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WO2019143110A1 - Composé organique et élément électroluminescent organique l'utilisant - Google Patents

Composé organique et élément électroluminescent organique l'utilisant Download PDF

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Publication number
WO2019143110A1
WO2019143110A1 PCT/KR2019/000614 KR2019000614W WO2019143110A1 WO 2019143110 A1 WO2019143110 A1 WO 2019143110A1 KR 2019000614 W KR2019000614 W KR 2019000614W WO 2019143110 A1 WO2019143110 A1 WO 2019143110A1
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group
mmol
formula
aryl
bonded
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Korean (ko)
Inventor
이용환
엄민식
홍진석
심재의
박정근
손효석
한송이
박우재
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Doosan Corp
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Doosan Corp
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    • 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
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel compound having excellent thermal stability and light emitting ability, and a novel compound containing the same in one or more organic layers to improve characteristics such as luminous efficiency, And an organic electroluminescent device.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.
  • the light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color.
  • yellow and orange light emitting materials are also used as light emitting materials for realizing better color.
  • a host / dopant system can be used as a light emitting material.
  • the dopant material can 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.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as materials used for the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer, and the anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material .
  • Ir as a phosphorescent material that has a great advantage in improving the efficiency aspects of the light-emitting material (ppy) 3, (acac) Ir (btp) 2
  • Ir metal complex compound is a blue, green and red host material that includes such as . So far, CBP has shown excellent properties as a phosphorescent host material.
  • Patent Document 1 Japanese Laid-Open Patent Publication No. 2001-160489
  • the present invention has been made to solve the above-mentioned problems, and it is an object of the present invention to provide an organic electroluminescent device which can be applied to an organic electroluminescent device and which has excellent thermal stability, hole injection ability, hole transport ability, All aimed at providing excellent novel organic compounds.
  • Another object of the present invention is to provide an organic electroluminescent device including the above-described novel organic compound and exhibiting thermal stability, a low driving voltage and a high luminous efficiency, and having an improved lifetime.
  • the present invention provides a compound represented by the following general formula (1).
  • X 1 and X 2 are the same as or different from each other and each independently O or S,
  • Y 1 to Y 16 are the same as or different from each other, and each independently CR 8 or N, provided that when there are a plurality of CR 8 s , the plurality of R 8 s are the same as or different from each other,
  • Z 1 to Z 3 are the same or different and each independently CR 5 or N, at least one of them is N,
  • Ar 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cycloalkyl, A C 6 to C 60 aryl group,
  • the X 1 containing ring and the X 2 containing ring are asymmetrically bonded to each other based on the Z 1 to Z 3 containing ring,
  • n are each an integer of 0 to 3, m + n? 1,
  • a and B are the same or different from each other, and are each independently any one of substituents represented by the following formula (2) or (3);
  • X 3 is a single bond
  • Ar 2 represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a C 6 to C 60 aryl group, 5 to 60 heteroaryl groups and C 6 to C 60 arylamine groups, or may be bonded to adjacent groups to form a condensed ring,
  • a, c, and f are each an integer of 0 to 3
  • b, d and e are each an integer of 0 to 4, wherein b + m? 4, d + n? 4,
  • R 1 to R 8 are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 An alkynyl group, a C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyl A C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting of an
  • the present invention also provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by the general formula An electroluminescent device is provided.
  • At least one of the organic compound layers including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emission assist layer, a light emitting layer, an electron transport layer, and an electron injection layer, .
  • the compound represented by Formula 1 may be used as a phosphorescent host of the light emitting layer.
  • the compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent properties and can be used as a material of an organic material layer of an organic electroluminescent device.
  • novel compounds according to the invention are prepared by reacting a nitrogen-containing heteroaromatic ring (for example azine) with two dibenzo-based moieties (for example dibenzofuran or dibenzothiophene) non-symmetrically bonded to both sides thereof And a carbazole group, which is a kind of electron donating group (EDG) having an electron donor group, is bonded to at least one phenyl group of the two dibenzo series moieties, Is the basic skeleton.
  • a nitrogen-containing heteroaromatic ring for example azine
  • two dibenzo-based moieties for example dibenzofuran or dibenzothiophene
  • EDG electron donating group
  • the compound of Chemical Formula 1 has dibenzo-type moieties (eg, dibenzofuran (DBF), dibenzothiophene (DBT)) having both physicochemical properties with respect to holes and electrons, (Such as pyridine, pyrazine, and triazine) which is a kind of azine group, which is a large electron withdrawing group (EWG), and at least one carbazole group is connected to the dibenzo series moiety.
  • DPF dibenzofuran
  • DBT dibenzothiophene
  • EWG electron withdrawing group
  • the compound of Formula 1 is a bipolar compound, the recombination of holes and electrons is high, so that the hole injecting / transporting ability, luminous efficiency, driving voltage, lifetime characteristics, durability and the like can be improved.
  • the compound of formula (1) when used as a green phosphorescent material, not only excellent luminous efficiency characteristics but also low voltage driving ability can be obtained and lifetime can be increased, and thermal stability, high glass transition temperature characteristics and uniform morphology morphology). Since the organic EL device is also effective in inhibiting crystallization of the organic material layer, the performance and lifetime characteristics of the organic EL device including the compound can be greatly improved.
  • the planarity and stereoscopic property of the compound can be realized according to the bonding positions of two dibenzofurans or dibenzothiophene moieties bonded to azine groups.
  • the electron transporting ability is improved, and the driving and efficiency of the device to which these compounds are applied can be expected to be increased.
  • the dibenzofuran moiety or the dibenzothiophene moiety is more excellent in electron and hole stability than an aryl group, lifetime characteristics of a device to which such a compound is applied can be further improved.
  • two dibenzo-based moieties bonded to an azine group exhibit an asymmetric structure.
  • This asymmetric structure compound is easier to control the HOMO-LUMO value than a symmetric structure compound.
  • an asymmetric structural compound having a dibenzo-based moiety it is relatively easy to control the intermolecular distance as compared with a compound having a symmetric structure. That is, due to the nature of the dibenzo-based moiety capable of bonding at the 1,2,3,4-position, a structural disorder between the hydrogen of triazine and the dibenzo-based moiety occurs at the 1,4-bond, The distance will be farther away, which will also increase the T1 value.
  • At least one carbazole group in the form of a non-fused ring is introduced as an electron donor (EDG).
  • EDG electron donor
  • This carbazole group is electrochemically stable and has a deep HOMO level by conjugation with other amines EDG.
  • the carbazole group is also excellent in thermal stability and electrochemical stability, and has a high glass transition temperature (Tg) and excellent carrier transporting ability. Particularly, the electron and hole transport mobility is very excellent, and the balance of the carriers in the light emitting layer is very excellent.
  • the host material should have a triplet energy gap higher than the dopant of the host. That is, in order to effectively provide phosphorescent emission from the dopant, the lowest excitation state of the host must be higher energy than the lowest emission state of the dopant.
  • the compound represented by Formula 1 has a high triplet energy and can be used as a host material because the energy level can be controlled higher than that of the dopant.
  • the compound represented by the formula (1) can prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Accordingly, the luminous efficiency of the device can be improved by increasing the number of the excitons contributing to the light emission in the light emitting layer, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased.
  • the compound represented by the above formula (1) can improve the phosphorescence characteristics of the organic electroluminescent device and improve the electron injection / transport ability, luminous efficiency, driving voltage and lifetime characteristics. Therefore, the compound of Chemical Formula (1) according to the present invention can be used as a material of any one of a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer which is an organic material layer of an organic electroluminescent device, , Green and / or red phosphorescent host material).
  • the compound represented by formula (1) of the present invention when used as a blue, green and / or red phosphorescent host material, preferably phosphorescent green n-type host and / or phosphor red host, for example, a full color display panel having a low driving voltage, a high efficiency and a long lifetime compared with the organic electroluminescent device can be manufactured, and a high efficiency and a long life can be improved.
  • the compound represented by the general formula (1) according to the present invention is a compound represented by the general formula (1), which comprises an azine group and two dibenzo-based moieties (dibenzofuran or dibenzothiophene moiety) At least one carbazole group, which is a kind of electron donor (EDG), is bonded to any one of six-membered rings (e.g., phenyl group) in the core.
  • EDG electron donor
  • X 1 and X 2 are the same as or different from each other and each independently O or S. At this time, when d is 0, dibenzofuran moiety is formed, and in case of S, dibenzothiophene moiety can be formed.
  • Y 1 to Y 16 are the same as or different from each other, and each independently CR 8 or N; In this case, when there are a plurality of CR 8 s , the plurality of R 8 s may be the same or different.
  • the remaining is CR 8 ;
  • At least one of Y 13 to Y 16 is N, the remaining is CR 8 ;
  • At least one of Y 1 to Y 4 is N, and at least one of Y 9 to Y 12 is N, the remainder is CR 8 ;
  • At least one of Y 5 to Y 8 is N, and at least one of Y 13 to Y 16 is N, the remainder is CR 8 ;
  • At least one of Y 1 to Y 4 is N, and when one of Y 13 to Y 16 is N, the remaining is CR 8 ;
  • Y 1 to Y 16 may all be CR 8 (see the following formulas 9 to 13).
  • R 8 is hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, an alkynyl group of C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ C 60 aryloxy group, C group 1 ⁇ C 40 alkyl silyl, C 6 ⁇ C 60 aryl silyl group, a alkyl boronic of C 1 ⁇ C 40, an aryl boronic a C 6 ⁇ C 60, C 1 ⁇ C 40 phosphine groups, C 1 to C 40 phosphine oxide groups, and C 6 to C 60
  • R 8 is a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 of the A cycloalkyl group, and a C 6 to C 60 aryl group.
  • Z 1 to Z 3 are the same or different and are each independently CR 5 or N, and at least one of them is N. In one preferred embodiment, from 1 to 3 of Z 1 to Z 3 may be N, for example, pyridine, pyrimidine, triazine. More preferably, all of Z 1 to Z 3 are N and triazine is electron-withdrawing.
  • Ar 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cycloalkyl, A C 6 to C 60 aryl group, and the like.
  • Ar 1 is preferably an aryl group of C 6 to C 60 , and may be, for example, a phenyl group, a biphenyl group, a naphthyl group, a triphenyl group, an anthryl group, a phenanthryl group and the like.
  • Ar 1 can be selected from the group of substituents represented by the following structural formulas.
  • Ar 1 may be substituted with at least one substituent group known in the art (for example, the same definition as R 6 ).
  • a and c are each an integer of 0 to 3
  • b and d are an integer of 0 to 4, respectively.
  • hydrogen means not substituted with R 1 to R 4
  • a to d are each an integer of 1 or more, one or more hydrogen atoms are substituted with R 1 to R 4 . it means.
  • R 1 to R 5 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the An alkynyl group, a C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyl A C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6
  • R 1 to R 5 each are plural, they are the same as or different from each other. Specifically, R 1 to R 5 are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 An alkynyl group of C 40 to C 40 , a cycloalkyl group of C 3 to C 40 , and an aryl group of C 6 to C 60 .
  • m and n are each an integer of 0 to 3, and m + n? 1.
  • m or n 0, it means that hydrogen is not substituted with A or B.
  • m and n are each an integer of 1 or more, it means that at least one hydrogen is substituted with A and B, respectively.
  • m and n may each be an integer of 0 to 2.
  • b + m and d + n may be an integer of 0 to 4, respectively.
  • a and B are electron donating substituents each of which serves to provide electrons.
  • EDG electron donating group
  • a and B are the same as or different from each other, and each independently may be any of the substituents represented by the above-described formulas (2) and (3).
  • e is an integer of 0 to 4
  • f is an integer of 0 to 3.
  • hydrogen means not substituted by R 6 and R 7
  • e and f are each an integer of 1 or more, at least one hydrogen is substituted with R 6 and R 7 respectively .
  • R 6 and R 7 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C A C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkenyl group, C 6 -C 60 aryloxy groups, C 1 -C 40 alkylsilyl groups, C 6 -C 60 arylsilyl groups, C 1 -C 40 alkylboron groups, C 6 -C 60 a group of the arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the
  • R 6 and R 7 are plural, they may be the same as or different from each other.
  • R 6 and R 7 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 A C 3 to C 40 cycloalkyl group, and a C 6 to C 60 aryl group, or may be bonded to adjacent groups to form a condensed ring.
  • adjacent groups may be one R 6 and one R 6 , one R 6 and one Ar 2 , one R 7 and another R 7 , one R 7, and one Ar 2 .
  • Ar 2 represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ , or selected from the group consisting of an aryl amine of the C 60, or adjacent groups condensed in combination with (for example, R 6, R 7) A ring can be formed.
  • the Ar 2 may be selected from the group consisting of an aryl amine of the C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ C 60.
  • a and B are the same as or different from each other, and each independently can be any one selected from the group of substituents represented by the following structural formulas.
  • Ar 2 is the same as defined in formula (1). Although not specifically shown, the above-mentioned structural formula may be substituted with at least one substituent group known in the art (for example, the same definition as R 6 ).
  • Ar 1 to Ar 2 , and R 1 to R 8 are independently selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, A halogen atom, a cyano group, a nitro group, a C 2 to C 40 alkenyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, alkynyl of C 2 ⁇ C 40, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ aryl group of C 60, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryloxy group,
  • the nitrogen-containing heterocycle having an EWG properties (such as, Z 1 ⁇ Z 3 containing ring) 2 dibenzo-based moiety that is bonded to (for example, X 1 hamyuhwan and X 2- containing rings) according to the positions of the carbon bonds of the asymmetric structure.
  • the bonding position of one of Y 1 to Y 4 of the X 1 containing ring connected to the Z 1 to Z 3 containing ring and the bonding position of one of Y 9 to Y 12 of the X 2 containing ring are asymmetric with each other .
  • the O rare cases (for example, Z 1 ⁇ Z 3-containing ring) is X 1 containing ring carbon position coupled to Y 1 il, X 2 containing ring carbon position which is bonded to the azine is Y 10 to the exception of Y 9 Y 12 (see Chemical Formula 4 below).
  • the carbon bond positions of two dibenzo-based moieties respectively linked to the nitrogen-containing heterocycle may be represented by any one of the following formulas (4) to (7).
  • the ring containing Z 1 to Z 3 in Formula 4 is bonded to any one of Y 10 to Y 12 (provided that the ring containing Z 1 to Z 3 is not bonded to Y 9 )
  • the ring containing Z 1 to Z 3 in Formula 5 is bonded to any one of Y 9 and Y 11 to Y 12 (provided that the ring containing Z 1 to Z 3 is not bonded to Y 10 )
  • the ring containing Z 1 to Z 3 in Formula 6 is bonded to any one of Y 9 , Y 10 and Y 12 (provided that the Z 1 to Z 3 containing ring is not bonded to Y 11 )
  • the ring containing Z 1 to Z 3 in the above formula (7) is bonded to any one of Y 9 to Y 11 (provided that the Z 1 to Z 3 containing ring is not bonded to Y 12 )
  • X 1 , X 2 , Y 1 to Y 16 , Z 1 to Z 3 , Ar 1 , m, n, A, B, a to d and R 1 to R 4 are as defined in Formula 1, respectively.
  • the compound represented by Formula 4 may be further represented by any one of Formulas 4a to 4c.
  • the compound represented by Formula 5 may be further represented by any one of Formulas 5a to 5c.
  • the compound represented by Formula 6 may be further represented by any one of Formulas 6a to 6c.
  • the compound represented by the above formula (7) may be further represented by any one of formulas (7a) to (7c).
  • dibenzo-based moieties such as dibenzofurane or dibenzothiophene moiety may be further represented by any one of the following formulas (8) to (12).
  • X 1 , X 2 , Z 1 to Z 3 , Ar 1 , n, A and B are as defined in the above formula (1).
  • each of X 1 and X 2 is independently O or S, and Z 1 to Z 3 are each independently CR 5 or N, a is N, Ar 1 is an aryl group of C 6 ⁇ C 60.
  • the carbon position of the X 1 -containing ring and the carbon position of the X 2 -containing ring bonded to the azine group (for example, the Z 1 to Z 3 -containing ring) have an asymmetric structure, and at least one of A and B is a carbazole group Lt; / RTI >
  • the compound represented by formula (1) according to the present invention may be further represented by any one of compounds 1 to 500 shown below.
  • the compounds represented by formula (1) of the present invention are not limited by the following examples.
  • alkyl means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms.
  • alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.
  • alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond.
  • alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond.
  • alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Aryl in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included.
  • heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • alkyloxy means a monovalent substituent group represented by R'O-, and R 'means alkyl having 1 to 40 carbon atoms.
  • alkyloxy may include linear, branched or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.
  • aryloxy means a monovalent substituent represented by RO-, and R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • Alkylsilyl in the present invention refers to silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • alkyl boron is boron substituted with alkyl having 1 to 40 carbon atoms
  • aryl boron means boron substituted with aryl having 6 to 60 carbon atoms.
  • arylphosphine means a phosphine substituted with aryl having 6 to 60 carbon atoms
  • arylphosphine oxide group means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O do.
  • condensed rings means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • the compounds represented by formula (1) of the present invention can be prepared without limitation by methods known in the art. For example, various syntheses can be carried out by referring to the synthesis process of the following examples.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).
  • the organic electroluminescent device includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1).
  • the compounds may be used alone or in combination of two or more.
  • the at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer.
  • the organic compound layer containing the compound of Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescence device of the present invention may include a host material (preferably, a phosphorescent host material).
  • the light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode sequentially stacked Structure. At least one of the hole injecting layer, the hole transporting layer, the light-emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, ≪ / RTI > compounds. Further, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.
  • the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.
  • 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.
  • the substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.
  • the positive electrode material examples 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); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • 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; And multi-layer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.
  • the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and ordinary materials known in the art can be used.
  • NBS (11.1 g, 62.1 mmol) was added to 150 mL of a methylene chloride mixture with 2 ', 4'-dichloro- [1,1'-biphenyl] -2-ol (13.5 g, 56.5 mmol) and Diisopropylamine ) was slowly added thereto and stirred at 40 ° C for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and sodium thiosulfate aqueous solution, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, 3-bromo-2 ', 4'-dichloro- [1,1'-biphenyl] -2-ol (13.5 g, yield 75%) .
  • the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the desired compound C2 (8.5 g, yield 85%) was obtained by column chromatography.
  • NBS (13.6 g, 76.4 mmol) was added to 200 mL of a methylene chloride mixture of 2 ', 6'-dichloro- [1,1'-biphenyl] -2-ol (16.6 g, 69.4 mmol) and Diisopropylamine ) was slowly added thereto and stirred at 40 ° C for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and sodium thiosulfate aqueous solution, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, 3-bromo-2 ', 6'-dichloro- [1,1'-biphenyl] -2-ol (17.0 g, yield 77%) .
  • Tri-tert-butylphosphine (0.9 mL, 3.7 mmol) was added and the mixture was stirred at 110 ° C for 8 hours. After completion of the reaction, the product was extracted, and the solvent was removed. The solid was dissolved in toluene to remove silica, and then the desired product, 9- (8-chlorodibenzo [b, d] furan- carbazole (11.51 g, yield 51%).
  • 2,3,4-trichloropyridine (100.0 g, 548.1 mmol) and 2-methoxyphenyl boronic acid (87.5 g, 141.7 mmol) are placed in a 2-neck flask at room temperature.
  • Pd (PPh 3) 4 (19.0 g, 16.4mmol) and KF (47.8 g, 822.2 mmol) is added.
  • the mixture is stirred at 100 ° C for 5 hours. After completion of the reaction, the solution is subjected to silica filtration.
  • 3,4-dichloro-2- (2-methoxyphenyl) pyridine (40.0 g, 157.4 mmol) is dissolved in 400 ml of methylene chloride and placed in a 2-neck flask. Keep the condition at 0 °C in an ice bath. Of BBr 3 (22.7 ml, 236.1 mmol ) was slowly added. After completion of the reaction, 400 ml of distilled water at 0 ° C is slowly added. The reaction is extracted with methylene chloride and silica filtered. After removal of the solvent, a white solid compound, 2- (3,4-dichloropyridin-2-yl) phenol (31.4 g, yield 83%) was obtained.
  • a glass substrate coated with ITO Indium Tin Oxide
  • ITO Indium Tin Oxide
  • the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
  • a solvent such as isopropyl alcohol, acetone, or methanol
  • a green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound 119 as a luminescent host material in forming the light emitting layer.
  • a green organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound I was used instead of Compound 119 as a luminescent host material in forming the light emitting layer.
  • a green organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound II was used instead of Compound 119 as a luminescent host material in forming the light emitting layer.
  • the driving voltage, current efficiency and emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices manufactured in Examples 1 to 21 and Comparative Examples 1 to 3, Respectively.
  • Example 1 119 4.62 516 55.5 Example 2 239 4.55 516 62.1 Example 3 219 5.46 516 42.1 Example 4 59 5.33 516 43.0 Example 5 99 4.95 516 51.2 Example 6 240 5.01 516 53.1 Example 7 118 4.88 516 48.2 Example 8 117 4.58 516 40.2 Example 9 254 5.11 516 55.5 Example 10 284 4.76 516 42.1 Example 11 304 4.54 516 58.0 Example 12 360 4.99 516 52.7 Example 13 386 5.01 516 55.5 Example 14 259 4.21 516 56.3 Example 15 266 5.46 516 49.6 Example 16 290 4.87 516 47.2 Example 17 289 5.21 516 53.1 Example 18 409 4.77 516 52.1 Example 19 407 4.56 516 53.3 Example 20 415 4.99 516 47.7 Example 21 481 4.89 516 56.6 Comparative Example 1 CBP 6.93 516 38.2 Comparative Example 2
  • the green organic electroluminescent devices of Examples 1 to 21, in which the compound according to the present invention was applied to the light emitting layer were compared with the green organic electroluminescent devices of Comparative Examples 1 to 3 in which CBP, It was found that the current efficiency and the driving voltage were superior to those of the electroluminescent device.

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Abstract

La présente invention concerne un nouveau composé organique et un élément électroluminescent organique l'utilisant, et plus particulièrement, l'invention concerne un nouveau composé ayant d'excellente capacité d'émission de lumière et un élément électroluminescent organique présentant des caractéristiques améliorées, telles qu'une efficacité d'émission de lumière élevée, une faible tension de commande et une longue durée de vie, en contenant le nouveau composé dans au moins une couche de matériau organique.
PCT/KR2019/000614 2018-01-16 2019-01-15 Composé organique et élément électroluminescent organique l'utilisant Ceased WO2019143110A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008072596A1 (fr) * 2006-12-13 2008-06-19 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, dispositif d'affichage et d'éclairage
WO2013069242A1 (fr) * 2011-11-07 2013-05-16 出光興産株式会社 Matière pour éléments électroluminescents organiques et élément électroluminescent organique l'utilisant
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
KR20170053590A (ko) * 2015-11-06 2017-05-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170067671A (ko) * 2015-12-08 2017-06-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170113321A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008072596A1 (fr) * 2006-12-13 2008-06-19 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, dispositif d'affichage et d'éclairage
WO2013069242A1 (fr) * 2011-11-07 2013-05-16 出光興産株式会社 Matière pour éléments électroluminescents organiques et élément électroluminescent organique l'utilisant
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
KR20170053590A (ko) * 2015-11-06 2017-05-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170067671A (ko) * 2015-12-08 2017-06-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170113321A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자

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