organic light emitting device and a device for photovoltaic power generation regardless of a dictionary or customary definition.
  • alkyl groups include both straight and branched chains, unless defined otherwise.
  • an organic compound represented by Chemical Formula 1 is provided.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group and a substituted or unsubstituted naphthyl group.
  • the substituent is hydrogen, deuterium (D), halogen, CN, Si (CH 3 ) 3 , CF 3 , nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted It may include at least one selected from the group consisting of a ring C3 ⁇ C10 cycloalkyl group, substituted or unsubstituted C1 ⁇ C10 alkoxy group, phenyl group, pyridyl group and pyrimidyl group;
  • Ar 1 and Ar 2 may be bonded to each other to form C 3 to C 5 cycloalkyl to form a spiro structure in which a carbon atom bonded to Ar 1 and Ar 2 is a spiro atom;
  • R1, R2, R3 and R4 are each independently hydrogen; heavy hydrogen; halogen; CN; Si (CH 3 ) 3 ; CF 3 ; Nitro; A substituted or unsubstituted C1-C40 alkyl group, a C5-C40 aryl group, a C4-C40 heteroaryl group, a C3-C40 cycloalkyl group, or a C3-C40 heterocycloalkyl group, wherein R1, R2, R3, and R4 are substituted
  • the substituents are deuterium, halogen, CN, Si (CH 3 ) 3 , CF 3 , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group and substituted or unsubstituted C1-C10 alkoxy At least one selected from the group consisting of groups;
  • L is a single bond, a substituted or unsubstituted C5 to C40 arylene group, or a C4 to C40 heteroarylene group, and when L is substituted, the substituent is deuterium, halogen, CN, Si (CH 3 ) 3 , CF 3 , At least one selected from the group consisting of a nitro, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted C1-C10 alkoxy group;
  • Z is absent, a single bond, Si (CH 3) 2, a bivalent amine group, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted alkenylene group of the unsubstituted C2 ⁇ C5 of C1 ⁇ C5 ring, wherein Z is a substituted
  • the substituent in the case where it is selected includes at least one selected from the group consisting of a C1 to C40 alkyl group, a C5 to C40 aryl group, a C4 to C40 heteroaryl group and a C3 to C40 cycloalkyl group;
  • R5 and R6 are each independently a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C5-C40 aryl group, a substituted or Unsubstituted C6 to C40 arylalkyl group, substituted or unsubstituted C5 to C40 heteroaryl group, substituted or unsubstituted C3 to C40 cycloalkyl group or substituted or unsubstituted C3 to C40 heterocycloalkyl group, the R5 and Substituents when R6 is substituted are deuterium, halogen, CN, Si (CH 3 ) 3 , CF 3 , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubsti
  • R5 and R6 are each independently substituted with a substituted or unsubstituted C1-C40 alkylene group, a C2-C40 alkenylene group substituted with a C1-C10 alkyl group, and a C1-C10 alkyl group.
  • the carbon atom or heteroatom of R5 or R6 is bonded to an adjacent pyrenyl structure and a linker X, and together with the nitrogen atom to which R5 or R6 is bonded and the linker X, a C1 to C40 alkyl group and a C5 to C40 aryl group And fused or condensed, 5- or 6-membered rings substituted or unsubstituted with a C5-C40 heteroaryl group,
  • the linker X is selected from the group consisting of N (Y1) and C (Y2) (Y3), wherein Y1, Y2 and Y3 are each independently a group consisting of a hydrogen atom, a C1-C10 alkyl group and a C5-C10 aryl group Is selected from,
  • hetero atoms included in the heteroaryl, the heteroalkyl, the heteroarylene, and the heteroalkylene include at least one selected from the group consisting of N, O, S, Se, and Si.
  • the organic compound represented by Chemical Formula 1 may be used in an organic electroluminescent device to implement an organic electroluminescent device having characteristics of excellent luminous efficiency, luminescence brightness, color purity, and luminescence lifetime, or used in a photovoltaic device for solar power generation. It can be used as a photo compound.
  • the organic compound represented by Chemical Formula 1 may be used for various organic film layers between the first electrode and the second electrode, such as an electron transport layer (ETM), an emission layer (EML), a hole transport layer (HTM), etc. of an organic light emitting diode.
  • ETM electron transport layer
  • EML emission layer
  • HTM hole transport layer
  • OLED organic light emitting diode
  • R 1 represents a hydrogen atom, a C 1 to C 10 alkyl group, a C 3 to C 10 cycloalkyl group,
  • X 1 is selected from the group consisting of N (Y 1) and C (Y 2) (Y 3), wherein Y 1, Y 2 and Y 3 are each independently a group consisting of a hydrogen atom, a C 1 -C 10 alkyl group and a C 5 -C 10 aryl group Is selected from;
  • R7 and R8 are each independently hydrogen, deuterium, halogen, CN, CF 3 , nitro, C1-C20 straight or branched chain alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-C10 alkoxy, amino , C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10 alkyl) silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl, and C3-C10 heterocycloalkyl, n and m are integers of 1-5;
  • R2, R3, and R4 are each independently hydrogen or a substituted or unsubstituted C1-C10 alkyl group
  • R5 and R6 are each independently a hydrogen atom, a C1-C10 alkyl group,
  • X 1 is selected from the group consisting of O, S, N (Y 1) and C (Y 2) (Y 3), wherein Y 1, Y 2 and Y 3 are each independently a hydrogen atom, a C 1 -C 10 alkyl group, and C 5 -C 10 Selected from the group consisting of aryl groups,
  • R a and R b are each independently hydrogen, deuterium, halogen, CN, -OH, CF 3 , nitro, C1-C20 linear or branched alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-C10 alkoxy, amino, C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10) C10 alkyl) silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl, and C3-C10 heterocycloalkyl, k and l are 1 An integer from to 4;
  • P is CH 2 or a carbon atom unsubstituted or substituted with one or two C1 to C10 alkyl groups
  • R a and R b are each independently hydrogen, deuterium, halogen, CN, -OH, CF 3 , nitro, C1-C20 linear or branched alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-- C10 alkoxy, amino, C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10 alkyl ) Silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl and C3-C10 heterocycloalkyl, k and
  • R 5, R 6 and linker X may be fused or Organic compounds characterized by being able to form condensed rings:
  • R9 is a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C2 to C40 alkenyl group, a substituted or unsubstituted C5 to C40 aryl group, a substituted or unsubstituted C6 to C40 arylalkyl group, a substituted or unsubstituted A C5 to C40 heteroaryl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, or a substituted or unsubstituted C3 to C40 heterocycloalkyl group,
  • the two bonding positions are linked to two adjacent carbons in the pyrenyl structure of Formula 1 to form a fused or condensed six-membered ring.
  • Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group and a substituted or unsubstituted naphthyl group, and when Ar1 and Ar2 are substituted Substituent of is at least one selected from the group consisting of deuterium, halogen, CN, Si (CH 3 ) 3 , CF 3 , a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group and a phenyl group May comprise;
  • R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted C 3 A cycloalkyl group of -C10, wherein the substituent when R1 is substituted is deuterium or Si (CH 3 ) 3 ;
  • R ⁇ 2>, R ⁇ 3>, R ⁇ 4> is respectively independently hydrogen or a C1-C10 alkyl group
  • L is a single bond or a phenylene group
  • X 1 is O, S, N, Se, Si (alkyl of C1 ⁇ C10) 2 , N (Y1), C (Y2) (Y3), C (Y2) (Y3) -C (Y2) (Y3) , And Si (Y2) (Y3), wherein Y1, Y2, and Y3 are each independently selected from the group consisting of a hydrogen atom, a C1-C10 alkyl group, and a phenyl group,
  • P is CH 2 or a carbon atom unsubstituted or substituted with one or two C1 to C10 alkyl groups
  • Ra and Rb are each independently hydrogen or phenyl
  • R 5, R 6 and the linker X may be fused or Organic compounds characterized by being able to form condensed rings:
  • X is a carbon atom substituted or unsubstituted with one or two phenyl groups
  • R10 is a phenyl group unsubstituted or substituted with a C1 to C10 alkyl group
  • R a is hydrogen or a C1-C20 straight or branched alkyl group
  • the two bonding positions are linked to two adjacent carbons in the pyrene structure of Formula 1 to form a fused or condensed six-membered ring.
  • the organic compound may have a chemical structure of any one of Compounds 1 to 185 shown in the following First Table.
  • the organic compound represented by Chemical Formula 1 including Compound 1 to Compound 185 may be synthesized by using a synthesis method that is obviously predicted from or by referring to Schemes of the following Synthesis Example. For examples of more detailed synthetic routes of these compounds, see the schemes of the following synthesis examples.
  • Compounds 1 to 185 are suitable for use in organic membranes of organic electroluminescent devices, particularly hole transport layers, hole injection layers or light emitting layers.
  • the organic layer may be formed by a soluble process using the organic compound represented by Chemical Formula 1.
  • the organic compound represented by Formula 1 may be used as the emission layer material, specifically, may be used as a fluorescent blue dopant material.
  • the structure of the organic light emitting device is very diverse.
  • One or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer and an electron injection layer may be further included between the first electrode and the second electrode.
  • the organic light emitting device More specifically, in one embodiment of the organic light emitting device,
  • the organic light emitting device may have a structure consisting of a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode,
  • the organic light emitting device may have a structure consisting of a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode,
  • the organic light emitting diode may have a structure of a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode.
  • At least one of the hole transport layer, the hole injection layer and the light emitting layer may include an organic compound represented by the formula (1).
  • the emission layer of the organic light emitting diode may include a phosphorescent or fluorescent dopant including red, green, blue or white.
  • the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.
  • the compound represented by Formula 1 may also be used as a fluorescent dopant in the light emitting layer.
  • a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode.
  • the first electrode may be an anode.
  • a substrate used in a conventional organic electroluminescent device is used, but a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable.
  • Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.
  • a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 -5 to 10 -3 torr, a deposition rate of 0.01 to 100 Pa / sec, and a film thickness are appropriately selected in the range of usually 100 Pa to 1 ⁇ m.
  • the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm.
  • the heat treatment temperature for removing the solvent is preferably selected from a temperature range of about 80 ° C to 200 ° C.
  • the hole injection layer material may be a compound represented by Chemical Formula 1.
  • phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or the starburst type amine derivatives described in Advanced Material, 6, p.677 (1994), for example, TCTA, m-MTDATA, m-.
  • the hole injection layer may have a thickness of about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.
  • the hole injection layer may be formed by vacuum vapor deposition.
  • specific deposition conditions depend on the compound used, they are selected from the range of conditions substantially the same as the formation of a general hole injection layer.
  • DNTPD N, N-bis- [4- (di-m-tolylamino) phenyl] -N, N-diphenylbiphenyl-4,4-diamine
  • DNTPD N-bis- [4- (di-m-tolylamino) phenyl] -N, N-diphenylbiphenyl-4,4-diamine
  • a hole transport layer may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB.
  • the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from a range of conditions almost the same as that of the formation of the hole injection layer.
  • the hole transport layer material may include a compound represented by Formula 1 as described above.
  • carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'- diphenyl- [1,1-biphenyl]
  • Conventional amine derivatives having aromatic condensed rings such as -4,4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (? -NPD), and the like
  • TPD -4,4'-diamine
  • N, N'-di (naphthalen-1-yl) -N N'-diphenyl benzidine
  • ? -NPD N'-diphenyl benzidine
  • the hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be degraded, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.
  • the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like.
  • the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.
  • the light emitting layer may include the compound represented by Chemical Formula 1 as described above.
  • the compound represented by Formula 1 may be used with a suitable known host material, or may be used with a known dopant material.
  • IDE102 As the fluorescent dopant, IDE102, IDE105, and C545T available from Hayashibara, Inc., which are available from Idemitsu, can be used, and red phosphorescent dopants PtOEP, RD61 of UDC, and green phosphorescent dopant Ir can be used.
  • MQD N-methylquinacridone
  • coumarin Coumarine
  • Doping concentration is not particularly limited, but the content of the dopant is generally 0.01 to 15 parts by weight based on 100 parts by weight of the host.
  • the thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa.
  • the thickness of the light emitting layer is less than 100 kW, the light emission characteristics may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.
  • the light emitting layer when the light emitting compound is used together with the phosphorescent dopant, a method such as vacuum deposition, spin coating, cast method, LB method, or the like is applied on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer.
  • the hole blocking layer HBL may be formed.
  • the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer.
  • Known hole blocking materials that can be used include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and BCP.
  • the hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase. The hole blocking layer may be omitted.
  • the electron transport layer is formed using various methods such as vacuum deposition, spin coating, and casting.
  • the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer.
  • the electron transport layer material functions to stably transport electrons injected from an electron injection electrode (Cathode), and a quinoline derivative, particularly tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, PBD and the like are known. Materials may also be used.
  • the electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.
  • an electron injection layer which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, which does not particularly limit the material.
  • any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO, or the like can be used.
  • the deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from the range of conditions almost the same as the formation of the hole injection layer.
  • the electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 50 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.
  • the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method.
  • the second electrode may be used as a cathode.
  • a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned.
  • a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.
  • reaction example a reaction example and a comparative example are illustrated concretely, this invention is not limited to the following synthesis example and an Example.
  • the intermediate compound is indicated by adding a serial number to the number of the final product.
  • compound 1 is represented by compound [1]
  • the intermediate compound of the said compound is described by [1-1] etc.
  • the chemical number is indicated as the chemical formula number.
  • the compound represented by the formula (1) is represented by compound 1.
  • 5 is a PL (PhotoLuminescence) graph of the compound [1] prepared above.
  • compound b represented by the following formula b as a fluorescent blue dopant
  • 2-TNATA 4,4 ', 4 "-tris (N-naphthalen- 2-yl) -N-phenylamino) -triphenylamine
  • ⁇ -NPD N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine
  • An organic light emitting device having the following structure was prepared: ITO / 2-TNATA (80 nm) / ⁇ -NPD (30 nm) / Compound a + Compound b (30 nm) / Alq 3 (30 nm) / LiF (1 nm). / Al (100 nm).
  • Anode cuts Corning's 15 ⁇ / cm 2 (1000 ⁇ ) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing.
  • 2-TANATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm.
  • ⁇ -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm.
  • Compound a represented by Formula a and Compound b represented by Formula b (5% doping) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm.
  • Comparative Sample 1 LiF 1 nm (electron injection layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in [First Table Group (Group)]. This is called Comparative Sample 1.
  • Comparative Example 1 Compound 3, 7, 15, 22, 28, 35, 43, 56, 58, 88, 95, 101, 113, 117, 121 in the first table group instead of compound b as the light emitting layer fluorescent dopant compound.

Abstract

L'invention concerne un composé organique représenté par la formule chimique 1 dans la description (voir image dans la description) et un élément électroluminescent organique le comprenant.
PCT/KR2014/010385 2013-11-08 2014-10-31 Nouveau composé organique, et élément électroluminescent organique et dispositif électronique comprenant ce composé WO2015068987A1 (fr)

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WO2016186276A1 (fr) * 2015-05-20 2016-11-24 삼성에스디아이 주식회사 Composé organique, élément optoélectronique organique et dispositif d'affichage
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10538538B2 (en) 2017-01-13 2020-01-21 Samsung Display Co., Ltd. Polycyclic compound and organic electroluminescence device including the same
US20200048207A1 (en) * 2017-03-13 2020-02-13 Merck Patent Gmbh Compounds with arylamine structures
US10673000B2 (en) 2016-11-14 2020-06-02 Samsung Display Co., Ltd. Heterocyclic compound and organic electroluminescence device including the same

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WO2016186276A1 (fr) * 2015-05-20 2016-11-24 삼성에스디아이 주식회사 Composé organique, élément optoélectronique organique et dispositif d'affichage
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10673000B2 (en) 2016-11-14 2020-06-02 Samsung Display Co., Ltd. Heterocyclic compound and organic electroluminescence device including the same
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US20200048207A1 (en) * 2017-03-13 2020-02-13 Merck Patent Gmbh Compounds with arylamine structures

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