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WO2013108997A1 - Composé pour dispositif électronique organique, dispositif électronique organique et appareil électronique le comprenant - Google Patents

Composé pour dispositif électronique organique, dispositif électronique organique et appareil électronique le comprenant Download PDF

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WO2013108997A1
WO2013108997A1 PCT/KR2012/011234 KR2012011234W WO2013108997A1 WO 2013108997 A1 WO2013108997 A1 WO 2013108997A1 KR 2012011234 W KR2012011234 W KR 2012011234W WO 2013108997 A1 WO2013108997 A1 WO 2013108997A1
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group
aryl
deuterium
substituted
heterocyclic
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Korean (ko)
Inventor
박정환
이선희
문성윤
김대성
정화순
김원삼
변지훈
이범성
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Samsung Display Co Ltd
Duksan Hi Metal Co Ltd
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Samsung Display Co Ltd
Duksan Hi Metal Co Ltd
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Priority claimed from KR1020120118629A external-priority patent/KR101498278B1/ko
Application filed by Samsung Display Co Ltd, Duksan Hi Metal Co Ltd filed Critical Samsung Display Co Ltd
Priority to US14/362,406 priority Critical patent/US9373806B2/en
Publication of WO2013108997A1 publication Critical patent/WO2013108997A1/fr
Anticipated expiration legal-status Critical
Priority to US15/170,475 priority patent/US20160276599A1/en
Priority to US15/187,203 priority patent/US9716236B2/en
Ceased legal-status Critical Current

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    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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    • C07—ORGANIC CHEMISTRY
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    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • H05B33/00—Electroluminescent light sources
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
  • a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
  • materials forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting auxiliary layer material, a light emitting material, an electron transport material, an electron injection material, etc., are stable and efficient. Supported by the material should be preceded, but the development of a stable and efficient organic material layer for an organic electric device has not been made enough, and therefore, the development of new materials is still required.
  • An object of the present invention is to provide a compound containing an five-membered hetero ring capable of improving the luminous efficiency, low driving voltage, color purity, and lifetime of the device, an organic electric device using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • the driving voltage of the device can be lowered, and color purity, luminous efficiency and lifetime can be greatly improved.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • halo or halogen as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.
  • alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
  • alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • the aryl group or arylene group in the present invention means a monocyclic or heterocyclic aromatic, for example, the aryl group may be a phenyl group, biphenyl group, fluorene group, spirofluorene group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only a single ring but also a heterocycle, and adjacent groups may be formed by bonding.
  • heterocycloalkyl and “heterocyclic group” include one or more heteroatoms, unless otherwise specified, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. Adjacent groups may be formed in combination.
  • heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
  • heteroatom refers to at least one of N, O, S, P, and Si unless otherwise indicated.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • saturated or unsaturated ring as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy group, C 1 ⁇ C 20 alkyl amine group, C 1 ⁇ C 20 coming of the alkyl group, C 6 ⁇ C 20 coming aryl Ti, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 of the Alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron group, It means that it is substituted with one or more substituents selected from the group consisting of a germanium group, and a C 5 ⁇ C 20 heterocyclic group
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • An organic material layer containing a compound represented by the formula (1) between) is provided.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
  • the compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound of the present invention may be used as the light emitting layer 150, hole transport layer 140 and / or light emitting auxiliary layer 151.
  • the hole transport layer in the organic electroluminescent device it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each of the light emitting layers R, G, and B, It is time to develop different emission auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.
  • a light emitting layer or an auxiliary light emitting layer using a compound represented by the formula (1) by optimizing the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) of the organic material
  • the life and efficiency of the electric device can be improved at the same time.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic layer may be prepared by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer. It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • R 1 to R 4 and R 11 to R 14 are each independently selected from hydrogen, deuterium, halogen, C 6 ⁇ C 60 aryl group, fluorenyl group, C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 Fused ring group of aromatic ring, C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, -LN (R ') (R "), C 1 ⁇ C It is selected from the group consisting of an alkyl group of 50, an alkenyl group of C 2 to C 20 , an alkoxy group of C 1 to C 30 , and an aryloxy group of C 6 to C 30 .
  • R 21 and R 22 are each independently i) a hydrogen, C 6 ⁇ C 60 aryl group, fluorenyl group, C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring, O , C 2 -C 60 heterocyclic group including at least one hetero atom of N, S, Si and P and -LN (R ') (R "), or ii) Form a monocyclic or polycyclic ring.
  • R 1 to R 4 and R 11 to R 14 may both be hydrogen at the same time, and R 21 and R 22 may be bonded to each other to form a ring. Otherwise, at least one of R 1 to R 4 is not hydrogen and at least one of R 11 to R 14 is not hydrogen at the same time.
  • R 21 and R 22 are bonded to each other to form a ring, it is important that they are bonded to each other to form a ring, and thus the scope of the present invention is not limited by the substituents and the reaction to form the ring. Does not.
  • the ring formed by combining R 21 and R 22 with each other may be not only an aromatic ring or a hetero ring including at least one hetero atom, but also a form in which an aromatic ring and an aliphatic ring are fused together.
  • R 21 and R 22 may be bonded to each other to form an aromatic ring such as benzene, naphthalene, phenanthrene, and the like.
  • the aromatic ring has 6 to 60 carbon atoms.
  • R 21 and R 22 may be bonded to each other to form a heterocycle such as thiophene, furan, pyridine, indole, quinoline, and the like, wherein the carbon number may be 2 to 60.
  • the ring may be fused to each other, a plurality of rings may not be fused to each other, or a ring in which the fused and non-fused forms are mixed.
  • X and Y are each independently S, O or SiR 31 R 32 .
  • R 31 and R 32 are independently of each other hydrogen, a C 6 ⁇ C 60 aryl group, C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P, Or a C 1 to C 50 alkyl group.
  • L is a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And divalent aliphatic hydrocarbon group; It is selected from the group consisting of.
  • Ar is a C 2 -C 60 heterocyclic group, a C 6 -C 60 aryl group or -N (R ') (R ") containing at least one heteroatom of O, N, S, Si and P. .
  • R 'and R "defined in R 1 ⁇ R 4 and R 11 ⁇ R 14 , R 21 and R 22 , Ar and the like are independently of each other at least one heteroatom of O, N, S, Si and P It may include a C 2 ⁇ C 20 heterocyclic group, C 6 ⁇ C 20 An aryl group or a fluorenyl group.
  • Ar, R 'and R "are aryl groups they are deuterium, halogen, silane group, boron group, germanium group, cyano group, nitro group, C One ⁇ C 20 Alkylthio, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • Ar, R 'and R "are heterocyclic groups they are deuterium, halogen, silane, cyano, nitro, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R 1 to R 4 , R 11 to R 14 , R 21 , R 22 , R 'and R ′′ are fluorenyl groups, they are deuterium, halogen, silane group, cyano group, C 1 to C 20 alkyl group, C for 2 ⁇ C 20 of alkenyl groups (alkenyl), C 6 ⁇ C 20 aryl group, a C 6 ⁇ C 20 aryl group, C 2 ⁇ C 20 heterocyclic group and C 3 ⁇ C 20 substituted by deuterium May be substituted with one or more substituents selected from the group consisting of cycloalkyl groups,
  • R One ⁇ R 4 , R 11 ⁇ R 14 , R 21 And R 22 In the case of the fused ring group, it is deuterium, halogen, silane group, boron group, germanium group, cyano group, nitro group, C One ⁇ C 20 Alkylthio, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R One ⁇ R 4 , R 11 ⁇ R 14 , R 31 And R 32 When is an alkyl group, it is halogen, silane group, boron group, cyano group, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R One ⁇ R 4 And R 11 ⁇ R 14 Is an alkenyl group, it is a deuterium, a halogen, a silane group, a cyano group, C One ⁇ C 20 Alkoxyl, C One ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl, C 6 ⁇ C 20 Aryl group of C, substituted with deuterium 6 ⁇ C 20 Aryl group, C 2 ⁇ C 20 Heterocyclic group, C 3 ⁇ C 20 Cycloalkyl group, C 7 ⁇ C 20 of Arylalkyl group and C 8 ⁇ C 20 May be substituted with one or more substituents selected from the group consisting of arylalkenyl groups,
  • R 1 to R 4 and R 11 to R 14 are an alkoxyl group
  • this is deuterium, halogen, silane group, C 1 ⁇ C 20 alkyl group, C 6 ⁇ C 20 aryl group, C 6 ⁇ substituted with deuterium C 20 may be substituted with one or more substituents selected from the group consisting of an aryl group, C 2 ⁇ C 20 heterocyclic group and C 3 ⁇ C 20 cycloalkyl group,
  • R 1 ⁇ R 4 and R 11 ⁇ R, if 14 is an aryloxy group which is substituted C with deuterium, a silane group, a cyano group, C 1 ⁇ C 20 alkyl group, an aryl group, a heavy hydrogen of C 6 ⁇ C 20 of 6 It may be substituted with one or more substituents selected from the group consisting of an aryl group of ⁇ C 20 , a heterocyclic group of C 2 ⁇ C 20 and a cycloalkyl group of C 3 ⁇ C 20 .
  • the compound represented by Chemical Formula 1 may be represented by one of the following chemical formulas.
  • Ar ' is hydrogen, deuterium, halogen, C 1 ⁇ C 20 Alkyl group, C 2 ⁇ C 20 Alkenyl group, C 1 ⁇ C 20 Alkoxy group, -LN (R') ( R "), an arylalkenyl group of C 6 ⁇ C 20 aryl group, a C 6 ⁇ C 20 aryl group, C 7 ⁇ C 20 aryl group, C 8 ⁇ C 20 substituted by deuterium, C 2 ⁇ C 20 Is selected from the group consisting of a heterocyclic group, a nitrile group and an acetylene group,
  • X 1 to X 4 are CR 41 or N.
  • R 41 may be hydrogen, deuterium, an aryl group of C 6 ⁇ C 20 or a heterocyclic group of C 2 ⁇ C 20 , R 1 ⁇ R 4 , R 11 ⁇ R 14 , R 21 , R 22 , R ' , R ", X, Y, L and Ar are as defined in formula (1),
  • the compound represented by Formula 1 or 2 may be one of the following compounds.
  • the compound according to the present invention is prepared by reacting one of Sub 1 to Sub 4 with Sub 5, as in Scheme 1 below.
  • Scheme 1 a case where X is S will be described by way of example, but when X is O or Si, it is similar to the following synthesis method and will not be described separately.
  • R 1 is one of R 1 to R 4 described in Formula 1
  • R 2 is R 21 or R 22
  • R 3 is one of R 11 to R 14 .
  • Dibenzothiophene derivatives substituted with R 1 and R 2 were dissolved in a carbon disulfide solvent in a nitrogen atmosphere, and bromine was slowly added dropwise. After stirring at room temperature for 12 hours, when the reaction was completed, the organic solvent was concentrated using a pressure reduction apparatus and the resulting product was recrystallized using ethanol solvent to obtain the desired Sub 1-1.
  • Sub 2-1 was dissolved in acetic acid, and hydrogen peroxide dissolved in acetic acid was added dropwise, followed by stirring at room temperature for 6 hours. Upon completion of the reaction, acetic acid was removed using a decompression device and separated using a Silicagel column to obtain the desired Sub 2-2.
  • Sub 2-3 was carried out similarly to the synthesis method of Sub 1-2, to obtain Sub 2-4.
  • the obtained Sub 2-5 was processed in the same manner as in the synthesis of Sub 1 to obtain a desired Sub 2.
  • Sub 3-2 was obtained in the same manner as in the synthesis of Sub 1, to obtain a desired sub 3.
  • Sub 4-1 was carried out in the same manner as in the synthesis of Sub 2-2, to obtain a desired Sub 4-2.
  • the obtained Sub 4-2 was carried out in the same manner as the synthesis method of Sub 2-3 to obtain the desired Sub 4-3.
  • Sub 4-3 was processed in the same manner as the synthesis method of Sub 1-2 to obtain Sub 4-4.
  • the obtained Sub 4-4 was processed in the same manner as in the synthesis of Sub 1 to obtain a desired Sub 4.
  • the compounds according to the present invention can be synthesized by Reaction Schemes 1 and 2. Examples of synthesizing the compound of the present invention in two ways are as follows.
  • Sub 11-1 or Sub 11-2 (1 equiv) was dissolved in THF in a round bottom flask, then Sub 9 (1.2 equiv), Pd (PPh 3 ) 4 (0.03 equiv), NaOH (3 equiv) and water were added After stirring, the mixture was refluxed. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain a product product.
  • Sub 5 is as follows, but is not limited thereto.
  • Sub 9 is as follows, but is not limited thereto.
  • Sub 10 is as follows, but is not limited thereto.
  • O-atomic hetero compounds (8.5 g, 20 mmol) and 4- (4-bromophenyl) -2,6-diphenylpyrimidine (9.3 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol) , P ( t -Bu) 3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol) were prepared in the same manner as in Synthesis of Product 1-1 to 9.2 g of product 2-31 (yield 63%) Got.
  • Heteroatomic hetero compounds (8.6 g, 20 mmol) and 2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g , 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol) were prepared in the same manner as in Synthesis of Product 1-1 to 8.5 g ( Yield 64%).
  • O-atomic hetero compounds (9.5 g, 20 mmol) and 4-bromobiphenyl (5.6 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaOt-Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-1, to obtain 8.2 g (yield 65%) of product 4-19.
  • O-atomic hetero compounds (6.5 g, 20 mmol) with 2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the above Product 1-1 synthesis to obtain 7.2 g (yield 68%) of Product 3-28.
  • O-atomic hetero compounds (6.5 g, 20 mmol) with 2-bromo-4-phenylquinazoline (10.5 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-1, to obtain 8.7 g (yield 64%) of Product 3-38.
  • O-atomic hetero compounds (6.5 g, 20 mmol) and 2- (3-bromophenyl) -4-phenylquinazoline (8.7 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol) , P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in Synthesis of Product 1-1 to 7.4 g of Product 3-44 (yield 61%). )
  • O-atomic hetero compounds (6.5 g, 20 mmol) with 2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were prepared in the same manner as in the synthesis of Product 1-1, to obtain 7.1 g (yield 67%) of Product 4-28.
  • O-atomic hetero compounds (6.5 g, 20 mmol) and 4-([1,1'-biphenyl] -3-yl) -2-bromopyrido [3,2-d] pyrimidine (8.7 g, 24 mmol), toluene ( 210 mL), Pd 2 (dba) 3 (0.92 g, 1 mmol), P ( t -Bu) 3 (0.4 g, 2 mmol), NaO t -Bu (5.8 g, 60 mmol) was obtained from Product 1-1. In the same manner as in the synthesis method of 7.5g (yield 62%) of Product 7-4 was obtained.
  • an organic light emitting device was manufactured according to a conventional method.
  • a phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a hole injection layer having a thickness of 60 nm.
  • (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer.
  • BAlq (2-methyl-8-quinoline oleito) aluminum
  • Alq 3 tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form Al / LiF as a cathode, thereby manufacturing an organic EL device.
  • the organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that Comparative Compound 1 (4,4'-di (9H-carbazol-9-yl) -1,1'-biphenyl) was used as a light emitting host material. Was produced.
  • Comparative Compound 2 (9- (9- (4,6-diphenylpyrimidin-2-yl) -9H-carbazol-3-yl) -12-phenyl-12H-benzo [4,5] thieno [3] as a light emitting host material , 2-a] carbazole), except that the organic electroluminescent device was manufactured in the same manner as in Experiment 1.
  • Comparative Compound 3 (3- (9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazol-3-yl) -12-phenyl-12H-benzo as a light emitting host material
  • An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that [4,5] thieno [2,3-a] carbazole) was used.
  • the electroluminescence (EL) characteristics of the organic electroluminescent devices prepared by Experimental Example 1 and Comparative Examples 1 to 5 were measured by PR-650 of photoresearch by applying a forward bias DC voltage.
  • the T95 life was measured by the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.
  • the organic light emitting display device manufactured according to Example 1 of the present invention is described as Examples 1 to 103.
  • the compounds of the present invention than Comparative Examples 1 to 5 were found to exhibit mostly low driving voltage, high efficiency and high lifetime.
  • the compounds of the present invention including heterocyclic groups at the positions of R 1 to R 4 and R 11 to R 14 of the core showed relatively high driving voltages, low efficiency, and low life, as in Comparative Examples 2 and 3.
  • heterocyclic group is connected at R 1 ⁇ R 4 and R 11 ⁇ R 14 , it has relatively small band gap, HOMO increases, hole mobility decreases, driving voltage increases, efficiency and lifespan It seems to be lowering.
  • Comparative Examples 4 and 5 which are compounds substituted with hydrogen at the positions of R 1 to R 4 and R 11 to R 14 of the core, it was confirmed that the lifespan was lower than that of the compound of the present invention.
  • 2-TNATA was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and NPD was then vacuum deposited to a thickness of 20 nm on the film to form a hole transport layer.
  • the compound of the present invention (3-28 to 3-51, 4-28 to 4-51, 6-1 to 6-48, 7-1 to 7-48) as the host material on the hole transport layer, piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] as a dopant material and then doped at 95: 5 weight to deposit a 30 nm thick light emitting layer, and then vacuum BAlq to 10 nm thick The vapor deposition was performed to form a hole blocking layer, and Alq 3 was formed to a thickness of 40 nm to form an electron injection layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form an Al / LiF cathode, thereby manufacturing an organic EL device.
  • An organic electroluminescent device was manufactured according to the same method as Experimental Example 2, except that Comparative Compound 1 (4,4'-di (9H-carbazol-9-yl) -1,1'-biphenyl) was used as a light emitting host material. Produced.
  • Comparative compound 2 (9- (9- (4,6-diphenylpyrimidin-2-yl) -9H-carbazol-3-yl) -12-phenyl-12H-benzo [4,5] thieno [3, as a luminescent host material
  • An organic electroluminescent device was manufactured in the same manner as in Experiment 2, except that 2-a] carbazole) was used.
  • Comparative compound 3 (3- (9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazol-3-yl) -12-phenyl-12H-benzo [3] as a light emitting host material [ 4,5] thieno [2,3-a] carbazole), except that the organic electroluminescent device was manufactured in the same manner as in Experiment 2.
  • Comparative Compound 4 (12- (5-phenylpyrimidin-2-yl) -12H-benzo [4,5] thieno [3,2-a] carbazole) was used as a light emitting host material.
  • An organic electroluminescent device was manufactured by the method.
  • the electroluminescent (EL) characteristics of the organic electroluminescent devices prepared by Experimental Example 2 and Comparative Examples 6 to 10 were measured by PR-650 of photoresearch by applying a forward bias DC voltage.
  • the T95 life was measured by the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.
  • the organic light emitting display device manufactured according to Experimental Example 2 of the present invention is described as Examples 119 to 262.
  • Comparative Compound 4 and Comparative Compound 5 showed a higher lifespan than Comparative Compound 2 and Comparative Compound 3 when used as a phosphorescent green host, but were lower than Comparative Compound 2 and Comparative Compound 3, as can be seen from the above table used as a phosphorescent red host. It was confirmed that the efficiency and low life.
  • the compound of the present invention (5-1 to 5-7, 5-11 to 5-14 , 5-17 to 5-31, 5-33 to 5-35) were vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and then Alq 3 was formed to a thickness of 40 nm to form an electron injection layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode to prepare an organic light emitting device.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example 3, except that Comparative Compound 8 (N- (9,9-dimethyl-9H-fluoren-2-yl) -N, 12-diphenyl-12H- was used instead of the compound of the present invention.
  • a hole transport layer was formed using benzo [4,5] thieno [3,2-a] carbazol-9-amine).
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example 3, except that the comparative compound 9 (N, N-di ([1,1'-biphenyl] -4-yl) -12-phenyl-12H- was used instead of the compound of the present invention.
  • a hole transport layer was formed using benzo [4,5] thieno [2,3-a] carbazol-8-amine).
  • the electroluminescent (EL) characteristics of the organic light emitting diodes prepared by Experimental Example 3 and Comparative Example were measured by applying a positive bias DC voltage to the photoresearch company PR-650. At this time, the T95 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance. In the table below, the organic light emitting display device manufactured according to Experimental Example 3 was described as Examples 262 to 290.
  • the compounds of the present invention show a lower driving voltage and a higher efficiency, in particular, a higher lifetime than those of Comparative Examples 11 to 14.
  • One of R 1 to R 4 and R 11 to R 14 positions in the core is substituted with an aryl group, and in the case of a compound containing an arylamine group in the other, HOMO levels are lowered, thereby transferring holes to the light emitting layer more easily. As a result, it is judged that the service life is long.
  • 2-TNATA was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and then 4,4-bis [N- (1-naphthyl) on the hole injection layer.
  • -N-phenylamino] biphenyl (Comparative Compound 6) was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
  • the compound of the present invention (5-1 to 5-7, 5-11 to 5-14, 5-17 to 5-31, 5-33 to 5-35, 5-47 to 5-51) was 20 nm thick. Vacuum deposition to form a light emitting auxiliary layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium
  • a 30 nm thick light emitting layer was deposited by doping at 95: 5 weight with a dopant material.
  • BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a holdoff layer, and then Alq 3 was formed to a thickness of 40 nm to form an electron injection layer.
  • LiF an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting device.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example 4, except that Comparative Compound 7 (N, N, 12-triphenyl-12H-benzo [4,5] thieno [3,2-a] carbazol- was used instead of the compound of the present invention. 9-amine) to form a light emitting auxiliary layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example 4, except that Comparative Compound 8 (N- (9,9-dimethyl-9H-fluoren-2-yl) -N, 12-diphenyl-12H- was used instead of the compound of the present invention.
  • a light emitting auxiliary layer was formed using benzo [4,5] thieno [3,2-a] carbazol-9-amine).
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example 3, except that the comparative compound 9 (N, N-di ([1,1'-biphenyl] -4-yl) -12-phenyl-12H- was used instead of the compound of the present invention.
  • a light emitting auxiliary layer was formed using benzo [4,5] thieno [2,3-a] carbazol-8-amine).
  • the electroluminescent (EL) characteristics of the organic electroluminescent devices manufactured by Experimental Example 4 and Comparative Example were measured by applying a forward bias DC voltage to the photoresearch company PR-650, as shown in the following table. At this time, the T95 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.
  • the organic electric device manufactured by Experimental Example 4 of the present invention is represented by Examples 291 to 324 in Table 7 below.
  • the efficiency and the lifespan were increased compared to those of the comparative compound used as the light emitting auxiliary layer.
  • the hole is formed between the HOMO level of Comparative Compound 6 used as the hole transport layer and the HOMO level of the light emitting layer.
  • a light emitting auxiliary layer having a HOMO level that can deliver faster than can be determined to show a high efficiency and a high lifetime.

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Abstract

La présente invention concerne un nouveau composé comprenant un hétérocycle à cinq atomes qui peut augmenter l'efficacité électroluminescente, la stabilité et la durée de vie d'un dispositif, ainsi qu'un dispositif électronique organique et un appareil électronique le comprenant.
PCT/KR2012/011234 2012-01-18 2012-12-21 Composé pour dispositif électronique organique, dispositif électronique organique et appareil électronique le comprenant Ceased WO2013108997A1 (fr)

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CN107428769A (zh) * 2015-08-27 2017-12-01 株式会社Lg化学 杂环化合物及包含其的有机发光元件
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KR102050501B1 (ko) * 2016-03-30 2019-11-29 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20170112874A (ko) * 2016-03-30 2017-10-12 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
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