WO2019045405A1 - Composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

Composé hétérocyclique et élément électroluminescent organique l'utilisant Download PDF

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WO2019045405A1
WO2019045405A1 PCT/KR2018/009897 KR2018009897W WO2019045405A1 WO 2019045405 A1 WO2019045405 A1 WO 2019045405A1 KR 2018009897 W KR2018009897 W KR 2018009897W WO 2019045405 A1 WO2019045405 A1 WO 2019045405A1
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서상덕
홍성길
김성소
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주식회사 엘지화학
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a heterocyclic compound represented by the general formula (1) and an organic light emitting device including the same.
  • the organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule.
  • the principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between an anode and a cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer are recombined in the light emitting layer to form a molecular exiton, which is an electron-hole pair, and the exciton falls back to a ground state where energy is lowered again.
  • An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
  • the light emitting layer is composed of only the light emitting material or has a structure including a very small amount of the light emitting material (dopant).
  • a material containing a light emitting material is referred to as a host material or a matrix material, and a light emitting material is referred to as a dopant or guest material.
  • the light emitting material improves the efficiency of the OLED by generating more photons from the excitons, and has a variety of colors for each light emitting material, which plays an important role in controlling the color of the OLED.
  • An object of the present invention is to provide an organic light emitting device having a low driving voltage, high efficiency, and good lifetime characteristics by using the heterocyclic compound represented by the formula (1) in an organic light emitting device.
  • One embodiment of the present invention provides a heterocyclic compound represented by the following general formula (1).
  • L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar is a substituted or unsubstituted nitrogen heteroaryl group
  • X1 and X2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group; Or an aryl group,
  • S1 to S3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; -SiRaRbRc; -ORd; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -NReRf, wherein Ra to Rf are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a is an integer of 0 to 6, and when a is 2 or more, S1 is the same or different from each other,
  • b is an integer of 0 to 4, and when b is 2 or more, S2 is the same or different from each other,
  • substituted or unsubstituted means deuterium; A halogen group; A nitrile group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; A heteroaryl group; -OR 25 ; -NR 26 R 27 ; And -SiR 28 R 29 from the group consisting of R 30 with one or more substituents selected, or substituted or unsubstituted, and a group of two or more of the above-exemplified substituents linked substituent means a substituted or unsubstituted, R 25 to R 30 is Each independently of the other hydrogen; heavy hydrogen; An alkyl group; Or an aryl group.
  • An embodiment of the present invention is also an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer is represented by Formula 1 A heterocyclic compound, and a heterocyclic compound.
  • the heterocyclic compound of the present invention can be used as a host material for a red light emitting layer in an organic light emitting device.
  • a low driving voltage, high efficiency, and / or high longevity can be obtained.
  • Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, an organic layer 10 and a cathode 9.
  • FIG. 2 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 3, a hole transporting layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transporting layer 7, And a cathode (9).
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec- n-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, But are not limited to these.
  • the cycloalkyl group is not particularly limited, but the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like.
  • the alkoxy group is a group represented by -OR 31
  • R 31 is an alkyl group.
  • the number of carbon atoms of R 31 is 1 to 40, 1 to 30, 1 to 20, 1 to 10, preferably 1 to 6.
  • Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an isoamyloxy group and a hexyloxy group.
  • an alkenyl group represents a straight chain or branched chain unsaturated hydrocarbon group, and may be linear or branched.
  • the number of carbon atoms is not particularly limited, but is 2 to 30 or 2 to 20.
  • Specific examples of the alkenyl group include, but are not limited to, ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, t-butenyl, n-pentenyl and n-hexenyl.
  • the aryl group means a monovalent group of a monovalent aromatic hydrocarbon or aromatic hydrocarbon derivative.
  • aromatic hydrocarbon means a compound including a ring in which pi electrons are completely conjugated and planar
  • a group derived from an aromatic hydrocarbon means a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed to an aromatic hydrocarbon .
  • an aryl group is intended to include monovalent groups in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are linked to each other.
  • the number of carbon atoms of the aryl group is not particularly limited, but is 6 to 60, 6 to 40, preferably 6 to 30.
  • the aryl group may be monocyclic or polycyclic.
  • the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a quaterphenyl group.
  • polycyclic aryl group examples include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a tetracenyl group, a klycenyl group, a fluorenyl group, An acenaphthyl group, a benzofluorenyl group, and the like, but are not limited thereto.
  • the substituted fluorenyl group when the fluorenyl group can be substituted, includes all of the compounds in which the substituents on the pentagonal ring of the fluorene are spiro bonded to each other to form an aromatic hydrocarbon ring.
  • Such substituted fluorenyl groups include 9,9'-spirobifluorene, spiro [cyclopentane-1,9'-fluorene], spiro [benzo [c] fluorene-7,9-fluorene] But is not limited thereto.
  • the heteroaryl group means a monovalent aromatic heterocycle.
  • the aromatic heterocyclic ring means a monovalent group of an aromatic ring or a derivative of an aromatic ring, and includes a hetero atom containing one or more of N, O and S in the ring.
  • the derivative of the aromatic ring includes both structures in which an aromatic ring or an aliphatic ring is condensed to an aromatic ring.
  • the number of carbon atoms of the heteroaryl group is not particularly limited, but is 2 to 60, 2 to 40, preferably 2 to 30.
  • examples of the heteroaryl group include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, , Pyrimidinyl group, triazinyl group, triazolyl group, acridinyl group, carbovinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a
  • a nitrogen-containing heteroaryl group means a heteroaryl group containing at least one N in the ring.
  • the arylamine group is a substituted or unsubstituted monoarylamine group; Or a substituted or unsubstituted diarylamine group.
  • the aryl group in the arylamine group may be described with respect to the aryl group described above.
  • arylamine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methylnaphthylamine, 2-methylbiphenylamine, 9-methyl anthracenylamine, di But are not limited to, phenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, and the like.
  • an arylalkyl group In the present specification, an arylalkyl group; And the aryl group in the arylalkenyl group, the description of the aryl group described above can be applied.
  • the description of the aryl group can be applied except that the arylene group is divalent.
  • heteroaryl group is applicable except that the heteroarylene group is divalent.
  • Quot refers to a moiety that is connected to another substituent.
  • the heterocyclic compound of the formula (1) is a bipolar substance in which the benzocarbazole in which the formula (D) is condensed acts as an electron donor, and Ar is an electron acceptor.
  • the triplet position may be located in the electron donor portion or the electron acceptor portion, depending on the configuration of each portion. In this case, when the triplet position is located at the portion of the electron acceptor, unstable double-hole bipolar lon is likely to be formed due to interaction with the hole-polaron, resulting in degradation of the lifetime of the device.
  • the triplet position is located in the electron donor region, it is difficult to oxidize and a higher lifetime can be expected.
  • the heterocyclic compound represented by the general formula (1) of the present invention has a structure in which -L-Ar is substituted by a hydrocarbon ring not containing nitrogen, since the nitrogen heterocycle (substituent Ar) is substituted for the core (benzocarbazole in which the D is condensed) which is more suitable as a host of the red light emitting layer of the organic electroluminescent device than the compound formed.
  • the formula (1) is represented by any one of the following formulas (2) to (4).
  • c is an integer of 0 to 2, and when c is 2, S3 is the same or different.
  • X1 and X2 are independently selected from the group consisting of hydrogen; An alkyl group of C1-C10; Or an aryl group of C6-C25.
  • X1 and X2 are each an alkyl group.
  • X1 and X2 are each a methyl group.
  • X1 and X2 are each an aryl group.
  • X1 and X2 are each a phenyl group.
  • S1 is hydrogen
  • S2 is hydrogen
  • S3 is hydrogen
  • a is zero.
  • b is zero.
  • c is zero.
  • a substituent of a certain structure when a substituent of a certain structure is represented by - (M) m, it means that m may be substituted into the structure thereof. Where m is 0, which means that M is not substituted into the structure. Also, even if M is hydrogen and m is 0, this does not mean that hydrogen is not bonded to the structure, and only the substituent represented by M is not substituted into the structure.
  • L is a direct bond; An arylene group substituted or unsubstituted with R 1 ; Or a heteroarylene group substituted or unsubstituted with R < 2 & gt ;.
  • R 1 and R 2 are the same or different and are each independently selected from the group consisting of deuterium; A halogen group; A nitrile group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; A heteroaryl group; -OR 25 ; -NR 26 R 27 ; And -SiR 28 R 29 from the group consisting of R 30 with one or more substituents selected, or substituted or unsubstituted, and a group of two or more of the above-exemplified substituents linked substituent means a substituted or unsubstituted, R 25 to R 30 is Each independently of the other hydrogen; heavy hydrogen; An alkyl group; Or an aryl group.
  • L is a direct bond; A substituted or unsubstituted C6-C36 arylene group; Or a substituted or unsubstituted C2-C36 heteroarylene group.
  • L is a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group.
  • L is a direct bond; A substituted or unsubstituted C6-C25 arylene group; Or a substituted or unsubstituted C2-C25 heteroarylene group.
  • L is a direct bond; A substituted or unsubstituted C6-C18 arylene group; Or a substituted or unsubstituted C2-C20 heteroarylene group.
  • L is a substituted or unsubstituted phenylene group; A substituted or unsubstituted divalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent quaterphenyl group; A substituted or unsubstituted divalent naphthalene group; A substituted or unsubstituted divalent anthracene group; A substituted or unsubstituted divalent phenanthrene group; A substituted or unsubstituted divalent triphenylene group; A substituted or unsubstituted divalent pyylene group; A substituted or unsubstituted divalent fluorene group; A substituted or unsubstituted divalent dibenzofurane group; Or a substituted or unsubstituted divalent dibenzothiophene group.
  • L is a direct bond; A phenylene group; A divalent naphthalene group; Or a divalent dibenzofurane group.
  • Ar is a nitrogen heteroaryl group substituted or unsubstituted with R < 3 >.
  • R < 3 &gt is deuterium; A halogen group; An alkyl group; A cycloalkyl group; An aryl group; And a heteroaryl group, or a group to which at least two of the above exemplified substituents are connected.
  • R < 3 &gt is deuterium; A halogen group; An alkyl group of C1-C10; A C3-C10 cycloalkyl group; An aryl group of C6-C25; And a heteroaryl group of C2-C25, or a group to which at least two of the above-exemplified substituents are connected.
  • R 3 is a phenyl group, a naphthyl group, a biphenyl group, a dimethylfluorenyl group, a carbazole group substituted or unsubstituted with a phenyl group, a dibenzothiophenyl group, or a dibenzofuranyl group.
  • Ar is a nitrogen-containing heteroaryl group substituted with R 3 .
  • Ar is a substituted or unsubstituted nitrogen-containing heteroaryl group of C2-C45.
  • Ar is a substituted or unsubstituted nitrogen-containing heteroaryl group of C2-C30.
  • Ar is a substituted or unsubstituted nitrogen heteroaryl group containing at least two N atoms.
  • Ar is a monocyclic or polycyclic nitrogen heteroaryl group containing a 6-membered ring containing 2 or more N and being substituted or unsubstituted.
  • Ar is a substituted or unsubstituted monocyclic or polycyclic nitrogen heteroaryl group containing a 6-membered aromatic ring containing 2 or more Ns.
  • Ar is a substituted or unsubstituted 1 to 5-membered nitrogen-containing heteroaryl group containing 6-membered rings containing 2 or more Ns.
  • Ar is a substituted or unsubstituted 1 to 3-membered nitrogen-containing heteroaryl group containing 6-membered rings containing 2 or more Ns.
  • Ar is a substituted or unsubstituted pyrimidinyl group; A substituted or unsubstituted diazinyl group; A substituted or unsubstituted thiazinyl group; A substituted or unsubstituted diazanaphthyl group; A substituted or unsubstituted naphthyridinyl group; A substituted or unsubstituted quinoxalinyl group; A substituted or unsubstituted benzoquinoxalinyl group; A substituted or unsubstituted quinazolinyl group; A substituted or unsubstituted benzoquinazolinyl group; Or a substituted or unsubstituted phenazinyl group.
  • Ar is a quinazolinyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A benzoquinazolinyl group substituted or unsubstituted with an aryl group or a heteroaryl group; A triazinyl group substituted or unsubstituted with an aryl group or a heteroaryl group; Or a diaryl group substituted or unsubstituted with an aryl group or a heteroaryl group.
  • Ar is represented by the following formula (11).
  • Y1 is N or CR 11
  • Y2 is N or CR 12
  • Y3 is N or CR 13
  • Y4 is N or CR 14
  • Y5 is N or CR 15, at least two of Y1 to Y5 is N, and ,
  • R 11 to R 15 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; A cycloalkyl group; A nitrile group; An alkenyl group; An alkoxy group; An arylamine group; Arylalkyl groups; An arylalkenyl group; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group, Two adjacent groups of R 11 to R 15 are bonded to each other to form a ring substituted or unsubstituted with R 16 ,
  • R 16 is deuterium; A halogen group; An alkyl group; A cycloalkyl group; A nitrile group; An alkenyl group; An alkoxy group; An arylamine group; Arylalkyl groups; An arylalkenyl group; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • adjacent group may mean a substituent in which the substituent is substituted with an atom directly connected to the substituted atom, and a substituent which is stereostatically closest to the substituent.
  • the meaning of forming a ring by bonding to adjacent groups means that the adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle or a substituted Or an unsubstituted aromatic heterocycle.
  • Y1 is N.
  • 2 to 4 of Y1 to Y5 are N.
  • the formula (11) is represented by the following formula (12) or (13).
  • two adjacent groups among Y 2 to Y 5 are CR 17 and CR 18 , and R 17 and R 18 combine with each other to form an aromatic hydrocarbon ring, and two of Y 2 to Y 5 other than CR 17 and CR 18
  • One of the groups is N and the other is CR 19 ;
  • R 19 is hydrogen; heavy hydrogen; A halogen group; An alkyl group; A cycloalkyl group; A nitrile group; An alkenyl group; An alkoxy group; An arylamine group; Arylalkyl groups; An arylalkenyl group; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group,
  • Y2 is CR 20
  • Y4 is a CR 21
  • R 20 and R 21 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; A cycloalkyl group; A nitrile group; An alkenyl group; An alkoxy group; An arylamine group; Arylalkyl groups; An arylalkenyl group; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • R 17 and R 18 combine with each other to form a C6-C18 aromatic hydrocarbon ring.
  • R 17 and R 18 combine with each other to form a C6-C14 aromatic hydrocarbon ring.
  • R 17 and R 18 are bonded to each other to form a benzene ring or a naphthalene ring.
  • R < 19 &gt is deuterium; A halogen group; An alkyl group; A cycloalkyl group; A nitrile group; An alkenyl group; An alkoxy group; An arylamine group; Arylalkyl groups; An arylalkenyl group; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • At least one of R 20 and R 21 is deuterium; A halogen group; An alkyl group; A cycloalkyl group; A nitrile group; An alkenyl group; An alkoxy group; An arylamine group; Arylalkyl groups; An arylalkenyl group; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • Ar of formula (1) when Ar of formula (1) is a substituted nitrogen-containing heterocyclic ring, it is more suitable as a red host of an organic light emitting device.
  • Ar may be selected from among the following groups.
  • Each of the structures being independently selected from the group consisting of deuterium; A halogen group; An alkyl group; A cycloalkyl group; A nitrile group; An alkenyl group; An alkoxy group; An arylamine group; Arylalkyl groups; An arylalkenyl group; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • the structures may be the same or different and each independently substituted or unsubstituted with a phenyl group, a naphthyl group, a biphenyl group, a carbazole group substituted with an aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group .
  • the heterocyclic compound represented by Formula 1 is any one selected from the following compounds.
  • the above-mentioned heterocyclic compound of formula (1) can be formed by a reaction to bond N to the -L-Ar group of the core of the compound of the present invention
  • X3 is a halogen group
  • L, Ar, X1 and X2 have the same meanings as defined in the above formula (1).
  • the present invention provides an organic light emitting device comprising the heterocyclic compound represented by Formula 1.
  • an organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, And a heterocyclic compound to be displayed.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, And a heterocyclic compound represented by the general formula (1).
  • the organic layer includes a light-emitting layer, and the light-emitting layer includes a heterocyclic compound represented by the general formula (1).
  • the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a heterocyclic compound represented by the above formula (1).
  • the organic layer includes an electron blocking layer, and the electron blocking layer includes a heterocyclic compound represented by the general formula (1).
  • the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, And a heterocyclic compound represented by the above formula (1).
  • the organic material layer includes a light emitting layer and an electron transporting layer
  • the electron transporting layer includes a heterocyclic compound represented by the above formula (1).
  • at least one of the two or more organic layers includes at least one organic compound selected from the group consisting of a heterocycle represented by Formula 1, ≪ / RTI >
  • the two or more organic layers may be selected from the group consisting of an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and an electron injecting layer, and a hole blocking layer.
  • the organic material layer includes two or more hole injection layers.
  • the two or more hole injection layers may be formed of the same or different materials.
  • the organic material layer includes two or more electron transporting layers, and at least one of the electron transporting layers of two or more layers includes a heterocyclic compound represented by the above formula (1).
  • the heterocyclic compound represented by Formula 1 may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.
  • the materials other than the heterocyclic compound of Formula 1 may be the same or different from each other can do.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is a cathode.
  • FIGS. 1-10 the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.
  • Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, an organic layer 10 and a cathode 9.
  • the heterocyclic compound represented by Formula 1 may be included in the organic material layer 10.
  • FIG. 2 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 3, a hole transporting layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transporting layer 7, And a cathode (9).
  • the heterocyclic compound may be included in the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the electron transporting layer, or the electron injecting layer.
  • the organic light emitting device of the present invention can be manufactured by materials and methods known in the art except that one or more of the organic layers include the compound of the present invention, i.e., the heterocyclic compound represented by the above formula (1).
  • the organic layers may be formed of the same material or different materials.
  • the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode
  • an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon depositing a material usable as a cathode thereon.
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting material is a layer for injecting holes from the electrode.
  • the hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material.
  • a compound which prevents the migration of excited excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the electron blocking layer is a light emitting layer that prevents exciter electrons from flowing into the anode and controls the performance of the entire device by controlling the flow of holes flowing into the light emitting layer.
  • the electron blocking material is preferably a compound having an ability to prevent the inflow of electrons from the light emitting layer to the anode and control the flow of holes injected into the light emitting layer or the light emitting material.
  • an arylamine-based organic material may be used as the electron blocking layer, but the present invention is not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Benzoxazole, benzothiazole and benzimidazole compounds; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic compound.
  • Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds and fluoranthene compounds.
  • Examples of heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material of the light emitting layer include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivative a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group may be used, such as pyrene, anthracene, klysene, and peripherrhene having an arylamine group.
  • As the styrylamine compound a compound in which substituted or unsubstituted arylamine is substituted with at least one aryl vinyl group can be used.
  • styrylamine compound examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • metal complex an iridium complex, a platinum complex, or the like can be used, but it is not limited thereto.
  • the hole blocking layer is a layer which blocks the flow of holes from the light emitting layer into the cathode and adjusts the performance of the entire device by controlling electrons flowing into the light emitting layer.
  • the hole blocking material a compound having an ability to prevent the inflow of holes from the light emitting layer to the cathode and to control electrons injected into the light emitting layer or the light emitting material is preferable.
  • the hole blocking material an appropriate material may be used depending on the constitution of the organic material layer used in the device.
  • the hole blocking layer is disposed between the light emitting layer and the cathode, and is preferably provided directly in contact with the light emitting layer.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emission layer.
  • the electron transporting material a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable.
  • the electron transporting material include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complex, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • the negative electrode material comprises a material having a low work function; And an aluminum layer or a silver layer may be used. Examples of the material having the low work function include cesium, barium, calcium, ytterbium, and samarium.
  • An aluminum layer or a silver layer may be formed on the layer after forming the layer with the material.
  • the electron injection layer is a layer for injecting electrons received from the electrode into the light emitting layer.
  • the electron injecting material has an ability to transport electrons, has an electron injecting effect from the cathode, an excellent electron injecting effect to the emitting layer or the light emitting material, prevents migration of the excitons produced in the emitting layer into the hole injecting layer, Further, it is preferable to use a compound having excellent ability to form a thin film.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • a thin glass substrate coated with ITO (Indium Tin Oxide) at a thickness of 1,400 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered by a filter of Millipore Co. was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • HI-A and hexaazatriphenylene were sequentially deposited by thermal vacuum deposition to a thickness of 800 ANGSTROM and 50 ANGSTROM, respectively, on the thus prepared ITO transparent electrode to form a hole injection layer.
  • the following HT-A was vacuum-deposited as a hole transporting layer to a thickness of 800 ⁇
  • EB-A as an electron blocking layer was thermally vacuum deposited to a thickness of 600 ⁇ .
  • host RH-A and dopant RD of 2 wt% were vacuum deposited as a light emitting layer to a thickness of 400 ANGSTROM.
  • ET-A and Liq were thermally vacuum deposited at a weight ratio of 1: 1 to a thickness of 360 ANGSTROM as an electron transporting and injecting layer, followed by vacuum deposition of Liq to a thickness of 5 ANGSTROM.
  • Magnesium and silver were sequentially deposited on the electron injection layer at a weight ratio of 10: 1 to a thickness of 220 ⁇ and aluminum to a thickness of 1000 to form a cathode, thereby preparing an organic light emitting device.
  • the organic light-emitting devices of the element examples 1 to 9 and the comparative examples 2 to 5 were fabricated by the same method as in the above-mentioned ⁇ Comparative example 1> except that the RH-A was used in the above-mentioned ⁇ Comparative example 1> Respectively.
  • the current, voltage, efficiency and lifetime of the fabricated organic light emitting device were measured. The results are shown in Table 1 below. At this time, the voltage and the efficiency were measured by applying a current density of 10 mA / cm 2 , and the LT98 means the time until the initial luminance decreased to 98% at a current density of 20 mA / cm 2 .
  • the compound of formula (D) is represented by the structure of formula (1) of the present invention, and 1,14-dihydrobenzo [h] indeno [2,1-a] carbazole, 5,14-hydrobenzo [h] indeno [ , 2-a] carbazole or 7,14-hydrobenzo [b] indeno [2,1-g] carbazole in the form of a condensation product, .

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  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention concerne un composé hétérocyclique représenté par la formule chimique 1 et un élément électroluminescent organique le comprenant.
PCT/KR2018/009897 2017-08-28 2018-08-28 Composé hétérocyclique et élément électroluminescent organique l'utilisant WO2019045405A1 (fr)

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