WO2016105123A2 - Composé organique et dispositif électroluminescent organique comprenant un tel composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant un tel composé Download PDF

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WO2016105123A2
WO2016105123A2 PCT/KR2015/014185 KR2015014185W WO2016105123A2 WO 2016105123 A2 WO2016105123 A2 WO 2016105123A2 KR 2015014185 W KR2015014185 W KR 2015014185W WO 2016105123 A2 WO2016105123 A2 WO 2016105123A2
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group
aryl
compound
formula
groups
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WO2016105123A3 (fr
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배형찬
김영배
김성무
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주식회사 두산
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • 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
    • C07D403/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting material may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, it can be divided into yellow and orange light emitting materials required to achieve a better natural color.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically improve luminous efficiency up to four times compared to fluorescence, attention is being paid not only to phosphorescent dopants but also to phosphorescent host materials.
  • NPB, BCP, Alq 3 and the like are widely known as materials used for the hole blocking layer and the electron transporting layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials.
  • phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which are blue and green. It is used as a red dopant material.
  • CBP has shown excellent properties as a phosphorescent host material.
  • the conventional light emitting materials are good in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, and thus they are not satisfactory in terms of lifespan in the organic EL device. Therefore, there is a demand for the development of an organic EL device including a light emitting material having excellent performance.
  • the device in order to realize the practical use and characteristics of the organic electroluminescent device, not only the device is composed of the organic material layer having the multilayer structure as described above, but also the material of the device, in particular, the hole transport material should have thermal and electrical stable properties. Because, when a voltage is applied to the device, molecules with low thermal stability due to heat generated by the device have low crystal stability, resulting in rearrangement, and eventually crystallization occurs locally, resulting in an inhomogeneous part. This is because the concentration on the part causes degradation and destruction of the device.
  • conventionally used hole transport materials include m-MTDATA [4, 4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) -triphenylamine, 2-TNATA. [4, 4 ', 4-?-Tris (N- (naphthylene-2-yl) -N-phenylamino) -triphenylamine], TPD [N, N'-diphenyl-N, N'-di ( 3-methylphenyl) -4, 4'-diaminobiphenyl] and NPB [N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine].
  • m-MTDATA and 2-TNATA have a low glass transition temperature (Tg) of 78 ° C. and 108 ° C., respectively, and have a problem in realizing full color because many problems occur during mass production.
  • TPD and NPB also has a fatal disadvantage that the glass transition temperature (Tg) as low as 60 °C and 96 °C, respectively, shorten the life of the device for the same reason. Accordingly, there is a demand for the development of an organic electroluminescent device capable of improving thermal stability, having excellent hole transporting ability, and improving the luminous efficiency and power efficiency of the organic electroluminescent device.
  • An object of the present invention is to provide a compound which is excellent in electron blocking ability, hole transporting ability, and the like, which can be used as a light emitting layer material, a light emitting auxiliary layer material, and a hole transporting layer material.
  • Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, a high luminous efficiency, and an improved lifetime including the novel compound described above.
  • the present invention provides a compound represented by Formula 1:
  • a is an integer from 0 to 5;
  • b is an integer from 0 to 3;
  • c is an integer from 0 to 4.
  • R 1 to R 4 are the same as or different from each other, and each independently deuterium, a halogen, a cyano group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, and a nuclear atom having 3 to 40 heterocycloalkyl groups , C 6 ⁇ C 60 aryl group, nuclear atom 5 ⁇ 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group , C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine It may be selected from the group consisting of an oxide group and a C 6 ⁇ C 60 arylamine group, or may be combined with an adjacent substituent to form
  • At least one of R 1 to R 4 is a substituent represented by Formula 2;
  • L 1 is a single bond, or is C 6 ⁇ C 60 arylene group and a nucleus atoms is selected from the group consisting of a hetero arylene of 5 to 60;
  • Ar 1 and and Ar 2 are the same or different and are each independently a C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ C 60 of It may be selected from the group consisting of an arylamine group, or Ar 1 and Ar 2 may be bonded to each other to form a ring,
  • the silyl group, the arylsilyl group, the alkyl boron group, the aryl boron group, the aryl phosphine group, the aryl phosphine oxide group, the arylamine group, and the arylene group and heteroarylene group of L 1 are deuterium, halogen, cyano, C 1- C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.
  • the organic material layer of one or more layers including the compound represented by Chemical Formula 1 is selected from the group consisting of a hole transporting layer, a light emitting auxiliary layer, and a light emitting layer.
  • the organic electroluminescent device of the present invention includes a compound having excellent heat resistance, light emitting ability, hole transporting ability, and the like in at least one or more organic material layers, aspects such as light emission performance, driving voltage, lifetime, efficiency, and the like can be greatly improved. Furthermore, the present invention can be effectively applied to a full color display panel or the like.
  • the compound according to the present invention is aryl at any one of the phenyl group moiety, one of both benzene moieties of carbazole, and the nitrogen moiety of carbazole, on the basic skeleton of the phenylcarbazole moiety having a phenyl group introduced at position 1 of the carbazole.
  • a structure in which an amine group-containing substituent is introduced is represented by Chemical Formula 1.
  • the position number of carbazole can be represented as follows.
  • the compound according to the present invention a phenyl group is introduced at position 1 of the carbazole, such that the compound molecule is distorted, and thus, there is no problem of deterioration in luminescence properties due to pi-stacking. Therefore, the compound of the present invention can prevent the formation of excitation dimers (eximers), thereby improving the luminous efficiency of the OLED.
  • the compound of the present invention since the compound of the present invention has a lower deposition temperature than a carbazole compound in which a phenyl group is introduced at position 1 of the carbazole, the thermal stability of the molecule may be enhanced.
  • the light emitting layer generally includes a host and a dopant to increase color purity and luminous efficiency.
  • the host material should have a triplet energy gap of the host higher than the dopant.
  • the dopant to provide effective phosphorescence emission the lowest excited state of the host must be higher in energy than the lowest emission state of the dopant.
  • the phenylcarbazole moiety in the compound of the present invention has a wide singlet energy level and a high triplet energy level. Therefore, when the compound of the present invention is applied as a host of the light emitting layer, it can exhibit a higher energy level than the dopant, the light emitting performance of the OLED can be improved.
  • the compound of the present invention since the compound of the present invention has a high triplet energy gap as described above, it is possible to prevent the exciton generated in the light emitting layer from being diffused (moved) into the adjacent hole transport layer. Therefore, when the organic material layer (hereinafter referred to as "light emitting auxiliary layer”) is formed between the hole transport layer and the light emitting layer using the compound of the present invention, the exciton is prevented from being diffused by the compound, thus including the light emitting auxiliary layer. Unlike conventional organic electroluminescent devices that do not, substantially the number of excitons that contribute to light emission in the light emitting layer can be improved to improve the luminous efficiency of the device.
  • both the arylamine group and the carbazole group are electron donating groups (EDGs) having large electron donating properties, and are thermally stable and have excellent hole mobility. Therefore, the compound of the present invention containing an arylamine group-containing substituent and a carbazole moiety has excellent thermal stability and high hole mobility, so that the device performance can be improved when used as a hole transporting material of an OLED. Can be.
  • EDGs electron donating groups
  • the compound represented by the general formula (1) of the present invention by introducing a variety of substituents in the basic skeleton, the molecular weight of the compound is significantly increased, and thus the glass transition temperature is improved according to the conventional CBP (4,4-dicarbazolybiphenyl) Higher thermal stability.
  • the compound of the present invention is also effective in suppressing crystallization of the organic material layer.
  • the compound of the present invention when applied to an organic material layer material of the organic EL device, preferably, an emission layer material, a hole transport layer material, or an emission auxiliary layer material, the performance and lifespan characteristics of the organic EL device may be greatly improved. . As a result, the organic EL device may maximize the performance of the full color organic light emitting panel.
  • R 1 when a is 0, it means that hydrogen is not substituted with a substituent R 1 , and when a is an integer of 1 to 5, R 1 is as defined in Formula 1 above.
  • R 2 when b is 0, it means that hydrogen is not substituted with a substituent R 2 , and when b is an integer of 1 to 3, R 2 is as defined in the formula (1).
  • R 3 when c is 0, it means that hydrogen is not substituted with a substituent R 3 , when c is an integer of 1 to 4, R 3 is as defined in the formula (1).
  • R 1 is a plurality, these are the same or different, and, if R 2 is plural, if they are the same or different and, R 3 are each other plurality, which are the same or different from each other.
  • R 1 to R 4 are the same as or different from each other, and each independently deuterium, a halogen, a cyano group, a C 1 to C 20 alkyl group, a C 3 to C 20 cycloalkyl group, and a nuclear atom having 3 to 20 heterocyclo Alkyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 1 ⁇ C 20 alkyloxy group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 20 alkylsilyl group, C 6 ⁇ C 40 aryl silyl group, C 1 ⁇ C 20 group of an alkyl boron, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine It is preferably selected from the group consisting of a pin oxide group and an arylamine group of C 6 to C 40 .
  • R 1 -R 2 , R 2 -R 3 , R 3 -R 4 , and / or R 4 -R 1 are bonded to each other to contain a condensed aromatic ring or a heteroatom selected from N, P and S. Condensed heteroaromatic rings can be formed.
  • R 1 to R 4 are the same as or different from each other, and are each independently composed of a C 6 ⁇ C 40 aryl group, a heteroaryl group of 5 to 40 nuclear atoms and an arylamine group of C 6 ⁇ C 40 Can be selected from the group.
  • R 1 to R 4 is a substituent represented by the formula (2).
  • L 1 is a single bond, or C 6 ⁇ C 20 It is preferably selected from the group consisting of an arylene group, and a heteroarylene group having 5 to 40 nuclear atoms.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently C 1 ⁇ C 20 Alkyl group, C 6 ⁇ C 40 An aryl group, and a nuclear atom of 5 to 40 heteroaryl group and It is preferably selected from the group consisting of C 6 to C 40 arylamine groups, or Ar 1 and Ar 2 are preferably bonded to each other to form a condensed ring.
  • the allylene group and heteroarylene group of L 1 are deuterium, halogen, cyano, an alkyl group of C 1 to C 40 (preferably an alkyl group of C 1 to C 20 ), a cycloalkyl group of C 3 to C 40 (preferably C A cycloalkyl group having 3 to C 20 ), a heterocycloalkyl group having 3 to 40 nuclear atom
  • Examples of the substituent represented by Formula 2 include a substituent represented by the following Formula 3, but is not limited thereto.
  • Z 2 is a single bond or is selected from the group consisting of O, S, and N (R 5 ),
  • R 5 is hydrogen, deuterium (D), C 1 -C 40 alkyl group (preferably C 1 -C 20 alkyl group), C 6 -C 60 aryl group (preferably C 6 -C 30 aryl group) ), A heteroaryl group having 5 to 60 nuclear atoms (preferably a heteroaryl group having 5 to 30 nuclear atoms) and an arylamine group having a C 6 to C 60 (preferably an arylamine group having C 6 to C 30 ) Or a condensed aromatic ring or a condensed heteroaromatic ring can be combined with an adjacent substituent;
  • the aryl group, heteroaryl group and arylamine group of R 5 are each independently deuterium, halogen, cyano, C 1 ⁇ C 40 alkyl group (preferably C 1 ⁇ C 20 alkyl group), C 3 ⁇ C 40 cycloalkyl groups (preferably, C 3 ⁇ C 20 cycloalkyl group), nuclear atoms, 3 to 40 heterocycloalkyl group (preferably, the number of nuclear atoms of 3 to 20 heterocycloalkyl group of a) the, C 6 ⁇ C 60 aryl group (Preferably, an aryl group having 6 to 30 carbon atoms), a heteroaryl group having 5 to 60 nuclear atoms (preferably a heteroaryl group having 5 to 30 nuclear atoms), an alkyloxy group having 1 to 40 carbon atoms ( Preferably, C 1 ⁇ C 20 Alkyloxy group), C 6 ⁇ C 60 An aryloxy group (preferably, C 6 ⁇ C 30 An aryloxy group), C 1 ⁇ C 40
  • the compound of Formula 1 may be represented by any one of the following Formulas 4 to 7.
  • R 1 to R 4 , L 1 , Ar 1 and Ar 2 , a, b, and c are as defined in Formula 1, respectively,
  • a ' is an integer of 0-4, b' is an integer of 0-2, and c 'is an integer of 0-3.
  • Examples of the compound represented by Chemical Formula 1 include a compound represented by the following Chemical Formulas 8 to 11, but are not limited thereto.
  • R 1 to R 4 , L 1 , Ar 1 and Ar 2 , a, b, and c are as defined in Formula 1, respectively,
  • a ' is an integer of 0-4, b' is an integer of 0-2, b "is an integer of 0-1, c 'is an integer of 0-3.
  • the compound represented by Formula 1 according to the present invention may be embodied by the following compounds, but is not limited thereto.
  • unsubstituted alkyl refers to a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, non-limiting examples of which are methyl, ethyl, propyl, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • unsubstituted cycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms.
  • saturated cyclic hydrocarbon saturated cyclic hydrocarbon
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • unsubstituted heterocycloalkyl means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and at least one carbon in the ring , Preferably 1 to 3 carbons are substituted with a hetero atom such as N, O or S.
  • a hetero atom such as N, O or S.
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • unsubstituted aryl means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms, alone or in combination of two or more rings. In this case, the two or more rings may be attached in a simple or condensed form with each other. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.
  • unsubstituted heteroaryl is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably Preferably 1 to 3 carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se).
  • the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group.
  • heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.
  • unsubstituted alkyloxy refers to a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and is linear, branched or cyclic. ) May include a structure.
  • alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • unsubstituted aryloxy refers to a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms.
  • R'O- a monovalent functional group represented by R'O-, wherein R 'is aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • unsubstituted alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • unsubstituted arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms
  • Unsubstituted arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
  • unsubstituted alkyl boron group means a boron group substituted with alkyl having 1 to 40 carbon atoms
  • unsubstituted aryl boron group means a boron group substituted with aryl having 6 to 60 carbon atoms
  • An unsubstituted arylphosphine group means a phosphine group substituted with an aryl having 1 to 60 carbon atoms
  • an unsubstituted arylphosphine oxide group means a phosphine oxide group substituted with an aryl having 1 to 60 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1) (preferably, a compound represented by any one of the formulas 4 to 7).
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the organic material layers includes a compound represented by Chemical Formula 1.
  • the compound may be used alone or in combination of two or more.
  • the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer includes the compound, preferably the light emitting layer or
  • the hole transport layer may comprise the compound.
  • the compound represented by Formula 1 when included in the organic electroluminescent device as a light emitting layer material, the luminous efficiency, brightness, power efficiency, thermal stability and device life of the organic electroluminescent device can be improved.
  • the compound represented by Chemical Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and preferably, a phosphorescent host of the light emitting layer.
  • the at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer, preferably a light emitting auxiliary layer It may include a compound represented by the formula (1).
  • the efficiency light emitting efficiency and power efficiency
  • life, brightness and driving voltage of the organic light emitting device can be improved.
  • the structure of the organic EL device of the present invention is not particularly limited, and for example, the anode, one or more organic material layers and the cathode are sequentially stacked on the substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be.
  • the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate.
  • a light emission auxiliary layer may be inserted between the hole transport layer and the light emitting layer.
  • an electron injection layer may be positioned on the electron transport layer.
  • the organic electroluminescent device of the present invention is a material known in the art, except that at least one of the one or more organic material layers (eg, the light emitting layer or the light emitting auxiliary layer) is formed to include the compound represented by Chemical Formula 1 above. And by forming the organic layer and the electrode using the method.
  • the one or more organic material layers eg, the light emitting layer or the light emitting auxiliary layer
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • Examples of the substrate usable in the present invention include a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, but are not limited thereto.
  • examples of the anode material 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the material used as the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited as long as it is a conventional material known in the art.
  • Synthesis Example 2 The same procedure as in Synthesis Example 2 was carried out except that 3.0 g (6.97 mmol) of the compound Core2 synthesized in Preparation Example 2 was used instead of the compound Core1, and Inv 105 (2.7 g, yield: 54%).
  • Inv 129 (3.3 g, Yield: 60) was the same compound as in Synthesis Example 3, except that 3.0 g (6.97 mmol) of Compound Core2 of Preparation Example 2 was used instead of Compound Core1 used in Synthesis Example 3. %) was obtained.
  • a target compound Inv319 (4.8 g, 66%) was obtained in the same manner as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core4 obtained in Preparation Example 4 was used instead of Core3 used in Synthesis Example 15. Got it.
  • Inv 365 (4.4 g, 64%) was obtained by the same procedure as Synthesis Example 18, except that 3.0 g (7.58 mmol) of Core4 obtained in Preparation Example 4 was used instead of Core3 used in Synthesis Example 18. Got.
  • Inv 411 (4.5 g, 62%) was obtained by the same procedure as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core5 obtained in Preparation Example 5 was used instead of Core3 used in Synthesis Example 15. Got.
  • Inv 600 (3.1) was prepared by the same procedure as in Synthesis Example 4, except that 3g of Core 6 synthesized in ⁇ Step 4> of Preparation Example 6 and (6.41 mmol) were used instead of Core1 used in Synthesis Example 4. g, yield 68%) was obtained.
  • Inv 680 (the target compound) was prepared in the same manner as in Synthesis Example 3, except that 3.0 g (8.47 mmol) of 1-chloro-3,9-diphenyl-9H-carbazole was used instead of Core1 used in Synthesis Example 3. 4.0 g, yield 62%) was obtained.
  • a target compound C was prepared by the same procedure as in Synthesis Example 14, except that 8.5g (34.93 mmol) of 1-phenyl-9H-carbazole synthesized in ⁇ Step 1> was used instead of Core3 used in Synthesis Example 14. -1 (16 g, yield: 67%) was obtained.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then washed the substrate using UV for 5 minutes The substrate was then transferred to a vacuum depositor.
  • ITO Indium tin oxide
  • DS-H522 and DS-501 used above are products of Doosan Corporation BG, and the structures of m-MTDATA and BCP are as follows.
  • An organic EL device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of the compound Inv 1 used as the hole transport layer material in forming the hole transport layer in Example 1.
  • An organic EL device was manufactured in the same manner as in Example 1, except that NPB was used as the hole transport layer instead of the compound Inv 1 used as the hole transport layer in forming the hole transport layer.
  • the structure of the NPB used at this time is as follows.
  • Example 1 Compound Inv 1 4.2 21.2
  • Example 2 Compound Inv 13 4.3 20.1
  • Example 3 Compound Inv 37 4.1 23.3
  • Example 4 Compound Inv 49 4.0 22.6
  • Example 5 Compound Inv 70 4.5 19.5
  • Example 6 Compound Inv 87 4.7 20.1
  • Example 7 Compound Inv 89 4.3 21.6
  • Example 8 Compound Inv 91 4.5 20.5
  • Example 9 Compound Inv 93 4.9 20.0
  • Example 10 Compound Inv 105 5.0 19.6
  • Example 11 Compound Inv 129 5.2 19.8
  • Example 12 Compound Inv 141 5.1 18.6
  • Example 13 Compound Inv 183 5.0 20.0
  • Example 14 Compound Inv 221 4.3 22.5
  • Example 15 Compound Inv 227 4.5 21.2
  • Example 16 Compound Inv 233 4.4 22.3
  • Example 17 Compound Inv 254 4.9 18.5
  • Example 18 Compound Inv 273 4.8 19.9
  • Example 19 Compound Inv 3
  • the organic EL device (the organic EL device of Examples 1 to 35) using the compounds (Inv 1 to Inv 417, C-1 to C-2) according to the present invention as a hole transport layer is conventionally Compared with the organic EL element (the organic EL element of Comparative Example 1) using NPB, it was found to exhibit better performance in terms of current efficiency and driving voltage.
  • the organic EL device of Example 14 using the compound Inv 221 having a phenyl group introduced at positions 1, 3, and 6 of the carbazole, as a hole transport layer has a compound C-1 having a phenyl group introduced at position 1 of the carbazole, Compared with the organic EL devices of Examples 34 to 35 using the compound C-2 having the phenyl group introduced at the carbazole positions 1 and 4 as the hole transporting layer, it was found to have better performance in terms of current efficiency and driving voltage.
  • a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • a green organic EL device was manufactured in the same manner as in Example 36, except that each of the compounds shown in Table 2 was used instead of the compound Inv 1 used as the emission auxiliary layer material in the formation of the emission auxiliary layer in Example 36. It was.
  • a green organic electroluminescent device was manufactured in the same manner as in Example 36, except that the compound Inv 1 used in Example 36 was not used.
  • Example 36 Compound Inv 1 6.71 41.9 Example 37 Compound Inv 13 6.85 42.2 Example 38 Compound Inv 37 6.73 43.1 Example 39 Compound Inv 49 6.81 42.4 Example 40 Compound Inv 70 6.81 42.4 Example 41 Compound Inv 87 6.92 42.5 Example 42 Compound Inv 89 6.95 42.1 Example 43 Compound Inv 91 6.78 41.8 Example 44 Compound Inv 93 6.90 42.4 Example 45 Compound Inv 105 6.75 41.9 Example 46 Compound Inv 129 6.72 42.8 Example 47 Compound Inv 141 6.65 42.2 Example 48 Compound Inv 183 6.70 42.5 Example 49 Compound Inv 221 6.90 42.8 Example 50 Compound Inv 227 6.81 42.1 Example 51 Compound Inv 233 6.71 40.3 Example 52 Compound Inv 254 6.73 41.5 Example 53 Compound Inv 273 6.65 42.2 Example 54 Compound Inv 313 6.72 42.5 Example 55 Compound Inv 319 6.62 4
  • the green organic electroluminescent device (the green organic electroluminescent device of Examples 36 to 63) using the compound represented by Chemical Formula 1 according to the present invention as the light emitting auxiliary layer material, has no light emitting auxiliary layer material.
  • the conventional green organic EL device (the organic EL device of Comparative Example 2) using only CBP as the light emitting layer material, it was found that the driving voltage was similar but the light emission efficiency was improved.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • a red organic EL device was manufactured in the same manner as in Example 64, except that each of the compounds shown in Table 3 was used instead of the compound Inv 1 used as the emission auxiliary layer material in the formation of the emission auxiliary layer in Example 64. It was.
  • a red organic electroluminescent device was manufactured in the same manner as in Example 64, except that Inv-1 was not used in Example 64.
  • Example 64 Compound Inv 1 5.25 10.9
  • Example 65 Compound Inv 13 5.34 10.8
  • Example 66 Compound Inv 37 5.42 11.3
  • Example 67 Compound Inv 49 5.38 10.4
  • Example 68 Compound Inv 70 5.30 11.0
  • Example 69 Compound Inv 87 5.64 9.2
  • Example 70 Compound Inv 89 5.32 10.8
  • Example 71 Compound Inv 91 5.48 11.4
  • Example 72 Compound Inv 93 5.36 12.2
  • Example 73 Compound Inv 105 5.43 10.1
  • Example 74 Compound Inv 129 5.38 12.2
  • Example 75 Compound Inv 141 5.52 11.6
  • Example 76 Compound Inv 183 5.29 10.4
  • Example 77 Compound Inv 221 5.30 11.7
  • Example 78 Compound Inv 227 5.13 10.9
  • Example 79 Compound Inv 233 5.37 10.2
  • Example 80 Compound Inv 254 5.34 12.0
  • Example 81 Compound Inv 273 5.
  • the red organic electroluminescent device (the red organic electroluminescent device of Examples 64 to 91) using the compound represented by Formula 1 according to the present invention as a light emitting auxiliary layer material is conventionally used without a light emitting auxiliary layer.
  • the red organic electroluminescent element (the organic electroluminescent element of Comparative Example 3) using only CBP as the material of the light emitting layer, the driving voltage was similar but the light emission efficiency was improved.
  • the compound Inv 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • DS-205 Doosan (80 nm) / NPB (15 nm) / Compound Inv 1 (15nm) / ADN + 5% DS-405 (Doosan) (30nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) in order to prepare a blue organic electroluminescent device.
  • NPB, ADN and BCP used at this time are as follows.
  • a blue organic EL device was manufactured in the same manner as in Example 92, except that each of the compounds shown in Table 4 was used instead of the compound Inv 1 used as the emission auxiliary layer material in the formation of the emission auxiliary layer in Example 92. It was.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 92, except that Compound Inv-1, used in Example 92, was not used.
  • Example 92 Compound Inv 1 5.62 5.9
  • Example 93 Compound Inv 13 5.71 6.2
  • Example 94 Compound Inv 37 5.68 6.5
  • Example 95 Compound Inv 49 5.72 6.3
  • Example 96 Compound Inv 70 5.63 5.4
  • Example 97 Compound Inv 87 5.72 6.1
  • Example 98 Compound Inv 89 5.60 6.4
  • Example 99 Compound Inv 91 5.81 5.3
  • Example 100 Compound Inv 93 5.48 6.8
  • Example 101 Compound Inv 105 5.62 6.3
  • Example 102 Compound Inv 129 5.64 5.9
  • Example 103 Compound Inv 141 5.58 6.5
  • Example 104 Compound Inv 183 5.61 5.8
  • Example 105 Compound Inv 221 5.39 6.3
  • Example 106 Compound Inv 227 5.61 5.4
  • Example 107 Compound Inv 233 5.52 6.5
  • Example 108 Compound Inv 254 5.64 6.6
  • Example 109 Compound Inv 2
  • the blue organic electroluminescent device (the blue organic electroluminescent device of Examples 92 to 119) using the compound represented by Formula 1 according to the present invention as a light emitting auxiliary layer material is conventionally provided without a light emitting auxiliary layer.
  • the blue organic electroluminescent element (the organic electroluminescent element of Comparative Example 4) including only the light emitting layer of ADN, it was found that the driving voltage was similar but the light emission efficiency was improved.

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

Abstract

La présente invention concerne un dispositif électroluminescent organique qui comprend, dans au moins une couche organique, un nouveau composé présentant une excellente résistance à la chaleur, capacité de transport de trous, capacité d'émission de lumière et similaire, et présentant, par conséquent, une efficacité lumineuse, une tension de commande, une durée de vie et des caractéristiques similaires améliorées.
PCT/KR2015/014185 2014-12-24 2015-12-23 Composé organique et dispositif électroluminescent organique comprenant un tel composé WO2016105123A2 (fr)

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WO2019185060A1 (fr) * 2018-03-29 2019-10-03 江苏三月光电科技有限公司 Composé utilisant du bi-diméthylfluorène lié à l'arylamine en tant que noyau, et utilisation associée
CN110317140A (zh) * 2018-03-29 2019-10-11 江苏三月光电科技有限公司 一种以芳胺接双二甲基芴为核心的化合物及其应用
WO2023214815A1 (fr) * 2022-05-06 2023-11-09 (주)피엔에이치테크 Composé organique et dispositif électroluminescent organique le comprenant

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KR101959409B1 (ko) * 2015-09-10 2019-03-18 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
KR102242490B1 (ko) * 2016-01-22 2021-04-21 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이를 사용한 유기 전계 발광 소자
KR20200099249A (ko) 2019-02-13 2020-08-24 삼성디스플레이 주식회사 유기 발광 소자

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JP2001160489A (ja) 1999-12-01 2001-06-12 Toyota Central Res & Dev Lab Inc 有機電界発光素子
KR101233380B1 (ko) * 2009-10-21 2013-02-15 제일모직주식회사 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
JP5652235B2 (ja) * 2011-02-10 2015-01-14 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
KR20140018789A (ko) * 2012-07-31 2014-02-13 에스케이케미칼주식회사 유기전계발광소자용 화합물 및 이를 포함하는 유기전계발광소자
CN104045595A (zh) * 2014-06-25 2014-09-17 北京绿人科技有限责任公司 一种有机化合物及其使用该有机化合物的电致发光器件
KR101512059B1 (ko) 2014-10-06 2015-04-14 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019185060A1 (fr) * 2018-03-29 2019-10-03 江苏三月光电科技有限公司 Composé utilisant du bi-diméthylfluorène lié à l'arylamine en tant que noyau, et utilisation associée
CN110317140A (zh) * 2018-03-29 2019-10-11 江苏三月光电科技有限公司 一种以芳胺接双二甲基芴为核心的化合物及其应用
CN110317140B (zh) * 2018-03-29 2022-05-13 江苏三月科技股份有限公司 一种以芳胺接双二甲基芴为核心的化合物及其应用
WO2023214815A1 (fr) * 2022-05-06 2023-11-09 (주)피엔에이치테크 Composé organique et dispositif électroluminescent organique le comprenant

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