WO2023182775A1 - Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant - Google Patents

Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant Download PDF

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WO2023182775A1
WO2023182775A1 PCT/KR2023/003724 KR2023003724W WO2023182775A1 WO 2023182775 A1 WO2023182775 A1 WO 2023182775A1 KR 2023003724 W KR2023003724 W KR 2023003724W WO 2023182775 A1 WO2023182775 A1 WO 2023182775A1
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정재경
최호정
신봉기
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에스에프씨 주식회사
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Definitions

  • the present invention relates to a novel compound that can be used in organic light-emitting devices, and more specifically, to a novel compound that can be used as a host material for the light-emitting layer in an organic light-emitting device, through which device characteristics of low voltage, high efficiency, and long lifespan can be realized. It relates to a heterocyclic compound and an organic light-emitting device containing the same.
  • OLED Organic light emitting diode
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • this organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.
  • Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function.
  • the light-emitting materials can be classified into high-molecular-type and low-molecular-type types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. .
  • a host-dopant system can be used as a light-emitting material to increase light-emitting efficiency through transition.
  • the principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
  • heterocyclic compounds containing heteroatoms such as nitrogen and oxygen have recently been studied as host compounds for organic light-emitting devices using phosphorescence, and related prior art is published in Patent Publication No. 10-2023-0028739 ( 2023.03.02) presents an organic light-emitting device using carbazole-structured aromatic heterocyclic compounds as first and second host materials, respectively, and in Patent Publication No. 10-2020-0139834 (2020.12.14), polycyclic An organic light-emitting device containing a ring-structured aromatic heterocyclic compound as a phosphorescent host It is listed.
  • the first technical task to be achieved by the present invention is to provide a novel organic compound that can be used as a phosphorescent host material for the light-emitting layer in an organic light-emitting device.
  • the second technical problem to be achieved by the present invention is to provide a low-voltage, high-efficiency, and long-life organic light emitting diode (OLED) containing the organic compound as a host material in the organic light emitting device.
  • OLED organic light emitting diode
  • the present invention provides an aromatic heterocyclic compound represented by [Formula A] or [Formula B] below.
  • the X 1 is any one selected from NR 4 , O and S,
  • Z 1 to Z 8 are the same or different from each other, and are each independently selected from CR or N,
  • each R is the same as or different from each other
  • One of Z 3 to Z 6 is a carbon atom containing a single bond bonded to the linking group L,
  • R, R 1 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted.
  • a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted Alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms Any one selected from a thio group, a substituted or unsubstituted amine group with 0 to 30 carbon atoms, a substituted or unsubstituted silyl group with 0 to 30 carbon atoms, a germanium group with 0 to 30 carbon atoms, a
  • each R adjacent to each other may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic ring may be
  • the carbon atom of the monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
  • R 2 and R 3 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
  • L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
  • alkyl group cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 7 to 24 carbon atoms, and an aromatic group having 5 to 24 carbon atoms.
  • Cycloalkyl group with a condensed hetero ring a heterocycloalkyl group with a condensed aromatic hydrocarbon ring having 6 to 24 carbon atoms, an aryl group with a condensed aliphatic hydrocarbon ring with 8 to 24 carbon atoms, and a condensed aliphatic hydrocarbon ring with 5 to 24 carbon atoms.
  • heteroaryl group alkoxy group of 1 to 24 carbon atoms, amine group of 1 to 24 carbon atoms, silyl group of 1 to 24 carbon atoms, germanium group of 1 to 24 carbon atoms, aryloxy group of 6 to 24 carbon atoms, 6 to 24 carbon atoms means being substituted with one or more substituents selected from the group consisting of arylthionyl groups, and one or more hydrogens in each substituent can be replaced with deuterium.
  • aromatic heterocyclic compound represented by Formula A or Formula B according to the present invention When used as a phosphorescent host material for the light-emitting layer in an organic light-emitting device, it has lower voltage, higher efficiency, and longer lifespan compared to the organic light-emitting device according to the prior art.
  • An organic light emitting device that can be implemented can be provided.
  • FIG. 1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention.
  • the present invention provides an aromatic heterocyclic compound represented by the following [Formula A] or [Formula B].
  • the X 1 is any one selected from NR 4 , O and S,
  • Z 1 to Z 8 are the same or different from each other, and are each independently selected from CR or N,
  • each R is the same as or different from each other
  • One of Z 3 to Z 6 is a carbon atom containing a single bond bonded to the linking group L,
  • R, R 1 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted.
  • a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted Alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms Any one selected from a thio group, a substituted or unsubstituted amine group with 0 to 30 carbon atoms, a substituted or unsubstituted silyl group with 0 to 30 carbon atoms, a germanium group with 0 to 30 carbon atoms, a
  • each R adjacent to each other may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring, and the formed alicyclic or aromatic ring may be
  • the carbon atom of the monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S and O,
  • R 2 and R 3 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring,
  • L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
  • alkyl group cycloalkyl group with 3 to 30 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, arylalkyl group with 7 to 24 carbon atoms , an alkylaryl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, a cycloalkyl group in which an aromatic hydrocarbon ring is condensed, having 7 to 24 carbon atoms, and an aromatic group having 5 to 24 carbon atoms.
  • Cycloalkyl group with a condensed hetero ring a heterocycloalkyl group with a condensed aromatic hydrocarbon ring having 6 to 24 carbon atoms, an aryl group with a condensed aliphatic hydrocarbon ring with 8 to 24 carbon atoms, and a condensed aliphatic hydrocarbon ring with 5 to 24 carbon atoms.
  • heteroaryl group alkoxy group of 1 to 24 carbon atoms, amine group of 1 to 24 carbon atoms, silyl group of 1 to 24 carbon atoms, germanium group of 1 to 24 carbon atoms, aryloxy group of 6 to 24 carbon atoms, 6 to 24 carbon atoms means being substituted with one or more substituents selected from the group consisting of arylthionyl groups, and one or more hydrogens in each substituent can be replaced with deuterium.
  • the range of the carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl portion or aryl portion when the substituent is regarded as unsubstituted without considering the substituted portion, respectively.
  • a phenyl group substituted with a butyl group at the para position should be viewed as corresponding to an aryl group with 6 carbon atoms substituted with a butyl group with 4 carbon atoms.
  • the aryl group which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen. When the aryl group has a substituent, it can be fused with neighboring substituents to further form a ring. Additionally, the aryl group may include an organic radical obtained by removing one hydrogen from an arene ring formed by condensing two arene rings.
  • aryl group examples include phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic radical groups such as pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl group, fluoranthenyl group, etc. can be mentioned, and the fluorene ring and the phenylene ring are condensed.
  • It may also include an organic radical resulting from the removal of one hydrogen in an arene ring formed by condensing two arene rings, such as an arene ring or an arene ring in which a fluorene ring and a phenanthrene ring are condensed.
  • one or more hydrogen atoms of the aryl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH 2 , -NH(R), -N(R')(R'' ), R' and R" are independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group”), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, carbon number 1 to 24 alkyl group, halogenated alkyl group with 1 to 24 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, aryl with 7 to 24 carbon carbon atom
  • the aromatic hydrocarbon ring refers to an aromatic ring made up of carbon and hydrogen
  • the aliphatic hydrocarbon ring refers to a hydrocarbon ring made up of carbon and hydrogen but does not belong to the aromatic hydrocarbon ring.
  • the aliphatic ring refers to a hydrocarbon ring made up of carbon and hydrogen.
  • the hydrocarbon ring is preferably a hydrocarbon ring in which at least 30% or more of the carbon atoms forming the ring are bonded through an sp 3 orbital structure and contain 0 to 3 double bonds and/or triple bonds in the ring. , more preferably, at least 50% or more of the carbon atoms forming the ring are bonded by sp 3 orbitals, and may be a hydrocarbon ring containing 0 to 2 double bonds and/or triple bonds in the ring.
  • the aryl group in which the aliphatic hydrocarbon ring is condensed consists of two carbon atoms adjacent to each other in the aliphatic hydrocarbon ring and two carbon atoms excluding the carbon atom that becomes an organic radical by removing the hydrogen of one of the carbon atoms forming the ring in the aryl group. It refers to a cyclic substituent in which two adjacent carbon atoms are condensed together to share one double bond and has overall non-aromaticity. Specific examples include tetrahydronaphthyl group, tetrahydrobenzocycloheptene, and tetrahydrophene. Nantrene group, tetrahydroanthracenyl group, octahydrotriphenylene group, etc. are mentioned.
  • the heteroaryl group which is a substituent used in the compound of the present invention, contains 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in the aromatic ring, and the remaining ring atom is carbon. It refers to an aryl group of an aromatic system with 2 to 24 rings, and the rings can be fused to form a ring. And one or more hydrogen atoms of the heteroaryl group may be replaced with the same substituent as that of the aryl group.
  • the aromatic heterocycle means that one or more aromatic carbons in the aromatic hydrocarbon ring are substituted with a hetero atom
  • the aromatic hetero ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring consisting of N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.
  • heteroaryl groups in which aliphatic hydrocarbon rings are condensed A substituent having a structure in which a heteroaryl group is substituted for an aryl group in the aryl group in which the aliphatic hydrocarbon ring is condensed, specific examples include tetrahydroindole group, tetrahydrobenzofuranyl group, tetrahydrobenzothiophene group, tetrahydrocarbazole group, Tetrahydrodibenzofuranyl group, tetrahydrobenzothiophene group, tetrahydroquinoline group, tetrahydroquinoxaline group, etc. are mentioned.
  • the aromatic heterocycle means that one or more aromatic carbons in the aromatic hydrocarbon ring are substituted with a hetero atom
  • the aromatic hetero ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring consisting of N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.
  • the 'condensed ring in which an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring are condensed means a condensed ring in which two adjacent carbon atoms of an aromatic hydrocarbon ring and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared.
  • Examples include a tetrahydronaphthalene ring in which two carbon atoms adjacent to each other in a benzene ring and a cyclohexane ring are shared and condensed.
  • the 'condensed ring in which an aromatic heterocycle and an aliphatic hydrocarbon ring are condensed' is a condensed ring in which two adjacent carbon atoms of an aromatic heterocycle and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared. It means, and an example is a hexahydrodibenzofuran ring in which two adjacent carbon atoms in each ring of a benzofuran ring and a cyclohexane ring are shared and condensed.
  • the alkyl group which is a substituent used in the present invention, is a substituent in which one hydrogen is removed from an alkane, and has a straight-chain and branched structure, and specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, and sec. -butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one or more hydrogen atoms of the alkyl group may be replaced with the same substituent as that of the aryl group.
  • 'Cyclo' in the cycloalkyl group, cycloalkoxy group, etc. which are substituents used in the compound of the present invention, refers to a substituent with a structure capable of forming a single ring or multiple rings of a saturated hydrocarbon in an alkyl or alkoxy group, for example, the specific substituent of the cycloalkyl group.
  • Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, Isobornyl, etc. may be mentioned, and one or more hydrogen atoms of the cycloalkyl group may be replaced by the same substituent as that of the aryl group, and this may also be applied to cycloalkoxy.
  • the heterocycloalkyl group means that at least one carbon in the ring of the substituent forming the cycloalkyl structure is substituted with a hetero atom, preferably, 1 to 3 carbons are N, O, P, S, It may be substituted with one or more heteroatoms selected from Si, Ge, Se, and Te.
  • the cycloalkyl group in which the aromatic hydrocarbon ring or aromatic hetero ring is condensed contains two carbon atoms adjacent to each other in the aromatic hydrocarbon ring or aromatic hetero ring; and an organic radical by removal of hydrogen from one of the carbon atoms forming the ring in the cycloalkyl group.
  • the heterocycloalkyl group in which the aromatic hydrocarbon ring is condensed means that one or more carbon atoms in the cycloalkyl ring in the cycloalkyl group in which the aromatic hydrocarbon ring is condensed are substituted with a hetero atom, and preferably 1 to 1 in the cycloalkyl ring. It is a substituent in which three carbons are substituted with one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te. Specific examples include hexahydrodibenzofuranyl group, hexahydrocarbazole group, and hexahydrodi. Benzothiophene group, dihydrobenzodioxine group, etc. are included, and overall, it shows non-aromaticity.
  • an aryl group or heteroaryl group in which an aliphatic heterocycle is condensed A substituent having a structure in which an aliphatic heterocycle is condensed instead of an aliphatic hydrocarbon ring in the aryl group or heteroaryl group in which the aliphatic hydrocarbon ring is condensed.
  • Specific examples include chroman group, dihydropyranopyridine group, thiochroman group, and dihydrobenzodioxin. group, dihydrothiopyranopyridine group, dihydropyranopyrimidine group, etc., and shows non-aromaticity overall.
  • the aliphatic heterocycle means that at least one carbon in the aliphatic hydrocarbon ring is substituted with a hetero atom, and the aliphatic heterocycle preferably has 1 to 3 carbon atoms in the aliphatic hydrocarbon ring at least one hetero atom selected from N, O, or S. It can be replaced with an atom.
  • the alkoxy group which is a substituent used in the compound of the present invention, is a substituent in which an oxygen atom is bonded to the end of an alkyl group or cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, and iso.
  • at least one hydrogen atom of the alkoxy group is the aryl group. It can be substituted with the same substituent as in the case of.
  • One or more hydrogen atoms in the aryl group may be replaced with the same substituent as in the case of the aryl group.
  • silyl group as a substituent used in the compound of the present invention examples include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, and methylcyclobutylsilyl. , dimethylfurylsilyl, etc., and one or more hydrogen atoms of the silyl group may be replaced with the same substituent as that of the aryl group.
  • an alkenyl group refers to an alkyl substituent containing one carbon-carbon double bond made up of two carbon atoms
  • an alkynyl group means one made up of two carbon atoms. It refers to an alkyl substituent containing a carbon-carbon triple bond.
  • the alkylene group used in the present invention is an organic radical derived by removing two hydrogens in an alkane molecule, which is a straight-chain or branched saturated hydrocarbon.
  • the alkylene group include methylene group. , ethylene group, propylene group, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group, pentylene group, iso-amylene group, hexylene group, etc., and hydrogen at least one of the alkylene groups Atoms can be substituted with the same substituents as in the case of the aryl group above.
  • diarylamino group refers to an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom
  • diheteroarylamino group in the present invention refers to an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom
  • the aryl (heteroaryl) amino group refers to an amine group in which the aryl group and the heteroaryl group are each bonded to a nitrogen atom.
  • this is deuterium, cyano group, halogen group, hydroxy group, nitro group, carbon number 1 to 12 alkyl group, halogenated alkyl group with 1 to 12 carbon atoms, alkenyl group with 2 to 12 carbon atoms, alkynyl group with 2 to 12 carbon atoms, cycloalkyl group with 3 to 12 carbon atoms, heteroalkyl group with 1 to 12 carbon atoms, aryl with 6 to 18 carbon atoms group, arylalkyl group with 7 to 20 carbon atoms, alkylaryl group with 7 to 20 carbon atoms, heteroaryl group with 2 to 18 carbon atoms, heteroarylalkyl group with 3 to 18 carbon atoms, alkylheteroaryl group with 3 to 18 carbon atoms, 9 to 9 carbon atoms
  • Aryl group in which a hydrocarbon ring is condensed a heteroaryl group in which an aliphatic hydrocarbon ring having 7 to 20 carbon atoms is condensed,
  • An alkoxy group with 1 to 12 carbon atoms an amine group with 1 to 18 carbon atoms, a silyl group with 1 to 18 carbon atoms, a germanium group with 1 to 18 carbon atoms, an aryloxy group with 6 to 18 carbon atoms, and an arylthionyl group with 6 to 18 carbon atoms. It may be substituted with one or more substituents selected from the group consisting of, and one or more hydrogens in each substituent may be replaced with deuterium.
  • the cycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring having 7 to 30 carbon atoms is condensed it is a cycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring having 9 to 20 carbon atoms is condensed. It may be a cycloalkyl group.
  • the cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed it is a cycloalkyl group in which a substituted or unsubstituted aromatic heteroring having 7 to 20 carbon atoms is condensed. It may be a cycloalkyl group.
  • the substituted or unsubstituted carbon number is 6
  • a heterocycloalkyl group in which a 30 to 30 aromatic hydrocarbon ring is condensed it may be a substituted or unsubstituted heterocycloalkyl group in which a 9 to 20 carbon atom aromatic hydrocarbon ring is condensed.
  • the aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is condensed it is an aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 9 to 20 carbon atoms is condensed. It may be an aryl group.
  • the heteroaryl group in which the substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed it is a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms in which the aliphatic hydrocarbon ring is condensed. It may be a heteroaryl group.
  • an aryl group in which a substituted or unsubstituted aliphatic heterocycle having 6 to 30 carbon atoms is condensed it is an aryl group in which a substituted or unsubstituted aliphatic heteroring having 7 to 20 carbon atoms is condensed. It may be an aryl group.
  • heteroaryl group in which a substituted or unsubstituted aliphatic heterocycle having 5 to 30 carbon atoms is condensed it is a group in which a substituted or unsubstituted aliphatic heteroring having 6 to 20 carbon atoms is condensed. It may be a heteroaryl group.
  • 'R 2 and R 3 may be connected to each other to additionally form an alicyclic or aromatic single or polycyclic ring', this means that one hydrogen radical from each of R 2 and R 3 This means that an additional ring can be formed by removing and connecting them.
  • the aromatic heterocyclic compound represented by [Formula A] or [Formula B] is an aromatic heterocyclic compound containing X 1 and a nitrogen atom (N) in a phenanthrene-like ring containing Z 1 to Z 8 It has a parent core structure in which a pentagonal ring is condensed, and a substituent R 1 is bonded to the aromatic carbon atom bonded to One of Z 3 to Z 6 is an amine substituent ( ) has a technical characteristic of being a carbon atom containing a single bond bonded to the linking group L.
  • X 1 in Formula A and Formula B may be O or S.
  • R 1 to R 4 in Formula A and Formula B are preferably the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. , a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.
  • At least one of R 1 to R 3 in Formula A and Formula B may be an aryl group having 6 to 24 carbon atoms, and more preferably, at least one of R 1 to R 3 is It may be any one selected from Structural Formulas 1 to 6 below.
  • Z is any one selected from NR 5 , CR 6 R 7 , O and S,
  • R 5 to R 7 are the same as R 1 to R 4 ,
  • the carbon site of the aromatic ring may be bonded to one or more selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 18 carbon atoms.
  • At least one of R 1 to R 3 in the aromatic heterocyclic compound may be a substituent represented by [Structural Formula A] below.
  • Q is any one ring selected from the structural formulas Q-1 to Q-3 below,
  • a pair of substituents among the neighboring carbon atoms R 17 and R 18 , R 18 and R 19 , and R 19 and R 20 in structural formula Q-1 are aromatic carbon atoms in structural formula A. It is a single bond that is condensed with f and the aromatic carbon atom g to form a 6-membered ring,
  • substituents R 11 to R 16 and R 17 to R 44 are the same or different from each other, and each independently represents hydrogen, deuterium, deuterium, substituted or unsubstituted carbon atoms of 1 to 24.
  • Alkyl group deuterated or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, deuterated or unsubstituted alkenyl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted Alkynyl group having 2 to 24 carbon atoms, deuterated or unsubstituted heteroalkyl group having 1 to 24 carbon atoms, deuterated or unsubstituted aryl group having 6 to 24 carbon atoms, deuterium substituted or unsubstituted arylalkyl group having 7 to 24 carbon atoms , deuterium substituted or unsubstituted alkylaryl group having 7 to 24 carbon atoms, deuterium substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, deuterium substituted or unsubstituted heteroarylalkyl group
  • Aryl group deuterium-substituted or unsubstituted alkoxy group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted amine group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted silyl group of 1 to 24 carbon atoms, deuterium-substituted or unsubstituted Any one selected from the group consisting of a germanium group having 1 to 24 carbon atoms, a deuterium-substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, and a deuterium-substituted or unsubstituted arylthionyl group having 6 to 24 carbon atoms,
  • R 11 to R 16 in the structural formula A When Q in the structural formula A is structural formula Q-2, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-2 One of R 25 to R 34 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
  • R 11 to R 16 in the structural formula A When Q in the structural formula A is structural formula Q-3, one of R 11 to R 16 in the structural formula A, or Within structural formula Q-3 One of R 35 to R 42 is a single bond bonded to the carbon atom or nitrogen atom bonded to R 1 to R 3 ,
  • R 43 and R 44 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  • the substituent represented by [Structural Formula A] may be any one of the substituents selected from the following [Structural Formula A-1] to [Structural Formula A-15].
  • At least one of R 1 to R 3 in [Formula A] and [Formula B] may be a substituent represented by [Structural Formula A], and more preferably, only R 2 It may be a substituent represented by [structural formula A], or only R 3 may be a substituent represented by [structural formula A].
  • the substituent R 1 in Formula A and Formula B may be any one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted phenanthryl group. there is.
  • aromatic heterocyclic compound represented by [Formula A] or [Formula B] of the present invention it may be any one compound selected from ⁇ 1> to ⁇ 240> below, but is not limited thereto. No.
  • the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes one or more compounds represented by [Formula A] or [Formula B] according to the present invention.
  • the organic light emitting device according to the present invention can exhibit low voltage driving, high efficiency, and long life characteristics.
  • the organic layer includes one or more organic compounds
  • the organic layer in the organic light emitting device of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer, At least one of the organic layers may include one or more aromatic heterocyclic compounds represented by [Formula A] or [Formula B].
  • the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes: a light emitting layer; And, at least one layer of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and the light emitting layer is a host. and a dopant, and the host provides an organic light-emitting device including one or more of the aromatic heterocyclic compounds according to the present invention.
  • a dopant material may be used in the light emitting layer in addition to a host.
  • the content of the dopant can typically be selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
  • the dopant is not a fluorescent dopant material that only transitions to a singlet state using the Forster energy transfer method in the existing host-dopant system, but a singlet dopant material.
  • Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re using the Dexter Energy transfer method that transfers without distinguishing between and triplet states.
  • It includes a phosphorescent dopant material of a metal complex containing one or more metals selected from Pd, etc., and known dopant materials can be used without particular restrictions as long as they emit light from triplet excitons.
  • Ir, Pt, Pd, etc. can be selected as the metal complex, and specific examples include Ir(ppy) 3 , Ir(ppy) 2 acac, Ir(Bt) 2 acac, Ir(MDQ) 2 acac, Ir( mppy) 3 , Ir(piq) 3, Ir (piq) 2 acac, Ir (pq) 2 acac, Ir(mpp) 2 acac, F 2 Irpic, (F 2 ppy) 2 Ir(tmd), Ir(ppy) 2 tmd, Ir(pmi) 3 , Ir(pmb) 3 , FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir(chpy) 3 ,P0-01(C 31 H 23 IrN 2 O 2 S 2 ), Ir (ppz) 3, Ir(dfppz) 3, PtNON, Pt-10,
  • PtOEP Ir(Bt) 2 acac, Ir(MDQ) 2 acac, Ir(piq) 3 , Ir(piq) 2 acac, Ir(pq) 2 acac used as a red phosphorescent dopant. etc. may be used, but are not limited thereto.
  • the organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, and the host in the light-emitting layer is represented by [Formula A] or [Formula B].
  • the host in the light-emitting layer is represented by [Formula A] or [Formula B].
  • one or more additional host compounds may be included, and two or more types of host compounds may be mixed or stacked.
  • one or more additional host compounds are additionally included, and when two or more host compounds are used mixed or stacked, more preferably As the additional host, a compound having an electron accepting moiety may be used, Due to the high hole injection caused by mixing or stacking with [Formula A] or [Formula B] having an amine group, which is an electron donor moiety, and the HOMO/LUMO level of the electron injection barrier, the recombination area is limited to the interface of the two hosts, thereby reducing current loss. Due to the advantages of minimizing high efficiency and long lifespan, organic light emitting devices can be implemented.
  • compounds having the electron accepting moiety receive electrons from the outside, such as azine compounds, which are nitrogen-containing aromatic heterocycles such as pyridine, pyrimidine, and triazine, and compounds substituted with a cyano group (-CN) in the molecule.
  • a compound having a moiety that has an environment that is easy to receive Preferably a heteroaryl group containing 1 to 3 N (nitrogen) elements in the molecule; Alternatively, it may include a compound containing an aryl group containing 1 to 3 cyano groups (-CN) in the molecule.
  • the light emitting layer may further include various hosts and various dopant materials in addition to the dopant and host.
  • FIG. 1 is a diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.
  • the organic light emitting device includes an anode 20, a hole transport layer 40, a light emitting layer 50 including a host and a dopant, an electron transport layer 60, and a cathode ( 80) in sequential order, wherein the anode is a first electrode, the cathode is a second electrode, a hole transport layer is provided between the anode and the light-emitting layer, and an electron transport layer is provided between the light-emitting layer and the cathode. Applies to organic light emitting devices.
  • the organic light emitting device includes a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron transport layer 60 and the cathode 80.
  • An injection layer 70 may be included.
  • the organic light-emitting device of the present invention and its manufacturing method will be described with reference to FIG. 1 as follows.
  • the positive electrode (anode) material is coated on the upper part of the substrate 10 to form the positive electrode 20.
  • the substrate 10 a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable.
  • the hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on the upper electrode of the anode 20.
  • a hole transport layer 40 is formed on the top of the hole injection layer 30 by vacuum thermal evaporation or spin coating of a hole transport layer material.
  • the hole injection layer material can be used without particular restrictions as long as it is commonly used in the industry, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] can be used, etc.
  • 2-TNATA 4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine]
  • NPD
  • the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl -[1,1- Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD) can be used.
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl -[1,1- Biphenyl]-4,4'-diamine
  • a-NPD N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine
  • the present invention is not necessarily limited thereto.
  • an electron blocking layer may be additionally formed on the hole transport layer.
  • the electron blocking layer is a layer to improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole transport layer, and can be formed in an appropriate portion between the light-emitting layer and the hole injection layer. and may preferably be formed between the light emitting layer and the hole transport layer.
  • the light emitting layer 50 may be laminated on the hole transport layer 40 or the electron blocking layer using a vacuum deposition method or a spin coating method.
  • the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.
  • the thickness of the light-emitting layer is preferably 50 to 2,000 ⁇ .
  • a thin film of a hole blocking layer (not shown) can be selectively formed on the organic light emitting layer 50 using a vacuum deposition method or a spin coating method.
  • the hole blocking layer serves to prevent this problem by using a material with a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the light emitting layer and flow into the cathode.
  • the hole blocking material used is not particularly limited, but must have electron transport ability and a higher ionization potential than the light-emitting compound.
  • Materials used in the hole blocking layer include BAlq, BCP, Bphen, TPBI, NTAZ, BeBq 2 , OXD-7, Liq and any one selected from Formulas 1001 to 1007 may be used, but are not limited thereto.
  • the electron transport layer 60 is deposited on the light emitting layer or the hole blocking layer through a vacuum deposition method or a spin coating method.
  • a known electron transport material that functions to stably transport electrons injected from an electron injection electrode (cathode) can be used.
  • known electron transport materials include quinoline derivatives, especially tris(8-quinolinolate) aluminum (Alq 3 ), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) Materials such as -10-olate: Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, and BND may be used, but are not limited thereto.
  • an electron injection layer which is a material that has the function of facilitating injection of electrons from the cathode, can be laminated on the top of the electron transport layer. This is a special material. No restrictions.
  • any material known as an electron injection layer forming material such as CsF, NaF, LiF, Li 2 O, BaO, etc. can be used.
  • the deposition conditions for the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions that are substantially the same as those for forming the hole injection layer.
  • the thickness of the electron injection layer may be about 1 ⁇ to about 100 ⁇ , or about 3 ⁇ to about 90 ⁇ . When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
  • the cathode may be made of a material with a low work function to facilitate electron injection.
  • Lithium (Li), magnesium (Mg), calcium (Ca), or their alloys aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) etc., or a transmission type cathode using ITO or IZO can be used.
  • the organic light-emitting device of the present invention may additionally include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material that emits light in a wavelength range of 380 nm to 800 nm. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the blue light-emitting material, green light-emitting material, or red light-emitting material in the additionally formed light-emitting layer may be a fluorescent material or a phosphorescent material.
  • one or more layers selected from among the above layers may be formed by a single molecule deposition process or a solution process.
  • the deposition process refers to a method of forming a thin film by evaporating the material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is used to form each layer.
  • This refers to a method of mixing a substance used as a material with a solvent and forming a thin film through methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating.
  • the organic light emitting device in the present invention may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; and devices for single-color or white flexible lighting; Vehicle display devices; and a display device for virtual or augmented reality.
  • ⁇ B-2> was synthesized in the same manner except that ⁇ B-1> was used instead of ⁇ A-2> used in Synthesis Example 1-3, and ⁇ B-2a> was used instead of ⁇ A-3a>. got it (yield 68.2%)
  • ⁇ C-1a> 100 g of ⁇ C-1a>, 8.4 g of iodine, and 500 mL of pyridine were added to the nitrogen-purged reactor.
  • ⁇ A-1b> 57.9 mL was added dropwise, and the temperature was raised to 80°C. After 3 hours, it was cooled to room temperature, and then saturated sodium thiosulfate aqueous solution and ethyl acetate were added to separate the layers. After concentrating the organic layer under reduced pressure, toluene was added and heated to dissolve, filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain ⁇ C-1>. (128 g, 95.1%)
  • ⁇ G-1> was obtained by synthesis in the same manner, except that ⁇ G-1a> was used instead of ⁇ A-2> used in Synthesis Example 1-3. (yield 95.2%)
  • ⁇ G-4> was synthesized in the same manner except that ⁇ G-3> was used instead of ⁇ A-4> used in Synthesis Example 1-5, and ⁇ G-4a> was used instead of ⁇ A-5a>. got it (yield 65.2%)
  • ⁇ G-7> was obtained by synthesis in the same manner, except that ⁇ G-6> was used instead of ⁇ A-3> used in Synthesis Example 1-4. (yield 30.5%)
  • the ITO glass was patterned so that the light emitting area was 2 mm ⁇ 2 mm in size and then cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure is set to 1 ⁇ 10 -6 torr, and then HATCN (50 ⁇ ) and NPD (1500 ⁇ ) are formed on the ITO in that order.
  • the organic light emitting device for the comparative example was manufactured in the same manner as the device structure of the above example, except for the following [RH-1] and [RH-2] instead of the compound according to the present invention as the host compound.
  • the emission characteristics of the organic light emitting device were measured at 0.4 mA.
  • the structures of [RH-1] and [RH-2] are as follows.
  • the organic light-emitting compound according to the present invention appears to have better low-voltage driving, high efficiency, and long life characteristics compared to Comparative Examples 1 and 2 according to the prior art. It shows high applicability as a light-emitting device.
  • the aromatic heterocyclic compound represented by [Formula A] or [Formula A] according to the present invention When used as a phosphorescent host material for a light-emitting layer in an organic light-emitting device, it operates at a lower voltage and has higher efficiency than the organic light-emitting device according to the prior art. and long lifespan, it has high industrial applicability in industrial fields such as organic light-emitting devices and displays.

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Abstract

La présente invention concerne : un nouveau composé hétérocyclique aromatique qui peut être utilisé dans une diode électroluminescente organique ; et une diode électroluminescente organique le comprenant.
PCT/KR2023/003724 2022-03-23 2023-03-21 Nouveau composé hétérocyclique et diode électroluminescente organique le comprenant WO2023182775A1 (fr)

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KR20220036039 2022-03-23
KR10-2022-0036039 2022-03-23
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KR10-2022-0076756 2022-06-23

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Citations (5)

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WO2014003336A1 (fr) * 2012-06-27 2014-01-03 덕산하이메탈(주) Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé
US20140047976A1 (en) * 2011-04-29 2014-02-20 Yin Fong Yeong Cardo-Polybenzoxazole Polymer/Copolymer Membranes For Improved Permeability And Method For Fabricating The Same
US20160141515A1 (en) * 2013-06-11 2016-05-19 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent elements, organic electroluminescent element using same, and electronic device
US20170346018A1 (en) * 2015-03-13 2017-11-30 Fujifilm Corporation Composition for forming organic semiconductor film, organic thin film transistor, electronic paper, and display device
KR20210006283A (ko) * 2019-07-08 2021-01-18 롬엔드하스전자재료코리아유한회사 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160143678A (ko) 2014-04-22 2016-12-14 유니버셜 디스플레이 코포레이션 인광 발광성 소자용 물질
WO2015178732A1 (fr) 2014-05-23 2015-11-26 Rohm And Haas Electronic Materials Korea Ltd. Matériau hôte multi-composant et dispositif électroluminescent organique le contenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140047976A1 (en) * 2011-04-29 2014-02-20 Yin Fong Yeong Cardo-Polybenzoxazole Polymer/Copolymer Membranes For Improved Permeability And Method For Fabricating The Same
WO2014003336A1 (fr) * 2012-06-27 2014-01-03 덕산하이메탈(주) Composé, dispositif électro-organique utilisant ce composé, et dispositif électronique ainsi réalisé
US20160141515A1 (en) * 2013-06-11 2016-05-19 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent elements, organic electroluminescent element using same, and electronic device
US20170346018A1 (en) * 2015-03-13 2017-11-30 Fujifilm Corporation Composition for forming organic semiconductor film, organic thin film transistor, electronic paper, and display device
KR20210006283A (ko) * 2019-07-08 2021-01-18 롬엔드하스전자재료코리아유한회사 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자

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