WO2021150090A1 - Organic light-emitting element - Google Patents

Organic light-emitting element Download PDF

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WO2021150090A1
WO2021150090A1 PCT/KR2021/095005 KR2021095005W WO2021150090A1 WO 2021150090 A1 WO2021150090 A1 WO 2021150090A1 KR 2021095005 W KR2021095005 W KR 2021095005W WO 2021150090 A1 WO2021150090 A1 WO 2021150090A1
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group
substituted
unsubstituted
light emitting
formula
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PCT/KR2021/095005
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French (fr)
Korean (ko)
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하재승
홍완표
이호중
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주식회사 엘지화학
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Priority to CN202180003753.6A priority Critical patent/CN113950754B/en
Publication of WO2021150090A1 publication Critical patent/WO2021150090A1/en

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    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides an organic light emitting device.
  • One embodiment of the present specification is an anode; cathode; a light emitting layer provided between the anode and the cathode; and a hole transport region including two or more organic material layers provided between the light emitting layer and the anode, wherein the organic material layer in contact with the light emitting layer among the organic material layers contains a compound represented by the following formula (1), and the light emitting layer comprises:
  • An organic light emitting device including a compound represented by the following formula (2) is provided.
  • R8 and R9 is a group represented by the following formula (a), and among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring can form,
  • Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • the 2 or more L1s are the same as or different from each other,
  • the 2 or more L2s are the same as or different from each other,
  • the 2 or more L3 are the same as or different from each other,
  • At least one of G1 to G10 is a group represented by the following formula (b), the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a and B are the same as or different from each other and a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring,
  • L4 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • l4 is an integer from 1 to 3
  • the 2 or more L4s are the same as or different from each other,
  • the deuterium substitution rate of Formula 2 is 40% to 100%.
  • the organic light emitting device includes the compound of Formula 1 in the organic material layer in contact with the emission layer and the compound of Formula 2 in the emission layer, so that the driving voltage is low, the light efficiency is improved, and the thermal stability of the compound This can improve the lifespan characteristics of the device.
  • 1 to 4 show examples of an organic light emitting device according to an exemplary embodiment of the present specification.
  • X% deuterated means that X% of hydrogens at substitutable positions in the structure are replaced with deuterium.
  • the dibenzofuran is “25% deuterated”
  • the “degree of deuterium 25%” of the dibenzofuran, or the “deuterium substitution rate of 25%” of the dibenzofuran is It means that 2 out of 8 hydrogens at substitutable positions of dibenzofuran are substituted with deuterium.
  • degree of deuteration or “deuterium substitution rate” is nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry), etc. can be confirmed by a known method.
  • the substitution rate is determined based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. can be calculated For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506, and the maximum molecular weight (median value) of the following compound A in the MS graph of FIG. 5 is 527. Since 21 of the 26 hydrogens at the positions have been replaced with deuterium, it can be calculated that about 81% of the hydrogens are deuterated.
  • the 'layer' means compatible with the 'film' mainly used in the present technical field, and refers to a coating covering a desired area.
  • the size of the 'layers' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.
  • the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.
  • the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more C-layers and one or more D-layers, respectively.
  • condition A or B refers to an inclusive 'or' and does not mean an exclusive 'or'. For example, condition A or B is satisfied by either: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or exists), and both A and B are true (or present).
  • a mixture thereof or “mixture” means that two or more kinds of substances are included.
  • the “mixture” or “mixture” may include, but is not limited to, a uniformly and/or non-uniformly mixed state, a dissolved state, a uniformly and/or non-uniformly dispersed state, and the like.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more substituted , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; hydroxyl group; cyano group; nitro group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
  • that two or more substituents are connected means that hydrogen of any one substituent is connected with another substituent.
  • a phenyl group and a naphthyl group are connected. or may be a substituent of
  • the connection of three substituents means that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, as well as (substituent 2) and (substituent 3) are connected to (substituent 1).
  • a phenyl group, a naphthyl group and an isopropyl group are connected, , or may be a substituent of The above definition applies equally to the case where 4 or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl,
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.
  • heteroaryl group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group.
  • pyridazine group pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenoc
  • the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like.
  • Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group
  • the examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group
  • the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the boron group includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
  • the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group.
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the alkyl group and the aryl group in the N-alkylarylamine group are the same as the above-described alkyl group and aryl group.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heteroaryl group.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-described alkyl group and heteroaryl group.
  • examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group.
  • the alkyl group in the alkylamine group may be a straight-chain or branched alkyl group.
  • the alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched alkyl group at the same time.
  • the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or the aryl group, except for those not monovalent.
  • the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms.
  • the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.
  • An organic light emitting device includes an anode; cathode; a light emitting layer provided between the anode and the cathode; and a hole transport region including two or more organic material layers provided between the light emitting layer and the anode, wherein the organic material layer in contact with the light emitting layer among the organic material layers contains a compound represented by the following formula (1), and the light emitting layer comprises: It includes a compound represented by the following formula (2).
  • the deuterium substitution rate of the compound of Formula 2 is 40% to 100%.
  • the organic light-emitting device includes the compound of Formula 1 between the anode and the emission layer, that is, in the hole transport region, and the compound of Formula 2 is included in the emission layer.
  • the compound of Formula 1 in the hole transport region of the organic light emitting device, injection and transport of holes can be accelerated and carrier transport into the light emitting layer can be maximized to increase the efficiency of the light emitting layer, and by including the compound of Formula 2 in the light emitting layer , it is possible to obtain a device having an excellent lifespan.
  • the deuterium substitution rate of Formula 2 is 40% to 100%, preferably 40% to 99%.
  • the deuterium substitution rate of Formula 2 is 45% to 100%.
  • the deuterium substitution rate of Formula 2 is 50% to 100%.
  • the deuterium substitution rate of Formula 2 is 65% to 100%.
  • the deuterium substitution rate of Formula 2 is 80% to 100%.
  • the deuterium substitution rate of Formula 2 is 90% to 100%.
  • the deuterium substitution rate of Formula 2 is 100%.
  • the organic light emitting device including the compound of Formula 2 having a deuterium substitution rate according to an exemplary embodiment of the present specification has an effect of improving the device lifespan.
  • the deuterium substitution rate of Formula 1 is 1% to 100%.
  • At least one of the hydrogens in the substitutable positions of Formula 1 is substituted with deuterium.
  • a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other and have 6 to 20 substituted or unsubstituted carbon atoms to form an aromatic hydrocarbon ring.
  • a group other than the group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a benzene ring.
  • R1 and R18 are bonded to each other to form a substituted or unsubstituted fluorene ring.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • R2 to R17, R101 and R118 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • L1 to L3, 11 to 13, Ar1 and Ar2 are the same as those defined in Formula (a) above.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C10 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; an alkyl group; Or an aryl group unsubstituted or substituted with deuterium.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium.
  • R8 and R9 a group other than a group represented by the following formula (a), R1 to R7, R11 and R13 to R18 are hydrogen.
  • R12 is hydrogen; tert-butyl group; or a phenyl group.
  • R1 to R6 and R12 to R18 are hydrogen.
  • R7 is a phenyl group substituted with deuterium.
  • l1 is 1.
  • l1 is 2.
  • l2 is 1.
  • l3 is 1.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; an arylene group unsubstituted or substituted with one or more selected from deuterium, an alkyl group, and an aryl group; or a heteroarylene group unsubstituted or substituted with deuterium or an alkyl group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms which is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 20 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; a divalent fluorene group substituted with one or more selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a divalent benzofuran group unsubstituted or substituted with deuterium.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; a divalent fluorene group substituted with one or more selected from deuterium, a methyl group, and a phenyl group; or a divalent benzofuran group unsubstituted or substituted with deuterium.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; biphenylrylene group; terphenylrylene group; a divalent fluorene group substituted with one or more selected from a methyl group and a phenyl group; or a divalent benzofuran group.
  • L1 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.
  • L1 is a direct bond; an arylene group unsubstituted or substituted with deuterium; or a heteroarylene group.
  • L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.
  • L1 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; or a divalent benzofuran group.
  • L1 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; biphenylrylene group; or a divalent benzofuran group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; or an arylene group unsubstituted or substituted with one or more selected from deuterium, an alkyl group, and an aryl group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. .
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. .
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; or a divalent fluorene group substituted with one or more selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; or a divalent fluorene group substituted with one or more selected from deuterium, a methyl group, and a phenyl group.
  • L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; biphenylrylene group; terphenylrylene group; or a divalent fluorene group substituted with one or more selected from a methyl group and a phenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a straight or branched chain having 1 to 30 carbon atoms substituted with deuterium
  • a monocyclic or polycyclic aryl having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from an alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a straight or branched chain having 1 to 30 carbon atoms substituted with deuterium a phenyl group unsubstituted or substituted with one or more selected from an alkyl group and a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a biphenyl group unsubstituted or substituted with one or more selected from deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms; terphenyl group; quarter phenyl group; a naphthyl group unsubstituted or substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; triphenylene group; Deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more selected from deuterium, tert-butyl group, trimethylsilyl group, methyl group and phenyl group; a biphenyl group unsubstituted or substituted with one or more selected from deuterium, and a tert-butyl group; terphenyl group; quarter phenyl group; a naphthyl group unsubstituted or substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; triphenylene group; a fluorene group substituted with one or more selected from deuterium, a trituterium methyl group, a methyl group, and a phenyl group; a carbazole group; dibenzofuran group; a benzofuran group unsubstituted or
  • R101 and R118 are hydrogen.
  • At least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted aryl group.
  • At least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • At least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more selected from a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium.
  • At least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with one or more selected from monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium; a naphthyl group unsubstituted or substituted with one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; a biphenyl group unsubstituted or substituted with one or more selected from monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium; a terphenyl group substituted with deuterium; a phenanthrene
  • At least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group substituted or unsubstituted with one or more selected from a phenyl group substituted or unsubstituted with deuterium, a phenyl group unsubstituted or substituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with one or more selected from deuterium, deuterium, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with deuteruter
  • G1 is a group represented by Formula b.
  • G3 is a group represented by Formula b.
  • G1 and G6 are the same as or different from each other, and are each a group represented by Formula b.
  • 14 is 1.
  • L4 is a direct bond; or a substituted or unsubstituted arylene group.
  • L4 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L4 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L4 is a direct bond; or a substituted or unsubstituted arylene group.
  • L4 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • L4 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • L4 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
  • a and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring.
  • a and B are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
  • a and B are the same as or different from each other, and each independently at least one selected from a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium. a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • a and B are the same as or different from each other, and each independently at least one selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.
  • a substituted or unsubstituted benzene ring a naphthalene ring unsubstituted or substituted with deuterium; a phenanthrene ring unsubstituted or substituted with deuterium; a triphenylene ring unsubstituted or substituted with deuterium; Or a dibenzofuran ring unsubstituted or substituted with deuterium.
  • Formula 1 is any one selected from the following compounds.
  • Formula 2 is any one selected from the following compounds.
  • the organic material layer in contact with the anode among the organic material layer includes a carbazole-based compound.
  • the carbazole-based compound may be represented by the following structural formula, but is not limited thereto.
  • t1 is an integer of 1 to 4, and when t1 is 2 or more, T1 of 2 or more are the same as or different from each other,
  • t2 is an integer of 1 to 4, and when t2 is 2 or more, T2 or more are the same as or different from each other,
  • t3 is an integer of 1 to 10, and when t3 is 2 or more, T3 of 2 or more are the same as or different from each other.
  • the carbazole-based compound may be selected from the following compounds, but is not limited thereto.
  • the organic material layer includes a hole transport layer and a hole control layer
  • the hole transport layer includes a compound represented by Formula 1 above.
  • the organic material layer includes a hole transport layer and a hole control layer
  • the hole control layer includes a compound represented by Formula 1 above.
  • a hole transport region including the hole transport layer and the hole control layer is included between the anode and the light emitting layer, and the hole transport layer and the hole control layer are provided in contact with each other.
  • the hole control layer is provided in contact with the light emitting layer.
  • the structure of the organic light emitting device of the present specification may have, for example, the structure shown in FIGS. 1 to 4 , but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device in which an anode 2, a hole transport region 3, a light emitting layer 4, and a cathode 5 are sequentially stacked on a substrate 1 .
  • 1 is an exemplary structure according to an embodiment of the present specification, and may further include another organic material layer.
  • 3 shows an anode 2, a hole injection layer 6, a hole transport region 3, a light emitting layer 4, an electron transport region 7, an electron injection layer 8 and a cathode 5 on the substrate 1
  • a structure of an organic light emitting device in which is sequentially stacked is illustrated.
  • 3 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • the thickness of the hole transport layer is 50 nm to 200 nm.
  • the hole transport region is composed of a plurality or a single layer including a hole transport layer and a hole control layer, and the thickness of the hole transport region can be determined based on an optimum point within the thickness in order to optimize the optical properties of the organic light emitting device. .
  • a layer including Formula 1 has the triplet energy range, it is common to exhibit a relatively high singlet energy, and thus a low It is common to have the highest occupied orbital energy. Therefore, since carrier and exciton movement or transition in the light emitting layer is not easy, the efficiency of the fabricated organic light emitting device can be improved and stability can be derived.
  • the highest occupied molecular orbital refers to a molecular orbital (highest occupied molecular orbital) in the region with the highest energy in the region where electrons can participate in bonding
  • the lowest unoccupied molecular orbital is the molecular orbital function (lowest unoccupied molecular orbital) in which electrons are in the lowest energy region among the anti-bonding regions
  • the HOMO energy level means the distance from the vacuum level to the HOMO.
  • the LUMO energy level means the distance from the vacuum level to the LUMO.
  • Biovia's 'DMol3' package can be used to perform calculations using the full-density function method. If the optimal molecular structure is determined using the method given above, the energy level that electrons can occupy can be obtained as a result.
  • triplet energy refers to an electronic state in which the spin quantum number is 1 in a molecule.
  • the triplet energy is the energy level of a singlet and a triplet using a time dependent density functional theory (TD-DFT) to obtain the properties of an excited state with respect to the optimal molecular structure determined by the above method.
  • the general density function calculation can be performed using the 'Gaussian09' package, a commercial calculation program developed by Gaussian.
  • the B3PW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and the 6-31G* basis set are used to calculate the time-dependent universal density function.
  • the 6-31G* basis set is described in the paper 'J. A. Pople et al., J. Chem. Phys. 56, 2257 (1972)'.
  • the energy when the electron arrangement is singlet and triplet is calculated using the time-dependent universal density function method (TD-DFT).
  • the light emitting layer includes a host and a dopant.
  • the organic light emitting device is a blue organic light emitting device.
  • At least one of the two or more types of mixed hosts includes a compound represented by Formula 2, and the rest may be used without limitation as long as it is an anthracene-based host used in the art if it is different from Formula 2 above, limited only to this it's not going to be
  • the organic light emitting device has a maximum emission wavelength ( ⁇ max ) of an emission spectrum of 400 nm to 470 nm.
  • the pyrene-based compound and the non-pyrene-based compound may be used without limitation as long as they are compounds used in the art, but are not limited thereto.
  • the non-pyrene-based compound includes a boron-based compound.
  • the organic light emitting device includes an electron transport region provided between the cathode and the light emitting layer.
  • X1 is N or Q101
  • X2 is N or Q102
  • X3 is N or Q103
  • At least one of X1 to X3 is N,
  • Q101 to Q103 and Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • the electron transport region may be used without limitation as long as it is a monocyclic 6-membered heterocyclic compound, that is, a triazine-based derivative, a pyrimidine-based derivative, and a pyridine-based derivative, but is not limited thereto.
  • the electron transport region includes a compound represented by Chemical Formula 3, an organic alkali metal complex, and a mixture thereof.
  • the organic alkali metal complex may be lithium quinolate or aluminum quinolate, but is not limited thereto, and the content of the organic alkali metal complex is 10 to 90 wt%, preferably 30 to 70 wt%, based on the material of the organic layer. included in %.
  • the electron transport region includes an electron transport layer and an electron control layer.
  • the organic light emitting device may further include an additional organic material layer.
  • the additional organic material layer includes at least one of a light emitting layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron control layer, an electron blocking layer, a hole blocking layer, and a hole control layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification is known in the art, except that the layer adjacent to the light emitting layer of the organic material layer includes the compound represented by Formula 1, and the light emitting layer includes the compound represented by Formula 2 It can be manufactured with materials and methods.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate.
  • PVD physical vapor deposition
  • It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Laid-Open No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • anode material a material having a large work function is generally preferable to facilitate hole injection into the organic material layer.
  • the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF/Al or LiO 2 /Al, and a multi-layered material such as Mg/Ag, but is not limited thereto.
  • a capping layer for protecting the electrode may be additionally formed on the cathode, and materials used in the art may be appropriately used for the capping layer material.
  • the hole injection layer is a layer for injecting holes from the electrode as a hole injection material, and has an ability to transport holes as a hole injection material, so that it has an excellent hole injection effect with respect to the hole injection effect at the anode, the light emitting layer or the light emitting material.
  • a compound that prevents the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer.
  • the hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them to the light emitting layer. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the electron blocking layer is a layer that can improve the life and efficiency of the device by preventing the holes injected from the hole injection layer from entering the electron injection layer through the emission layer. It may be formed in an appropriate portion between.
  • the light emitting material of the light emitting layer is a material capable of emitting light in the visible ray region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and the organic light emitting device of the present specification includes a compound represented by Formula 2
  • a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but is not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compounds
  • compounds of the benzoxazole, benzothiazole and benzimidazole series Poly(p-phenylenevinylene) (PPV)-based polymers
  • spiro compounds polyfluorene, rubrene, etc., but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material includes a condensed aromatic ring derivative or a compound containing a hetero ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic compound containing carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • An electron control layer may be further provided between the light emitting layer and the electron transport layer.
  • the material for the electron control layer any material used in the art may be appropriately used.
  • the electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer, and the electron transport material is a material that can receive electrons from the cathode and transfer them to the light emitting layer.
  • Materials with high mobility are suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer may be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.
  • the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer.
  • a compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc.
  • the present invention is not limited thereto.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.
  • the organic light emitting device may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • the structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.
  • Each product had a different degree of deuterium substitution depending on the reaction time, and the substitution rate was determined according to the maximum m/z (M+) value.
  • Each product had a different degree of deuterium substitution depending on the reaction time, and the substitution rate was determined according to the maximum m/z (M+) value.
  • a substrate on which 70/1000/70 ⁇ of ITO/Ag/ITO was deposited as an anode was cut into a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves.
  • the detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.
  • HI-1 was thermally vacuum deposited to a thickness of 50 ⁇ to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 ⁇ to form a hole transport layer.
  • a hole control layer was formed using EB1 (150 ⁇ ), and then BH1 and a dopant BD1 (2 wt %) were vacuum-deposited to a thickness of 360 ⁇ to form a light emitting layer.
  • HB1 was deposited by 50 ⁇ to form an electron control layer, and the compound ET1 and Liq were mixed at 5:5 (mass ratio) to form an electron transport layer having a thickness of 250 ⁇ .
  • Comparative Example 1-1 The same as in Comparative Example 1-1, except that in Comparative Example 1-1, the compound of Table 3 was used instead of BH1 as the host of the light emitting layer, and the compound of Table 3 was used instead of EB1 as the hole control layer.
  • the organic light emitting device was prepared in the above-mentioned manner, and the structures of the organic light emitting devices prepared in Comparative Examples 1-1 to 1-15 and Examples 1-1 to 1-43 are shown in Table 3 below, and Table 4 below is shown in the comparative examples.
  • Examples 1-1 to 1-15 and Examples 1-1 to 1-43 are the results of measuring the driving voltage, luminous efficiency, and time (LT95) to 95% of the initial luminance at a current density of 20 mA/cm 2 .
  • the organic light emitting device according to an exemplary embodiment of the present specification is a light emitting layer by using the compound of Formula 1 applied to the hole transport region of the blue organic light emitting device and Formula 2 applied as a host of the light emitting layer. showed excellent hole injection and transport ability.
  • the organic light emitting device according to the present specification exhibits superior characteristics in terms of efficiency, driving voltage, and stability than the organic light emitting device including Formula 1 or Formula 2, respectively. It was.
  • the results of the device characteristics according to the deuterium substitution rate of Formula 2 can also be observed by looking at the results of Tables 3 to 4.
  • a substrate on which 70/1000/70 ⁇ of ITO/Ag/ITO was deposited as an anode was cut into a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves.
  • the detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.
  • HI-1 was thermally vacuum deposited to a thickness of 50 ⁇ to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 ⁇ to form a hole transport layer.
  • a hole control layer was formed using EB1 (150 ⁇ ), and then BH1 and dopant BD2 (2 wt %) were vacuum-deposited to a thickness of 360 ⁇ to form a light emitting layer.
  • HB1 was deposited by 50 ⁇ to form an electron control layer, and the compound ET1 and Liq were mixed at 5:5 (mass ratio) to form an electron transport layer having a thickness of 250 ⁇ .
  • Comparative Example 2-1 The same as in Comparative Example 2-1, except that in Comparative Example 2-1, the compound of Table 5 was used instead of BH1 as the host of the light emitting layer, and the compound of Table 5 was used instead of EB1 as the hole control layer.
  • the organic light emitting diodes were prepared in the above manner, and the structures of the organic light emitting diodes prepared in Comparative Examples 2-1 to 2-10 and Examples 2-1 to 2-41 are shown in Table 5 below, and Table 6 below is Examples 2-1 to 2-10 and Examples 2-1 to 2-41 at a current density of 20 mA/cm 2
  • the driving voltage, luminous efficiency, and time (LT95) to be 95% compared to the initial luminance are measured results .
  • the organic light emitting device according to an exemplary embodiment of the present specification is a light emitting layer by using the compound of Formula 1 applied to the hole transport region of the blue organic light emitting device and Formula 2 applied as a host of the light emitting layer. showed excellent hole injection and transport ability.
  • the organic light emitting device according to the present specification exhibits superior characteristics in terms of efficiency, driving voltage, and stability than the organic light emitting device including Formula 1 or Formula 2, respectively. It was.
  • the device configuration shows that BD1 or BD2 of various hole control layers corresponding to Chemical Formula 1 and various blue hosts and blue fluorescent dopants corresponding to Chemical Formula 2 can be applied.
  • Examples 1-39 to 1-41 and 2-39 to 2-41 show that two types of hosts corresponding to Formula 2 are used as mixed hosts to improve device performance.
  • Comparative Examples 1-1 to 1-6, 1-11 to 1-13, and 2-1 to 2-6 are results of devices manufactured with compounds other than the combination of compounds 1 and 2 according to an exemplary embodiment of the present specification and an aryl-based anthracene was used as the host of the light emitting layer. In all of these cases, high voltage, low efficiency, and low lifetime indicate poor performance of the device.
  • Comparative Examples 1-7, 1-8, 1-14, 1-15, 2-7, and 2-8 are the results of applying only the hole control layer corresponding to Chemical Formula 1, and Comparative Examples 1-1 to 1-6, It can be seen that a slight decrease in driving voltage compared to 1-11 to 1-13 and 2-1 to 2-6 can be observed, but overall device performance is not improved.
  • Comparative Examples 1-9, 1-10, 2-9 and 2-10 are the results of applying only the blue host corresponding to Chemical Formula 2, and Comparative Examples 1-1 to 1-6, 1-11 to 1- 13 and 2-1 to 2-6 compared to the overall lifespan can be observed.
  • Examples 1-1 to 1-43 and 2-1 to 2-41 are a combination of Chemical Formulas 1 and 2 of the present specification, and the carrier of the device , in particular, it is easy to inject holes into the host, so it plays a role in balancing the device and shows that the overall performance of the device can be improved.
  • Examples 2-1 to 2-41 it was observed that the device balance of the corresponding combination was excellent even when various types of blue dopants were introduced as a result of the device to which the combination of BD2 and Formulas 1 and 2 of the present specification was applied can do.

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Abstract

The present application relates to an organic light-emitting element comprising: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; and a hole transport region including two or more organic material layers provided between the light-emitting layer and the anode, wherein from among the organic material layers, an organic material layer in contact with the light-emitting layer comprises a compound of chemical formula 1, and the light-emitting layer comprises a compound of chemical formula 2.

Description

유기 발광 소자organic light emitting device
본 출원은 2020년 1월 20일에 한국특허청에 제출된 한국 특허 출원 제 10-2020-0007105호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0007105 filed with the Korean Intellectual Property Office on January 20, 2020, the entire contents of which are incorporated herein by reference.
본 명세서는 유기 발광 소자에 관한 것이다.The present specification relates to an organic light emitting device.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.The development of new materials for the organic light emitting device as described above is continuously required.
본 명세서는 유기 발광 소자를 제공한다.The present specification provides an organic light emitting device.
본 명세서의 일 실시상태는 애노드; 캐소드; 상기 애노드와 상기 캐소드 사이에 구비된 발광층; 및 상기 발광층과 상기 애노드 사이에 구비된 2층 이상의 유기물층을 포함하는 정공수송영역을 포함하는 유기 발광 소자로서, 상기 유기물층 중 발광층에 접하는 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고, 상기 발광층은 하기 화학식 2로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다.One embodiment of the present specification is an anode; cathode; a light emitting layer provided between the anode and the cathode; and a hole transport region including two or more organic material layers provided between the light emitting layer and the anode, wherein the organic material layer in contact with the light emitting layer among the organic material layers contains a compound represented by the following formula (1), and the light emitting layer comprises: An organic light emitting device including a compound represented by the following formula (2) is provided.
[화학식 1][Formula 1]
Figure PCTKR2021095005-appb-img-000001
Figure PCTKR2021095005-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
R8 및 R9 중 어느 하나는 하기 화학식 a로 표시되는 기이고, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 치환 또는 비치환된 탄화수소고리를 형성할 수 있으며,Any one of R8 and R9 is a group represented by the following formula (a), and among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring can form,
[화학식 a][Formula a]
Figure PCTKR2021095005-appb-img-000002
Figure PCTKR2021095005-appb-img-000002
상기 화학식 a에 있어서,In the formula (a),
L1 내지 L3는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
l1 내지 l3는 각각 1 내지 3의 정수이고,l1 to l3 are each an integer of 1 to 3,
상기 l1이 2 이상인 경우, 상기 2 이상의 L1은 서로 같거나 상이하며,When the l1 is 2 or more, the 2 or more L1s are the same as or different from each other,
상기 l2가 2 이상인 경우, 상기 2 이상의 L2는 서로 같거나 상이하고,When the l2 is 2 or more, the 2 or more L2s are the same as or different from each other,
상기 l3가 2 이상인 경우, 상기 2 이상의 L3는 서로 같거나 상이하며,When the l3 is 2 or more, the 2 or more L3 are the same as or different from each other,
Figure PCTKR2021095005-appb-img-000003
는 상기 화학식 1의 R8 또는 R9에 결합되는 부위를 의미하고,
Figure PCTKR2021095005-appb-img-000003
means a site bonded to R8 or R9 of Formula 1,
[화학식 2][Formula 2]
Figure PCTKR2021095005-appb-img-000004
Figure PCTKR2021095005-appb-img-000004
상기 화학식 2에 있어서,In Formula 2,
G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,At least one of G1 to G10 is a group represented by the following formula (b), the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
[화학식 b][Formula b]
Figure PCTKR2021095005-appb-img-000005
Figure PCTKR2021095005-appb-img-000005
상기 화학식 b에 있어서,In the formula (b),
A 및 B는 서로 같거나 상이하고 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리이며,A and B are the same as or different from each other and a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring,
L4는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L4 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
l4는 1 내지 3의 정수이며,l4 is an integer from 1 to 3,
상기 l4가 2 이상인 경우, 상기 2 이상의 L4는 서로 같거나 상이하고,When the l4 is 2 or more, the 2 or more L4s are the same as or different from each other,
Figure PCTKR2021095005-appb-img-000006
는 상기 화학식 2의 G1 내지 G10 중 적어도 하나에 결합되는 부위를 의미하며,
Figure PCTKR2021095005-appb-img-000006
means a site bonded to at least one of G1 to G10 of Formula 2,
상기 화학식 2의 중수소 치환율은 40 % 내지 100%이다.The deuterium substitution rate of Formula 2 is 40% to 100%.
본 명세서의 일 실시상태에 따른 유기 발광 소자는 발광층에 접하는 유기물층에 상기 화학식 1의 화합물을 포함하고, 발광층에 상기 화학식 2의 화합물을 포함하므로 구동전압이 낮고, 광효율이 향상되며, 화합물의 열적안정성에 의하여 소자의 수명특성을 향상시킬 수 있다.The organic light emitting device according to an exemplary embodiment of the present specification includes the compound of Formula 1 in the organic material layer in contact with the emission layer and the compound of Formula 2 in the emission layer, so that the driving voltage is low, the light efficiency is improved, and the thermal stability of the compound This can improve the lifespan characteristics of the device.
도 1 내지 4는 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다.1 to 4 show examples of an organic light emitting device according to an exemplary embodiment of the present specification.
도 5은 화합물 A의 MS 그래프를 나타낸 도이다.5 is a diagram showing an MS graph of Compound A.
[부호의 설명][Explanation of code]
1: 기판1: substrate
2: 애노드2: Anode
3: 정공수송영역3: hole transport area
4: 발광층4: light emitting layer
5: 캐소드5: cathode
3-1: 정공수송층3-1: hole transport layer
3-2: 정공조절층3-2: hole control layer
6: 정공주입층6: hole injection layer
7: 전자수송영역7: Electron transport area
7-1: 전자조절층7-1: electronic control layer
7-2: 전자수송층7-2: electron transport layer
8: 전자주입층8: electron injection layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서에 있어서, "중수소화" 또는 "중수소화된"은 화합물의 치환 가능한 위치의 수소가 중수소로 치환되는 것을 의미한다.As used herein, "deuterated" or "deuterated" means that hydrogen at a substitutable position of a compound is replaced with deuterium.
본 명세서에 있어서, "과중수소화된"은 분자 내 모든 수소가 중수소로 치환된 화합물 또는 기를 의미하고, "100% 중수소화된"과 동일한 의미를 가진다.As used herein, "perdeuterated" refers to a compound or group in which all hydrogens in a molecule are substituted with deuterium, and has the same meaning as "100% deuterated".
본 명세서에 있어서, "X% 중수소화된", "중수소화도 X%", 또는 "중수소 치환율 X%"는 해당 구조에서 치환 가능한 위치의 수소 중 X%가 중수소로 치횐된 것을 의미한다. 예컨대, 해당 구조가 디벤조퓨란인 경우, 상기 디벤조퓨란이 "25% 중수소화된", 상기 디벤조퓨란의 "중수소화도 25%", 또는 상기 디벤조퓨간의 "중수소 치환율 25%"는 상기 디벤조퓨란의 치환 가능한 위치의 8개의 수소 중 2개가 중수소로 치환된 것을 의미한다.In the present specification, "X% deuterated", "deuterated degree X%", or "deuterium substitution rate X%" means that X% of hydrogens at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, the dibenzofuran is "25% deuterated", the "degree of deuterium 25%" of the dibenzofuran, or the "deuterium substitution rate of 25%" of the dibenzofuran is It means that 2 out of 8 hydrogens at substitutable positions of dibenzofuran are substituted with deuterium.
본 명세서에 있어서, "중수소화도" 또는 "중수소 치환율"은 핵자기 공명 분광법( 1H NMR), TLC/MS(Thin-Layer Chromatography/Mass Spectrometry), 또는 GC/MS(Gas Chromatography/Mass Spectrometry) 등의 공지의 방법으로 확인할 수 있다.In the present specification, "degree of deuteration" or "deuterium substitution rate" is nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry), etc. can be confirmed by a known method.
구체적으로, 핵자기 공명 분광법( 1H NMR)으로 "중수소화도" 또는 "중수소 치환율"을 분석하는 경우, Internal standard로 DMF(디메틸포름아마이드)를 첨가하여, 1H NMR 상의 적분(integration) 비율을 통하여, 총 peak의 적분량으로부터 중수소화도 또는 중수소 치환율을 계산 할 수 있다.Specifically, when analyzing "degree of deuteration" or "deuterium substitution rate" by nuclear magnetic resonance spectroscopy ( 1 H NMR), DMF (dimethylformamide) is added as an internal standard, and the integration ratio on 1 H NMR is determined. Through this, the degree of deuterium or deuterium substitution rate can be calculated from the integral amount of the total peak.
또한, TLC/MS(Thin-Layer Chromatography/Mass Spectrometry)를 통하여, "중수소화도" 또는 "중수소 치환율"을 분석하는 경우, 반응 종결 시점에서 분자량들이 이루는 분포의 최대값(중앙값)을 기준으로 치환율을 계산할 수 있다. 예컨대, 하기 화합물 A의 중수소화도를 분석하는 경우, 하기 출발 물질의 분자량이 506이고, 도 5의 MS 그래프에서 하기 화합물 A의 분자량 최대값(중앙값)을 527이라 할 때, 하기 출발 물질의 치환 가능한 위치의 수소(26개) 중 21개가 중수소로 치환되었으므로, 약 81%의 수소가 중수소화되었다고 계산할 수 있다.In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" through TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), the substitution rate is determined based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. can be calculated For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506, and the maximum molecular weight (median value) of the following compound A in the MS graph of FIG. 5 is 527. Since 21 of the 26 hydrogens at the positions have been replaced with deuterium, it can be calculated that about 81% of the hydrogens are deuterated.
Figure PCTKR2021095005-appb-img-000007
Figure PCTKR2021095005-appb-img-000007
본 명세서에 있어서, D는 중수소를 의미한다.In the present specification, D means deuterium.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.
본 명세서에 있어서, 상기 '층'은 본 기술분야에 주로 사용되는 '필름'과 호환되는 의미이며, 목적하는 영역을 덮는 코팅을 의미한다. 상기 '층'의 크기는 한정되지 않으며, 각각의 '층'은 그 크기가 같거나 상이할 수 있다. 일 실시상태에 따르면, '층'의 크기는 전체 소자와 같을 수 있고, 특정 기능성 영역의 크기에 해당할 수 있으며, 단일 서브픽셀(sub-pixel)만큼 작을 수도 있다. In the present specification, the 'layer' means compatible with the 'film' mainly used in the present technical field, and refers to a coating covering a desired area. The size of the 'layers' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.
본 명세서에 있어서, 특정한 A 물질이 B층에 포함된다는 의미는 i) 1종 이상의 A 물질이 하나의 B층에 포함되는 것과 ii) B층이 1층 이상으로 구성되고, A 물질이 다층의 B층 중 1층 이상에 포함되는 것을 모두 포함한다.In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.
본 명세서에 있어서, 특정한 A 물질이 C층 또는 D층에 포함된다는 의미는 i) 1층 이상의 C층 중 1층 이상에 포함되거나, ii) 1층 이상의 D층 중 1층 이상에 포함되거나, iii) 1층 이상의 C층 및 1층 이상의 D층에 각각 포함되는 것을 모두 의미하는 것이다.In the present specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more C-layers and one or more D-layers, respectively.
본 명세서에 있어서, "또는"은 포괄적인 '또는'을 말하며 배타적인 '또는'을 말하는 것은 아니다. 예컨대, 조건 A 또는 B는 하기 중 어느 하나에 의해 만족된다: A는 참(또는 존재함)이고 B는 거짓(또는 존재하지 않음), A는 거짓(또는 존재하지 않음)이고 B는 참(또는 존재함), A 및 B 모두가 참(또는 존재함).In this specification, "or" refers to an inclusive 'or' and does not mean an exclusive 'or'. For example, condition A or B is satisfied by either: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or exists), and both A and B are true (or present).
본 명세서에 있어서, "이들의 혼합물" 또는 "혼합"은 2종 이상의 물질이 포함되는 것을 의미한다. 상기 "혼합물" 또는 "혼합"은 균일 및/또는 비균일하게 섞인 상태, 용해된 상태, 균일 및/또는 비균일하게 분산된 상태 등을 포함할 수 있으나, 이에만 한정되는 것은 아니다.As used herein, "a mixture thereof" or "mixture" means that two or more kinds of substances are included. The "mixture" or "mixture" may include, but is not limited to, a uniformly and/or non-uniformly mixed state, a dissolved state, a uniformly and/or non-uniformly dispersed state, and the like.
본 명세서에서 달리 정의되지 않는 한, 본 명세서에서 사용되는 모든 기술적 및 과학적 용어는 본 발명이 속하는 기술 분야의 당업자에 의해 통상적으로 이해되는 바와 동일한 의미를 갖는다. 본 명세서에서 설명되는 것과 유사하거나 등가인 방법 및 재료가 본 발명의 실시 형태의 실시 또는 시험에서 사용될 수 있지만, 적합한 방법 및 재료가 후술된다. 본 명세서에서 언급되는 모든 간행물, 특허 출원, 특허 및 다른 참고 문헌은 전체적으로 본 명세서에 참고로 포함되며, 상충되는 경우 특정 어구(passage)가 언급되지 않으면, 정의를 비롯한 본 명세서가 우선할 것이다. 게다가, 재료, 방법, 및 실시예는 단지 예시적인 것이며 제한하고자 하는 것은 아니다.Unless defined otherwise herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this specification are incorporated herein by reference in their entirety, and in the event of a conflict the present specification, including definitions, will control unless a specific passage is recited. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of substituents in the present specification are described below, but are not limited thereto.
본 명세서에 있어서,
Figure PCTKR2021095005-appb-img-000008
는 연결되는 부위를 의미한다.In this specification,
Figure PCTKR2021095005-appb-img-000008
means the part to be connected.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 같거나 상이할 수 있다.The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more substituted , two or more substituents may be the same as or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 알킬기; 시클로알킬기; 알콕시기; 알케닐기; 할로알킬기; 실릴기; 붕소기; 아민기; 아릴기; 및 헤테로아릴기로 이루어진 군으로부터 선택되는 1 이상의 치환기로 치환되었거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; hydroxyl group; cyano group; nitro group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.
본 명세서에 있어서, 2 이상의 치환기가 연결된다는 것은 어느 하나의 치환기의 수소가 다른 치환기와 연결된 것을 말한다. 예컨대, 2개의 치환기가 연결되는 것은 페닐기와 나프틸기가 연결되어
Figure PCTKR2021095005-appb-img-000009
또는
Figure PCTKR2021095005-appb-img-000010
의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어,
Figure PCTKR2021095005-appb-img-000011
,
Figure PCTKR2021095005-appb-img-000012
또는
Figure PCTKR2021095005-appb-img-000013
의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, that two or more substituents are connected means that hydrogen of any one substituent is connected with another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.
Figure PCTKR2021095005-appb-img-000009
or
Figure PCTKR2021095005-appb-img-000010
may be a substituent of In addition, the connection of three substituents means that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, as well as (substituent 2) and (substituent 3) are connected to (substituent 1). include For example, a phenyl group, a naphthyl group and an isopropyl group are connected,
Figure PCTKR2021095005-appb-img-000011
,
Figure PCTKR2021095005-appb-img-000012
or
Figure PCTKR2021095005-appb-img-000013
may be a substituent of The above definition applies equally to the case where 4 or more substituents are connected.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸, 아다만틸기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. , but is not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 할로알킬기는 상기 알킬기의 정의 중 알킬기의 수소 대신 적어도 하나의 할로겐기가 치환되는 것을 의미한다.In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라센기, 페난트렌기, 트리페닐렌기, 파이렌기, 페날렌기, 페릴렌기, 크라이센기, 플루오렌기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오렌기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
상기 플루오렌기가 치환되는 경우,
Figure PCTKR2021095005-appb-img-000014
등이 있으나, 이에 한정되지 않는다.When the fluorene group is substituted,
Figure PCTKR2021095005-appb-img-000014
and the like, but is not limited thereto.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.
본 명세서에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로아릴기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미딘기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도 피리미딘기, 피리도 피라진기, 피라지노 피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난트리딘기(phenanthridine), 페난쓰롤린기(phenanthroline), 이소옥사졸기, 티아디아졸기, 디벤조퓨란기, 디벤조실롤기, 페노크산틴기(phenoxathiine), 페녹사진기(phenoxazine), 페노티아진기(phenothiazine), 디하이드로인데노카바졸기, 스피로플루오렌잔텐기 및 스피로플루오렌티옥산텐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene There is a thioxanthene group, but is not limited thereto.
본 명세서 있어서, 상기 실릴기는 알킬실릴기, 아릴실릴기, 헤테로아릴실릴기 등일 수 있다. 상기 알킬실릴기 중 알킬기는 전술한 알킬기의 예시가 적용될 수 있고, 상기 아릴실릴기 중 아릴기는 전술한 아릴기의 예시가 적용될 수 있으며, 상기 헤테로아릴실릴기 중 헤테로아릴기는 상기 헤테로아릴기의 예시가 적용될 수 있다.In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, the examples of the above-described aryl group may be applied to the aryl group of the arylsilyl group, and the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.
본 명세서에 있어서, 붕소기는 -BR 100R 101일 수 있으며, 상기 R 100 및 R 101은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 니트릴기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Specifically, the boron group includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
본 명세서에 있어서, 아민기는 -NH 2, 알킬아민기, N-알킬아릴아민기, 아릴아민기, N-아릴헤테로아릴아민기, N-알킬헤테로아릴아민기, 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre There is a nylfluorenylamine group, an N-biphenylfluorenylamine group, and the like, but is not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다. 상기 N-알킬아릴아민기 중의 알킬기와 아릴기는 전술한 알킬기 및 아릴기의 예시와 같다.In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the above-described alkyl group and aryl group.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-아릴헤테로아릴아민기 중의 아릴기와 헤테로아릴기는 전술한 아릴기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heteroaryl group.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-알킬헤테로아릴아민기 중의 알킬기와 헤테로아릴기는 전술한 알킬기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-described alkyl group and heteroaryl group.
본 명세서에 있어서, 알킬아민기의 예로는 치환 또는 비치환된 모노알킬아민기, 또는 치환 또는 비치환된 디알킬아민기가 있다. 상기 알킬아민기 중의 알킬기는 직쇄 또는 분지쇄의 알킬기일 수 있다. 상기 알킬기를 2 이상 포함하는 알킬아민기는 직쇄의 알킬기, 분지쇄의 알킬기, 또는 직쇄의 알킬기와 분지쇄의 알킬기를 동시에 포함할 수 있다. 예컨대, 상기 알킬아민기 중의 알킬기는 전술한 알킬기의 예시 중에서 선택될 수 있다.In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched alkyl group. The alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 또는 치환 또는 비치환된 디아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. 예컨대, 상기 아릴아민기 중의 아릴기는 전술한 아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 또는 치환 또는 비치환된 디헤테로아릴아민기가 있다. 상기 헤테로아릴기가 2 이상을 포함하는 헤테로아릴아민기는 단환식 헤테로아릴기, 다환식 헤테로아릴기, 또는 단환식 헤테로아릴기와 다환식 헤테로아릴기를 동시에 포함할 수 있다. 예컨대, 상기 헤테로아릴아민기 중의 헤테로아릴기는 전술한 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
본 명세서에 있어서, 치환기 중 "인접한 2개는 서로 결합하여 고리를 형성한다"는 의미는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성하는 것을 의미한다.In the present specification, the meaning of "adjacent two of the substituents combine with each other to form a ring" means a substituted or unsubstituted hydrocarbon ring by bonding with adjacent groups; Or it means to form a substituted or unsubstituted heterocyclic ring.
본 명세서에 있어서, 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.
본 명세서에 있어서, 탄화수소고리는 방향족 탄화수소 고리, 지방족 탄화수소고리, 또는 방향족 탄화수소와 지방족 탄화수소의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or the aryl group, except for those not monovalent.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 방향족 헤테로고리는 1가가 아닌 것을 제외하고 상기 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from among the examples of the heteroaryl group except that it is not monovalent.
본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것, 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
본 명세서에 있어서, 헤테로아릴렌기는 헤테로아릴기에 결합 위치가 두 개 있는 것, 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 헤테로아릴기의 설명이 적용될 수 있다.In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.
본 명세서의 일 실시상태에 따른 유기 발광 소자는 애노드; 캐소드; 상기 애노드와 상기 캐소드 사이에 구비된 발광층; 및 상기 발광층과 상기 애노드 사이에 구비된 2층 이상의 유기물층을 포함하는 정공수송영역을 포함하는 유기 발광 소자로서, 상기 유기물층 중 발광층에 접하는 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고, 상기 발광층은 하기 화학식 2로 표시되는 화합물을 포함한다. 이때, 상기 화학식 2의 화합물의 중수소 치환율은 40 % 내지 100%이다.An organic light emitting device according to an exemplary embodiment of the present specification includes an anode; cathode; a light emitting layer provided between the anode and the cathode; and a hole transport region including two or more organic material layers provided between the light emitting layer and the anode, wherein the organic material layer in contact with the light emitting layer among the organic material layers contains a compound represented by the following formula (1), and the light emitting layer comprises: It includes a compound represented by the following formula (2). In this case, the deuterium substitution rate of the compound of Formula 2 is 40% to 100%.
상기 실시상태에 따른 유기 발광 소자는 애노드와 발광층 사이, 즉 정공 수송 영역에 화학식 1의 화합물을 포함하고, 발광층에 화학식 2의 화합물을 포함하는 것을 특징으로 한다. 유기 발광 소자의 정공 수송 영역에 화학식 1의 화합물을 포함함으로써, 정공의 주입 및 수송을 빠르게하고 발광층 내부로의 캐리어 수송을 극대화하여 발광층의 효율을 높일 수 있으며, 발광층에 화학식 2의 화합물을 포함함으로써, 우수한 수명을 갖는 소자를 얻을 수 있다.The organic light-emitting device according to the embodiment includes the compound of Formula 1 between the anode and the emission layer, that is, in the hole transport region, and the compound of Formula 2 is included in the emission layer. By including the compound of Formula 1 in the hole transport region of the organic light emitting device, injection and transport of holes can be accelerated and carrier transport into the light emitting layer can be maximized to increase the efficiency of the light emitting layer, and by including the compound of Formula 2 in the light emitting layer , it is possible to obtain a device having an excellent lifespan.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 40 % 내지 100%이고, 바람직하게는 40% 내지 99%이다. According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 40% to 100%, preferably 40% to 99%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 45 % 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 45% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 50% 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 50% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 65 % 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 65% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 70 % 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 70% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 80 % 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 80% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 90 % 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 90% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2의 중수소 치환율은 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 100%.
상기 중수소 치환율을 전술한 방법으로 계산될 수 있다. 추가의 일 예에 따르면, 상기 화학식 2의 안트라센에 직접 적어도 하나의 중수소가 치환된다. 유기 발광 소자의 발광층은 발광을 하는 영역으로서 에너지에 의한 분자의 손실이 큰 구간이다. 탄소-중수소의 결합은 탄소-수소의 결합보다 강하고, 중수소는 수소보다 높은 질량값을 가짐으로서 탄소와의 영점에너지(Zero point energy)를 낮추어 결합의 에너지가 높으므로, 상기 화학식 2의 화합물의 분자 내에 포함된 탄소-수소 결합을 탄소-중수소 결합으로 대체하여 분자의 결합에너지를 높여 우수한 수명을 갖는 소자를 얻을 수 있다.The deuterium substitution rate may be calculated by the method described above. According to a further example, at least one deuterium is directly substituted for the anthracene of Formula 2 above. The light emitting layer of the organic light emitting device is a region that emits light and has a large loss of molecules due to energy. Since the carbon-deuterium bond is stronger than the carbon-hydrogen bond, and deuterium has a higher mass value than hydrogen, the zero point energy with carbon is lowered and the energy of the bond is high, so the molecule of the compound of Formula 2 By replacing the carbon-hydrogen bond contained in the carbon-deuterium bond with the carbon-deuterium bond, it is possible to obtain a device having an excellent lifespan by increasing the molecular binding energy.
영점에너지 =
Figure PCTKR2021095005-appb-img-000015
zero point energy =
Figure PCTKR2021095005-appb-img-000015
본 명세서의 일 실시상태에 따른 중수소 치환율을 가지는 화학식 2의 화합물을 포함하는 유기 발광 소자는 소자는 수명이 개선되는 효과가 있다.The organic light emitting device including the compound of Formula 2 having a deuterium substitution rate according to an exemplary embodiment of the present specification has an effect of improving the device lifespan.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 중수소 치환율은 0% 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 1 is 0% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 중수소 치환율은 0.01% 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 1 is 0.01% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 중수소 치환율은 1% 내지 100%이다.According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 1 is 1% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 치환 가능한 위치의 수소 중 적어도 하나는 중수소로 치환된다.According to an exemplary embodiment of the present specification, at least one of the hydrogens in the substitutable positions of Formula 1 is substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 어느 하나는 상기 화학식 a로 표시되는 기이고, 상기 R8 및 R9 중 상기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 탄소수 6 내지 20의 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, any one of R8 and R9 is a group represented by Formula (a), and among R8 and R9, a group other than the group represented by Formula (a), R1 to R7 and R10 to R18 are each other same or different, each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are mutually exclusive Combined to form a polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 치환 또는 비치환된 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring to form
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other and have 6 to 20 substituted or unsubstituted carbon atoms to form an aromatic hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 치환 또는 비치환된 벤젠고리를 형성한다.According to an exemplary embodiment of the present specification, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted benzene ring do.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 벤젠고리를 형성한다.According to an exemplary embodiment of the present specification, a group other than the group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R18은 서로 결합하여, 치환 또는 비치환된 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R18 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R18은 서로 결합하여, 치환 또는 비치환된 탄소수 13 내지 20의 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R18 are bonded to each other to form a substituted or unsubstituted polycyclic aromatic hydrocarbon ring having 13 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R18은 서로 결합하여, 치환 또는 비치환된 플루오렌고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R18 are bonded to each other to form a substituted or unsubstituted fluorene ring.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R18은 서로 결합하여, 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R18 are bonded to each other to form an aromatic hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R18은 서로 결합하여, 탄소수 13 내지 20의 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R18 are bonded to each other to form a polycyclic aromatic hydrocarbon ring having 13 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1 및 R18은 서로 결합하여, 플루오렌고리를 형성한다.According to an exemplary embodiment of the present specification, R1 and R18 are bonded to each other to form a fluorene ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1 내지 1-4 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
[화학식 1-1][Formula 1-1]
Figure PCTKR2021095005-appb-img-000016
Figure PCTKR2021095005-appb-img-000016
[화학식 1-2][Formula 1-2]
Figure PCTKR2021095005-appb-img-000017
Figure PCTKR2021095005-appb-img-000017
[화학식 1-3][Formula 1-3]
Figure PCTKR2021095005-appb-img-000018
Figure PCTKR2021095005-appb-img-000018
[화학식 1-4][Formula 1-4]
Figure PCTKR2021095005-appb-img-000019
Figure PCTKR2021095005-appb-img-000019
상기 화학식 1-1 내지 1-4에 있어서,In Formulas 1-1 to 1-4,
R2 내지 R17, R101 및 R118은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R2 to R17, R101 and R118 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 내지 L3, l1 내지 l3, Ar1 및 Ar2의 정의는 상기 화학식 a에서 정의한 바와 동일하다.The definitions of L1 to L3, 11 to 13, Ar1 and Ar2 are the same as those defined in Formula (a) above.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 10의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C10 linear or branched alkyl group; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 알킬기; 또는 중수소로 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; an alkyl group; Or an aryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 10의 직쇄 또는 분지쇄의 알킬기; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 10의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 10 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms that is unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; tert-부틸기; 또는 중수소로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; tert-butyl group; Or a phenyl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7, R11 및 R13 내지 R18은 수소이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7, R11 and R13 to R18 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R12는 수소; tert-부틸기; 또는 페닐기이다.According to an exemplary embodiment of the present specification, R12 is hydrogen; tert-butyl group; or a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6 및 R12 내지 R18은 수소이다.According to an exemplary embodiment of the present specification, among R8 and R9, a group other than a group represented by the following formula (a), R1 to R6 and R12 to R18 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R7은 중수소로 치환된 페닐기이다.According to an exemplary embodiment of the present specification, R7 is a phenyl group substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 l1은 1이다.According to an exemplary embodiment of the present specification, l1 is 1.
본 명세서의 일 실시상태에 따르면, 상기 l1은 2이다.According to an exemplary embodiment of the present specification, l1 is 2.
본 명세서의 일 실시상태에 따르면, 상기 l2는 1이다.According to an exemplary embodiment of the present specification, l2 is 1.
본 명세서의 일 실시상태에 따르면, 상기 l3은 1이다.According to an exemplary embodiment of the present specification, l3 is 1.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소, 알킬기, 및 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 아릴렌기; 또는 중수소, 또는 알킬기로 치환 또는 비치환된 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; an arylene group unsubstituted or substituted with one or more selected from deuterium, an alkyl group, and an aryl group; or a heteroarylene group unsubstituted or substituted with deuterium or an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 중수소, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms which is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 20의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 중수소, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium or a linear or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 터페닐릴렌기; 중수소, 탄소수 1 내지 20의 알킬기, 및 탄소수 6 내지 20의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환된 2가의 플루오렌기; 또는 중수소로 치환 또는 비치환된 2가의 벤조퓨란기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; a divalent fluorene group substituted with one or more selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a divalent benzofuran group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 터페닐릴렌기; 중수소, 메틸기, 및 페닐기 중에서 선택되는 1 이상으로 치환된 2가의 플루오렌기; 또는 중수소로 치환 또는 비치환된 2가의 벤조퓨란기 이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; a divalent fluorene group substituted with one or more selected from deuterium, a methyl group, and a phenyl group; or a divalent benzofuran group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 바이페닐릴렌기; 터페닐릴렌기; 메틸기, 및 페닐기 중에서 선택되는 1 이상으로 치환된 2가의 플루오렌기; 또는 2가의 벤조퓨란기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; biphenylrylene group; terphenylrylene group; a divalent fluorene group substituted with one or more selected from a methyl group and a phenyl group; or a divalent benzofuran group.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 치환 또는 비치환된 탄소수 6 내지 15의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 15의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 중수소로 치환 또는 비치환된 아릴렌기; 또는 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; an arylene group unsubstituted or substituted with deuterium; or a heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 중수소로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 중수소로 치환 또는 비치환된 탄소수 6 내지 15의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 15의 단환 또는 다환의 헤테로아릴렌기이다According to an exemplary embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 또는 2가의 벤조퓨란기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; or a divalent benzofuran group.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 바이페닐릴렌기; 또는 2가의 벤조퓨란기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; biphenylrylene group; or a divalent benzofuran group.
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 중수소, 알킬기, 및 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or an arylene group unsubstituted or substituted with one or more selected from deuterium, an alkyl group, and an aryl group.
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 중수소, 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 20의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 터페닐릴렌기; 또는 중수소, 탄소수 1 내지 20의 알킬기, 및 탄소수 6 내지 20의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환된 2가의 플루오렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; or a divalent fluorene group substituted with one or more selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 터페닐릴렌기; 또는 중수소, 메틸기, 및 페닐기 중에서 선택되는 1 이상으로 치환된 2가의 플루오렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; terphenylrylene group unsubstituted or substituted with deuterium; or a divalent fluorene group substituted with one or more selected from deuterium, a methyl group, and a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L2 및 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 바이페닐릴렌기; 터페닐릴렌기; 또는 메틸기, 및 페닐기 중에서 선택되는 1 이상으로 치환된 2가의 플루오렌기이다.According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; biphenylrylene group; terphenylrylene group; or a divalent fluorene group substituted with one or more selected from a methyl group and a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 중수소로 치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1이상으로 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a straight or branched chain having 1 to 30 carbon atoms substituted with deuterium A monocyclic or polycyclic aryl having 6 to 30 carbon atoms unsubstituted or substituted with one or more selected from an alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. energy; Or at least one selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 중수소로 치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 페닐기; 중수소, 및 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기 중에서 선택되는 1 이상으로 치환 또는 비치환된 바이페닐기; 터페닐기; 쿼터페닐기; 중수소로 치환 또는 비치환된 나프틸기; 중수소로 치환 또는 비치환된 페난트렌기; 트리페닐렌기; 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 중수소로 치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1이상으로 치환된 플루오렌기; 카바졸기; 디벤조퓨란기; 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a straight or branched chain having 1 to 30 carbon atoms substituted with deuterium a phenyl group unsubstituted or substituted with one or more selected from an alkyl group and a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a biphenyl group unsubstituted or substituted with one or more selected from deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms; terphenyl group; quarter phenyl group; a naphthyl group unsubstituted or substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; triphenylene group; Deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with one or more selected from fluorene group; a carbazole group; dibenzofuran group; a benzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 중수소, tert-부틸기, 트리메틸실릴기, 메틸기 및 페닐기 중에서 선택되는 1 이상으로 치환 또는 비치환된 페닐기; 중수소, 및 tert-부틸기 중에서 선택되는 1 이상으로 치환 또는 비치환된 바이페닐기; 터페닐기; 쿼터페닐기; 중수소로 치환 또는 비치환된 나프틸기; 중수소로 치환 또는 비치환된 페난트렌기; 트리페닐렌기; 중수소, 트리튜테리움메틸기, 메틸기, 및 페닐기 중에서 선택되는 1이상으로 치환된 플루오렌기; 카바졸기; 디벤조퓨란기; 페닐기로 치환 또는 비치환된 벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more selected from deuterium, tert-butyl group, trimethylsilyl group, methyl group and phenyl group; a biphenyl group unsubstituted or substituted with one or more selected from deuterium, and a tert-butyl group; terphenyl group; quarter phenyl group; a naphthyl group unsubstituted or substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; triphenylene group; a fluorene group substituted with one or more selected from deuterium, a trituterium methyl group, a methyl group, and a phenyl group; a carbazole group; dibenzofuran group; a benzofuran group unsubstituted or substituted with a phenyl group; or a dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 R101 및 R118은 수소이다.According to an exemplary embodiment of the present specification, R101 and R118 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more selected from a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 페닐기; 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 나프틸기; 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택된 1 이상으로 치환 또는 비치환된 바이페닐기; 중수소로 치환된 터페닐기; 중수소로 치환 또는 비치환된 페난트렌기; 중수소로 치환 또는 비치환된 트리페닐렌기; 또는 중수소로 치환 또는 비치환된 파이렌기이다.According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with one or more selected from monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium; a naphthyl group unsubstituted or substituted with one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; a biphenyl group unsubstituted or substituted with one or more selected from monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium; a terphenyl group substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; a triphenylene group unsubstituted or substituted with deuterium; Or a pyrene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소, 중수소로 치환 또는 비치환된 페닐기, 중수소로 치환 또는 비치환된 바이페닐기, 및 중수소로 치환 또는 비치환된 나프틸기 중에서 선택되는 1 이상으로 치환 또는 비치환된 페닐기; 중수소, 중수소, 중수소로 치환 또는 비치환된 페닐기, 중수소로 치환 또는 비치환된 바이페닐기, 및 중수소로 치환 또는 비치환된 나프틸기 중에서 선택되는 1 이상으로 치환 또는 비치환된 나프틸기; 중수소, 및 중수소로 치환 또는 비치환된 페닐기 중에서 선택된 1 이상으로 치환 또는 비치환된 바이페닐기; 중수소로 치환된 터페닐기; 중수소로 치환 또는 비치환된 페난트렌기; 중수소로 치환 또는 비치환된 트리페닐렌기; 또는 중수소로 치환 또는 비치환된 파이렌기이다.According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following Chemical Formula b, the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group substituted or unsubstituted with one or more selected from a phenyl group substituted or unsubstituted with deuterium, a phenyl group unsubstituted or substituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with one or more selected from deuterium, deuterium, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with deuterium; a biphenyl group unsubstituted or substituted with one or more selected from deuterium and a phenyl group unsubstituted or substituted with deuterium; a terphenyl group substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; a triphenylene group unsubstituted or substituted with deuterium; Or a pyrene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 G1은 상기 화학식 b로 표시되는 기이다.According to an exemplary embodiment of the present specification, G1 is a group represented by Formula b.
본 명세서의 일 실시상태에 따르면, 상기 G3은 상기 화학식 b로 표시되는 기이다.According to an exemplary embodiment of the present specification, G3 is a group represented by Formula b.
본 명세서의 일 실시상태에 따르면, 상기 G1 및 G6은 서로 같거나 상이하고, 각각 상기 화학식 b로 표시되는 기이다.According to an exemplary embodiment of the present specification, G1 and G6 are the same as or different from each other, and are each a group represented by Formula b.
본 명세서의 일 실시상태에 따르면, 상기 l4는 1이다.According to an exemplary embodiment of the present specification, 14 is 1.
본 명세서의 일 실시상태에 따르면, 상기 L4는 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L4 is a direct bond; or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L4는 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L4 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L4는 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L4 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L4는 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L4 is a direct bond; or a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L4는 직접결합; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L4 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L4는 직접결합; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L4 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 L4는 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 또는 중수소로 치환 또는 비치환된 나프틸렌기이다.According to an exemplary embodiment of the present specification, L4 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 A 및 B는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 방향족 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리이다.According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring.
본 명세서의 일 실시상태에 따르면, 상기 A 및 B는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리이다.According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 A 및 B는 서로 같거나 상이하고, 각각 독립적으로 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리이다.According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and each independently at least one selected from a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium. a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 A 및 B는 서로 같거나 상이하고, 각각 독립적으로 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 벤젠고리; 중수소로 치환 또는 비치환된 나프탈렌고리; 중수소로 치환 또는 비치환된 페난트렌고리; 중수소로 치환 또는 비치환된 트리페닐렌고리; 또는 중수소로 치환 또는 비치환된 디벤조퓨란고리이다.According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and each independently at least one selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium. a substituted or unsubstituted benzene ring; a naphthalene ring unsubstituted or substituted with deuterium; a phenanthrene ring unsubstituted or substituted with deuterium; a triphenylene ring unsubstituted or substituted with deuterium; Or a dibenzofuran ring unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 A 및 B는 서로 같거나 상이하고, 각각 독립적으로 중수소, 중수소로 치환 또는 비치환된 페닐기, 중수소로 치환 또는 비치환된 바이페닐기, 및 중수소로 치환 또는 비치환된 나프닐기 중에서 선택되는 1 이상으로 치환 또는 비치환된 벤젠고리; 중수소로 치환 또는 비치환된 나프탈렌고리; 중수소로 치환 또는 비치환된 페난트렌고리; 중수소로 치환 또는 비치환된 트리페닐렌고리; 또는 중수소로 치환 또는 비치환된 디벤조퓨란고리이다.According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and each independently deuterium, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and deuterium substituted or unsubstituted a benzene ring unsubstituted or substituted with one or more selected from cyclic naphnyl groups; a naphthalene ring unsubstituted or substituted with deuterium; a phenanthrene ring unsubstituted or substituted with deuterium; a triphenylene ring unsubstituted or substituted with deuterium; Or a dibenzofuran ring unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds.
Figure PCTKR2021095005-appb-img-000020
Figure PCTKR2021095005-appb-img-000020
Figure PCTKR2021095005-appb-img-000021
Figure PCTKR2021095005-appb-img-000021
Figure PCTKR2021095005-appb-img-000022
Figure PCTKR2021095005-appb-img-000022
Figure PCTKR2021095005-appb-img-000023
Figure PCTKR2021095005-appb-img-000023
Figure PCTKR2021095005-appb-img-000024
Figure PCTKR2021095005-appb-img-000024
Figure PCTKR2021095005-appb-img-000025
Figure PCTKR2021095005-appb-img-000025
Figure PCTKR2021095005-appb-img-000026
Figure PCTKR2021095005-appb-img-000026
Figure PCTKR2021095005-appb-img-000027
Figure PCTKR2021095005-appb-img-000027
Figure PCTKR2021095005-appb-img-000028
Figure PCTKR2021095005-appb-img-000028
Figure PCTKR2021095005-appb-img-000029
Figure PCTKR2021095005-appb-img-000029
Figure PCTKR2021095005-appb-img-000030
Figure PCTKR2021095005-appb-img-000030
Figure PCTKR2021095005-appb-img-000031
Figure PCTKR2021095005-appb-img-000031
Figure PCTKR2021095005-appb-img-000032
Figure PCTKR2021095005-appb-img-000032
Figure PCTKR2021095005-appb-img-000033
Figure PCTKR2021095005-appb-img-000033
Figure PCTKR2021095005-appb-img-000034
Figure PCTKR2021095005-appb-img-000034
Figure PCTKR2021095005-appb-img-000035
Figure PCTKR2021095005-appb-img-000035
Figure PCTKR2021095005-appb-img-000036
Figure PCTKR2021095005-appb-img-000036
Figure PCTKR2021095005-appb-img-000037
Figure PCTKR2021095005-appb-img-000037
Figure PCTKR2021095005-appb-img-000038
Figure PCTKR2021095005-appb-img-000038
Figure PCTKR2021095005-appb-img-000039
Figure PCTKR2021095005-appb-img-000039
Figure PCTKR2021095005-appb-img-000040
Figure PCTKR2021095005-appb-img-000040
Figure PCTKR2021095005-appb-img-000041
Figure PCTKR2021095005-appb-img-000041
Figure PCTKR2021095005-appb-img-000042
Figure PCTKR2021095005-appb-img-000042
Figure PCTKR2021095005-appb-img-000043
Figure PCTKR2021095005-appb-img-000043
Figure PCTKR2021095005-appb-img-000044
Figure PCTKR2021095005-appb-img-000044
Figure PCTKR2021095005-appb-img-000045
Figure PCTKR2021095005-appb-img-000045
Figure PCTKR2021095005-appb-img-000046
Figure PCTKR2021095005-appb-img-000046
Figure PCTKR2021095005-appb-img-000047
Figure PCTKR2021095005-appb-img-000047
Figure PCTKR2021095005-appb-img-000048
Figure PCTKR2021095005-appb-img-000048
Figure PCTKR2021095005-appb-img-000049
Figure PCTKR2021095005-appb-img-000049
Figure PCTKR2021095005-appb-img-000050
Figure PCTKR2021095005-appb-img-000050
Figure PCTKR2021095005-appb-img-000051
Figure PCTKR2021095005-appb-img-000051
Figure PCTKR2021095005-appb-img-000052
.
Figure PCTKR2021095005-appb-img-000052
.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2는 하기 화합물 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 2 is any one selected from the following compounds.
Figure PCTKR2021095005-appb-img-000053
Figure PCTKR2021095005-appb-img-000053
Figure PCTKR2021095005-appb-img-000054
Figure PCTKR2021095005-appb-img-000054
Figure PCTKR2021095005-appb-img-000055
Figure PCTKR2021095005-appb-img-000055
Figure PCTKR2021095005-appb-img-000056
Figure PCTKR2021095005-appb-img-000056
Figure PCTKR2021095005-appb-img-000057
Figure PCTKR2021095005-appb-img-000057
Figure PCTKR2021095005-appb-img-000058
Figure PCTKR2021095005-appb-img-000058
Figure PCTKR2021095005-appb-img-000059
Figure PCTKR2021095005-appb-img-000059
Figure PCTKR2021095005-appb-img-000060
Figure PCTKR2021095005-appb-img-000060
Figure PCTKR2021095005-appb-img-000061
Figure PCTKR2021095005-appb-img-000061
Figure PCTKR2021095005-appb-img-000062
Figure PCTKR2021095005-appb-img-000062
Figure PCTKR2021095005-appb-img-000063
Figure PCTKR2021095005-appb-img-000063
Figure PCTKR2021095005-appb-img-000064
Figure PCTKR2021095005-appb-img-000064
Figure PCTKR2021095005-appb-img-000065
Figure PCTKR2021095005-appb-img-000065
Figure PCTKR2021095005-appb-img-000066
Figure PCTKR2021095005-appb-img-000066
Figure PCTKR2021095005-appb-img-000067
Figure PCTKR2021095005-appb-img-000067
Figure PCTKR2021095005-appb-img-000068
Figure PCTKR2021095005-appb-img-000068
Figure PCTKR2021095005-appb-img-000069
Figure PCTKR2021095005-appb-img-000069
Figure PCTKR2021095005-appb-img-000070
Figure PCTKR2021095005-appb-img-000070
Figure PCTKR2021095005-appb-img-000071
Figure PCTKR2021095005-appb-img-000071
Figure PCTKR2021095005-appb-img-000072
Figure PCTKR2021095005-appb-img-000072
Figure PCTKR2021095005-appb-img-000073
Figure PCTKR2021095005-appb-img-000073
Figure PCTKR2021095005-appb-img-000074
Figure PCTKR2021095005-appb-img-000074
Figure PCTKR2021095005-appb-img-000075
Figure PCTKR2021095005-appb-img-000075
Figure PCTKR2021095005-appb-img-000076
Figure PCTKR2021095005-appb-img-000076
Figure PCTKR2021095005-appb-img-000077
Figure PCTKR2021095005-appb-img-000077
Figure PCTKR2021095005-appb-img-000078
Figure PCTKR2021095005-appb-img-000078
Figure PCTKR2021095005-appb-img-000079
Figure PCTKR2021095005-appb-img-000079
Figure PCTKR2021095005-appb-img-000080
Figure PCTKR2021095005-appb-img-000080
Figure PCTKR2021095005-appb-img-000081
Figure PCTKR2021095005-appb-img-000081
Figure PCTKR2021095005-appb-img-000082
Figure PCTKR2021095005-appb-img-000082
Figure PCTKR2021095005-appb-img-000083
Figure PCTKR2021095005-appb-img-000083
Figure PCTKR2021095005-appb-img-000084
.
Figure PCTKR2021095005-appb-img-000084
.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1 및 2의 화합물은 당 기술분야에 알려져 있는 출발물질, 반응조건을 이용하여 제조될 수 있다. 치환기의 종류 및 개수는 당업자가 공지된 출발물질을 적절히 선택함에 따라 결정할 수 있다. 또한, 상기 화학식 1 및 2의 화합물은 시판되는 것으로부터 입수될 수 있다.According to an exemplary embodiment of the present specification, the compounds of Formulas 1 and 2 may be prepared using starting materials and reaction conditions known in the art. The type and number of substituents can be determined by those skilled in the art by appropriately selecting known starting materials. In addition, the compounds of Formulas 1 and 2 may be obtained from commercially available ones.
본 명세서의 일 실시상태에 따르면, 상기 유기물층 중 애노드에 접하는 유기물층은 카바졸계 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer in contact with the anode among the organic material layer includes a carbazole-based compound.
본 명세서의 일 실시상태에 따르면, 상기 카바졸계 화합물은 하기 구조식으로 표시될 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the carbazole-based compound may be represented by the following structural formula, but is not limited thereto.
Figure PCTKR2021095005-appb-img-000085
Figure PCTKR2021095005-appb-img-000085
상기 구조식에 있어서,In the structural formula,
T1 내지 T3는 서로 같거나 상이하고, 각각 독립적으로 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 알킬기; 시클로알킬기; 알콕시기; 알케닐기; 할로알킬기; 실릴기; 붕소기; 아민기; 아릴기; 또는 헤테로아릴기이거나, 인접합 기는 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,T1 to T3 are the same as or different from each other, and each independently deuterium; halogen group; hydroxyl group; cyano group; nitro group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; or a heteroaryl group, or adjacent groups may combine with each other to form a substituted or unsubstituted ring,
t1은 1 내지 4의 정수이며, 상기 t1이 2 이상인 경우, 2 이상의 상기 T1은 서로 같거나 상이하며,t1 is an integer of 1 to 4, and when t1 is 2 or more, T1 of 2 or more are the same as or different from each other,
t2는 1 내지 4의 정수이고, 상기 t2가 2 이상인 경우, 2 이상의 상기 T2는 서로 같거나 상이하고, t2 is an integer of 1 to 4, and when t2 is 2 or more, T2 or more are the same as or different from each other,
t3는 1 내지 10의 정수이며, 상기 t3가 2 이상인 경우, 2 이상의 상기 T3는 서로 같거나 상이하다.t3 is an integer of 1 to 10, and when t3 is 2 or more, T3 of 2 or more are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 카바졸계 화합물은 하기 화합물 중에서 선택될 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the carbazole-based compound may be selected from the following compounds, but is not limited thereto.
Figure PCTKR2021095005-appb-img-000086
Figure PCTKR2021095005-appb-img-000086
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공수송층 및 정공조절층을 포함하고, 상기 정공수송층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole transport layer and a hole control layer, and the hole transport layer includes a compound represented by Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공수송층 및 정공조절층을 포함하고, 상기 정공조절층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole transport layer and a hole control layer, and the hole control layer includes a compound represented by Formula 1 above.
본 명세서의 일 실시상태에 따른 정공조절층은 상기 화학식 1로 표시되는 화합물을 포함하고, 상기 화학식 1의 중수소 치환율은 1% 내지 100%이다.The hole control layer according to an exemplary embodiment of the present specification includes the compound represented by Formula 1, and the deuterium substitution rate of Formula 1 is 1% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 애노드와 상기 발광층 사이에 상기 정공수송층 및 정공조절층을 포함하는 정공수송영역을 포함하며, 상기 정공수송층과 상기 정공조절층은 접하여 구비된다.According to an exemplary embodiment of the present specification, a hole transport region including the hole transport layer and the hole control layer is included between the anode and the light emitting layer, and the hole transport layer and the hole control layer are provided in contact with each other.
본 명세서의 일 실시상태에 따르면, 상기 정공조절층은 상기 발광층에 접하여 구비된다.According to an exemplary embodiment of the present specification, the hole control layer is provided in contact with the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 애노드와 상기 정공수송층 사이에 정공주입층을 포함할 수 있다.According to an exemplary embodiment of the present specification, a hole injection layer may be included between the anode and the hole transport layer.
본 명세서의 유기 발광 소자의 구조는 예컨대, 도 1 내지 4에 나타난 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present specification may have, for example, the structure shown in FIGS. 1 to 4 , but is not limited thereto.
도 1에는 기판(1) 위에 애노드(2), 정공수송영역(3), 발광층(4) 및 캐소드(5)가 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 도 1은 본 명세서의 일 실시상태에 따른 예시적인 구조이며, 다른 유기물층을 더 포함할 수 있다.1 illustrates a structure of an organic light emitting device in which an anode 2, a hole transport region 3, a light emitting layer 4, and a cathode 5 are sequentially stacked on a substrate 1 . 1 is an exemplary structure according to an embodiment of the present specification, and may further include another organic material layer.
도 2에는 기판(1) 위에 애노드(2), 정공수송층(3-1) 및 정공조절층(3-2)를 포함하는 정공수송영역(3), 발광층(4) 및 캐소드(5)가 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 도 2는 본 명세서의 일 실시상태에 따른 예시적인 구조이며, 다른 유기물층을 더 포함할 수 있다. 2, the anode 2, the hole transport layer 3-1, and the hole transport region 3 including the hole control layer 3-2, the light emitting layer 4 and the cathode 5 are sequentially on the substrate 1 The structure of the organic light emitting device stacked with 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
도 3에는 기판(1) 위에 애노드(2), 정공주입층(6), 정공수송영역(3), 발광층(4), 전자수송영역(7), 전자주입층(8) 및 캐소드(5)가 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 도 3은 본 명세서의 일 실시상태에 따른 예시적인 구조이며, 다른 유기물층을 더 포함할 수 있다.3 shows an anode 2, a hole injection layer 6, a hole transport region 3, a light emitting layer 4, an electron transport region 7, an electron injection layer 8 and a cathode 5 on the substrate 1 A structure of an organic light emitting device in which is sequentially stacked is illustrated. 3 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
도 4에는 기판(1) 위에 애노드(2), 정공주입층(6), 정공수송층(3-1) 및 정공조절층(3-2)를 포함하는 정공수송영역(3), 발광층(4), 전자조절층(7-1) 및 전자수송층(7-2)를 포함하는 전자수송영역(7), 전자주입층(8) 및 캐소드(5)가 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 도 4은 본 명세서의 일 실시상태에 따른 예시적인 구조이며, 다른 유기물층을 더 포함할 수 있다.4 shows the anode 2, the hole injection layer 6, the hole transport region 3 including the hole transport layer 3-1 and the hole control layer 3-2 on the substrate 1, the light emitting layer (4) , the electron transport region 7 including the electron control layer 7-1 and the electron transport layer 7-2, the electron injection layer 8 and the cathode 5 are sequentially stacked, the structure of the organic light emitting device is exemplified has been 4 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층의 두께는 50 nm 내지 200nm 이다.According to an exemplary embodiment of the present specification, the thickness of the hole transport layer is 50 nm to 200 nm.
본 명세서의 일 실시상태에 따르면, 상기 정공조절층의 두깨는 10 nm 내지 150 nm 이다.According to an exemplary embodiment of the present specification, the thickness of the hole control layer is 10 nm to 150 nm.
상기 정공수송영역은 정공수송층과 정공조절층이 포함되는 복수 혹은 단수의 층으로 구성되어 있으며 유기 발광 소자의 광학적 특성을 최적화하기 위하여 상기 두께 내의 최적점을 기준으로 정공수송영역의 두께를 결정할 수 있다.The hole transport region is composed of a plurality or a single layer including a hole transport layer and a hole control layer, and the thickness of the hole transport region can be determined based on an optimum point within the thickness in order to optimize the optical properties of the organic light emitting device. .
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 삼중항 에너지는 2.4eV 내지 2.8eV 이다.According to an exemplary embodiment of the present specification, the triplet energy of Formula 1 is 2.4eV to 2.8eV.
본 명세서의 일 실시상태에 따른 정공 수송 영역 중 발광층에 접해있는 층 즉, 상기 화학식 1을 포함하는 층이 상기 삼중항 에너지 범위를 갖는 경우, 상대적으로 높은 일중항 에너지를 나타내는 것이 통상적이며 이에 따라 낮은 최고 점유 오비탈 에너지를 가지는 경우가 일반적이다. 따라서 발광층에서의 캐리어 및 엑시톤 이동 혹은 전이가 용이하지 않으므로 제작된 유기 발광 소자의 효율을 높이고 안정성을 이끌어 낼 수 있다.In the case of a layer in contact with the light emitting layer in the hole transport region according to an exemplary embodiment of the present specification, that is, a layer including Formula 1 has the triplet energy range, it is common to exhibit a relatively high singlet energy, and thus a low It is common to have the highest occupied orbital energy. Therefore, since carrier and exciton movement or transition in the light emitting layer is not easy, the efficiency of the fabricated organic light emitting device can be improved and stability can be derived.
본 명세서에 있어서, "에너지 준위"는 에너지 크기를 의미하는 것이다. 따라서 에너지 준위는 해당 에너지 값의 절대값을 의미하는 것으로 해석된다. 예컨대, 에너지 준위가 낮거나 깊다는 것은 진공 준위로부터 마이너스 방향으로 절대값이 커지는 것을 의미한다.As used herein, "energy level" means an energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, when the energy level is low or deep, it means that the absolute value increases in the negative direction from the vacuum level.
본 명세서에 있어서, HOMO(highest occupied molecular orbital)란, 전자가 결합에 참여할 수 있는 영역에서 가장 에너지가 높은 영역에 있는 분자궤도함수(최고 점유 분자 오비탈)를 의미하고, LUMO(lowest unoccupied molecular orbital)란, 전자가 반결합영역 중 가장 에너지가 낮은 영역에 있는 분자궤도함수(최저 비점유 분자 오비탈)를 의미하고, HOMO 에너지 준위란 진공 준위로부터 HOMO까지의 거리를 의미한다. 또한, LUMO 에너지 준위란 진공 준위로부터 LUMO까지의 거리를 의미한다. 분자 내에서 전자의 분포를 파악하고 광학적인 물성을 파악하기 위해서는 결정된 구조가 필요하다. 또한 전자구조는 분자의 전하 상태에 따라 중성, 음이온, 양이온 상태에서 각기 다른 구조를 갖는다. 소자의 구동을 위해서는 중성 상태, 양이온, 음이온 상태의 에너지 레벨이 모두 중요하나, 대표적으로 중성 상태의 HOMO (highest occupied molecular orbital)과 LUMO (lowest unoccupied molecular orbital)이 중요한 물성으로 인식된다. 화학물질의 분자구조를 결정하기 위해 범밀도 함수 방법 (density functional theory)를 사용하여 입력한 구조를 최적화한다. DFT 계산을 위해서 BPW91 계산법 (Becke exchange and Perdew correlation-correlation functional)과 DNP (double numerical basis set including polarization functional) 기저 집합(basis set)을 사용한다. BPW91 계산법은 논문 A. D. Becke, Phys. Rev. A, 38, 3098 (1988) '와 'J. P. Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992) '에 게시되어 있고, DNP 기저 집합은 논문 'B. Delley, J. Chem. Phys., 92, 508 (1990)'에 게시되어 있다. In the present specification, the highest occupied molecular orbital (HOMO) refers to a molecular orbital (highest occupied molecular orbital) in the region with the highest energy in the region where electrons can participate in bonding, and the lowest unoccupied molecular orbital (LUMO). is the molecular orbital function (lowest unoccupied molecular orbital) in which electrons are in the lowest energy region among the anti-bonding regions, and the HOMO energy level means the distance from the vacuum level to the HOMO. In addition, the LUMO energy level means the distance from the vacuum level to the LUMO. In order to understand the distribution of electrons in the molecule and to understand the optical properties, a determined structure is required. In addition, the electronic structure has different structures in neutral, anion, and cation states depending on the charge state of the molecule. Neutral state, cation, and anion energy levels are all important for driving a device, but HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) in neutral state are typically recognized as important physical properties. Optimize the input structure using density functional theory to determine the molecular structure of the chemical. For DFT calculation, BPW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and DNP (double numerical basis set including polarization functional) basis set are used. The BPW91 calculation method is described in the paper A. D. Becke, Phys. Rev. A, 38, 3098 (1988) ' and 'J. P. Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992) ', and the DNP basis set was published in the paper 'B. Delley, J. Chem. Phys., 92, 508 (1990).
범밀도 함수 방법으로 계산을 수행하기 위해 Biovia사의 'DMol3' package를 사용할 수 있다. 상기 주어진 방법을 이용해서 최적 분자구조를 결정하게 되면 전자가 점유할 수 있는 에너지 레벨을 결과로 얻을 수 있다. Biovia's 'DMol3' package can be used to perform calculations using the full-density function method. If the optimal molecular structure is determined using the method given above, the energy level that electrons can occupy can be obtained as a result.
본 명세서에 있어서, 삼중항 에너지는 분자에서 스핀양자수가 1인 전자상태를 의미한다. 상기 삼중항 에너지는 전술한 방법으로 결정된 최적 분자 구조에 대하여 들뜬 상태의 물성을 구하기 위해 시간 의존 범밀도 함수 방법 (time dependent density functional theory: TD-DFT)을 이용하여 단일항과 삼중항의 에너지 레벨을 계산한다. 범밀도 함수 계산은 가우시안 (Gaussian)사에서 개발한 상용 계산 프로그램인 'Gaussian09' package를 사용하여 수행할 수 있다. 시간 의존 범밀도 함수 계산을 위해서 B3PW91 계산법 (Becke exchange and Perdew correlation-correlation functional)과 6-31G* 기저 집합 (basis set)을 사용한다. 6-31G* 기저 집합은 논문 'J. A. Pople et al., J. Chem. Phys. 56, 2257 (1972)'에 게시되어 있다. 범밀도 함수 방법을 사용하여 결정한 최적 분자구조에 대해 전자 배열이 단일항(single) 및 삼중항 (triplet)일 때 가지는 에너지를 시간 의존 범밀도 함수 방법 (TD-DFT)을 이용하여 계산한다.In the present specification, triplet energy refers to an electronic state in which the spin quantum number is 1 in a molecule. The triplet energy is the energy level of a singlet and a triplet using a time dependent density functional theory (TD-DFT) to obtain the properties of an excited state with respect to the optimal molecular structure determined by the above method. Calculate. The general density function calculation can be performed using the 'Gaussian09' package, a commercial calculation program developed by Gaussian. The B3PW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and the 6-31G* basis set are used to calculate the time-dependent universal density function. The 6-31G* basis set is described in the paper 'J. A. Pople et al., J. Chem. Phys. 56, 2257 (1972)'. For the optimal molecular structure determined using the universal density function method, the energy when the electron arrangement is singlet and triplet is calculated using the time-dependent universal density function method (TD-DFT).
본 명세서의 일 실시상태에 따르면, 상기 발광층은 호스트 및 도펀트를 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant.
본 명세서의 일 실시상태에 따르면, 상기 호스트 및 도펀트를 포함하고, 상기 호스트는 상기 화학식 2로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the host and the dopant are included, and the host includes the compound represented by Formula 2 above.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 청색 도펀트이다.According to an exemplary embodiment of the present specification, the dopant is a blue dopant.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 청색 유기 발광 소자이다.According to an exemplary embodiment of the present specification, the organic light emitting device is a blue organic light emitting device.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 2 종 이상의 혼합 호스트를 포함하고, 상기 2 종 이상의 혼합 호스트 중 1종 이상은 상기 화학식 2로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes two or more types of mixed hosts, and at least one of the two or more types of mixed hosts includes the compound represented by Formula 2 above.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 2 종 이상의 혼합 호스트를 포함하고, 상기 2 종 이상의 혼합 호스트는 중 적어도 1종은 상기 화학식 2로 표시되는 화합물을 포함하고, 나머지는 중수소를 치환기로 포함하지 않는 안트라센계 화합물을 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes two or more kinds of mixed hosts, and at least one of the two or more kinds of mixed hosts includes a compound represented by Formula 2, and the remainder is deuterium as a substituent It contains the anthracene-type compound which does not contain it.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 2 종 이상의 혼합 호스트를 포함하고, 상기 2 종 이상의 혼합 호스트는 중 적어도 1종은 상기 화학식 2로 표시되는 화합물을 포함하고, 나머지는 중수소를 치환기로 포함하고 상기 화학식 2와 상이한 안트라센계 화합물을 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes two or more kinds of mixed hosts, and at least one of the two or more kinds of mixed hosts includes a compound represented by Formula 2, and the remainder is deuterium as a substituent and includes an anthracene-based compound different from Formula 2 above.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 2 종 이상의 혼합 호스트를 포함하고, 상기 2 종 이상의 혼합 호스트는 중 적어도 1종은 상기 화학식 2로 표시되는 화합물을 포함하고, 나머지는 중수소를 치환기로 포함하지 않는 안트라센계 화합물, 및 중수소를 치환기로 포함하고 상기 화학식 2와 상이한 안트라센계 화합물 중에서 선택되는 1 이상을 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes two or more kinds of mixed hosts, and at least one of the two or more kinds of mixed hosts includes a compound represented by Formula 2, and the remainder is deuterium as a substituent anthracene-based compounds that do not include, and at least one selected from anthracene-based compounds that contain deuterium as a substituent and are different from those of Formula 2 above.
상기 2 종 이상의 혼합 호스트는 중 적어도 1종은 상기 화학식 2로 표시되는 화합물을 포함하고, 나머지는 상기 화학식 2와 상이하다면 당 기술분야에서 사용하는 안트라센계 호스트라면 제한 없이 사용할 수 있으며, 이에만 한정되는 것은 아니다.At least one of the two or more types of mixed hosts includes a compound represented by Formula 2, and the rest may be used without limitation as long as it is an anthracene-based host used in the art if it is different from Formula 2 above, limited only to this it's not going to be
본 명세서의 일 실시상태에 따른 2종 이상의 혼합 호스트를 사용하는 유기 발광 소자는 각각 호스트의 장점을 혼합하여, 소자의 성능을 향상시키고자 함이며, 예컨대, 2종의 호스트를 혼합하는 경우, 고효율 및 저전압의 효과를 갖는 호스트 1 종과 장수명의 효과를 갖는 호스트 1종을 혼합하여, 고효율, 저전압 및 장수명의 효과를 갖는 유기 발광 소자를 제작할 수 있다.The organic light emitting device using two or more types of mixed hosts according to an exemplary embodiment of the present specification is intended to improve the performance of the device by mixing the advantages of each host, for example, when mixing two types of hosts, high efficiency And by mixing one type of host having the effect of low voltage and one type of host having the effect of long life, an organic light emitting device having effects of high efficiency, low voltage and long life can be manufactured.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 발광 스펙트럼의 최대 발광 파장(λ max)이 400 nm 내지 470 nm이다.According to an exemplary embodiment of the present specification, the organic light emitting device has a maximum emission wavelength (λ max ) of an emission spectrum of 400 nm to 470 nm.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 호스트 및 도펀트를 포함하고, 상기 도펀트는 형광 도펀트이다.According to an exemplary embodiment of the present specification, the emission layer includes a host and a dopant, and the dopant is a fluorescent dopant.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 호스트 및 도펀트를 포함하고, 상기 도펀트는 파이렌계 화합물 및 비파이렌계 화합물 중에서 선택되는 1 이상을 포함한다.According to an exemplary embodiment of the present specification, the emission layer includes a host and a dopant, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.
상기 파이렌계 화합물 및 비파이렌계 화합물은 당 업계에서 사용되는 화합물이라면 제한 없이 사용할 수 있으며, 이에만 한정되는 것은 아니다.The pyrene-based compound and the non-pyrene-based compound may be used without limitation as long as they are compounds used in the art, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 비파이렌계 화합물은 보론계 화합물을 포함한다.According to an exemplary embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 호스트 및 도펀트를 포함하고, 상기 호스트는 상기 화학식 2로 표시되는 화합물을 포함하고, 상기 도펀트는 도펀트는 파이렌계 화합물 및 비파이렌계 화합물 중에서 선택되는 1 이상을 포함한다.According to an exemplary embodiment of the present specification, the emission layer includes a host and a dopant, the host includes a compound represented by Formula 2, and the dopant is at least one selected from a pyrene-based compound and a non-pyrene-based compound. includes
본 명세서의 일 실시상태에 따르면, 상기 발광층은 호스트 및 도펀트를 포함하고, 상기 발광층은 호스트: 도펀트를 0.1:99.9 내지 20:80의 중량비로 포함한다.According to an exemplary embodiment of the present specification, the emission layer includes a host and a dopant, and the emission layer includes a host:dopant in a weight ratio of 0.1:99.9 to 20:80.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 상기 캐소드와 상기 발광층 사이에 구비된 전자수송영역을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an electron transport region provided between the cathode and the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 상기 캐소드와 상기 발광층 사이에 구비된 전자수송영역을 포함하고, 상기 전자수송영역은 하기 화학식 3으로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an electron transport region provided between the cathode and the light emitting layer, and the electron transport region includes a compound represented by the following formula (3).
[화학식 3][Formula 3]
Figure PCTKR2021095005-appb-img-000087
Figure PCTKR2021095005-appb-img-000087
상기 화학식 3에 있어서,In Formula 3,
X1은 N 또는 Q101이고, X2는 N 또는 Q102이고, X3는 N 또는 Q103이며, X1 is N or Q101, X2 is N or Q102, X3 is N or Q103,
상기 X1 내지 X3 중 적어도 하나는 N이고,At least one of X1 to X3 is N,
Q101 내지 Q103 및 Q1 내지 Q3는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Q101 to Q103 and Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 전자수송영역은 단환의 6원 헤테로고리 화합물 즉, 트리아진계 유도체, 피리미딘계 유도체 및 피리딘계 유도체라면 제한 없이 사용할 수 있으며, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the electron transport region may be used without limitation as long as it is a monocyclic 6-membered heterocyclic compound, that is, a triazine-based derivative, a pyrimidine-based derivative, and a pyridine-based derivative, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 전자수송영역은 상기 화학식 3으로 표시되는 화합물, 유기 알칼리금속 착화합물, 및 이들의 혼합물을 포함한다. 이 때, 유기 알칼리 금속 착화합물로는 리튬퀴놀레이트, 알루미늄퀴놀레이트일 수 있으나, 이에 한정되지 않으며, 상기 유기 알칼리 금속 착화합물의 함량은 유기물층의 재료 대비 10 내지 90 wt%, 바람직하게는 30 내지 70 wt%로 포함된다.According to an exemplary embodiment of the present specification, the electron transport region includes a compound represented by Chemical Formula 3, an organic alkali metal complex, and a mixture thereof. At this time, the organic alkali metal complex may be lithium quinolate or aluminum quinolate, but is not limited thereto, and the content of the organic alkali metal complex is 10 to 90 wt%, preferably 30 to 70 wt%, based on the material of the organic layer. included in %.
본 명세서의 일 실시상태에 따르면, 상기 전자수송영역은 전자수송층 및 전자조절층을 포함한다.According to an exemplary embodiment of the present specification, the electron transport region includes an electron transport layer and an electron control layer.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 유기물층으로서 전술한 정공수송영역 및 전술한 발광층만을 포함할 수도 있으나, 추가의 유기물층을 더 포함할 수 있다. 예컨대, 추가의 정공주입층, 정공수송층, 전자차단층, 발광층, 정공차단층, 전자수송층, 전자주입층 등을 더 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic light emitting device may include only the hole transport region and the light emitting layer described above as an organic material layer, but may further include an additional organic material layer. For example, it may further include an additional hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and the like.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 추가의 유기물층을 더 포함할 수 있다. 상기 추가의 유기물층은 발광층, 정공주입층, 정공수송층, 정공주입 및 수송층, 전자주입층, 전자수송층, 전자주입 및 수송층, 전자조절층, 전자차단층, 정공차단층 및 정공조절층 중 1 층 이상을 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층물을 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic light emitting device may further include an additional organic material layer. The additional organic material layer includes at least one of a light emitting layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron control layer, an electron blocking layer, a hole blocking layer, and a hole control layer. can have However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
또 하나의 실시상태에 있어서, 유기 발광 소자는 기판 상에 애노드, 1층 이상의 유기물층 및 캐소드가 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. In another exemplary embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
또 하나의 실시상태에 있어서, 유기 발광 소자는 기판 상에 캐소드, 1층 이상의 유기물층 및 애노드가 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. In another exemplary embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
본 명세서의 유기 발광 소자는 상기 유기물층 중 발광층에 인접하는 층이 상기 화학식 1로 표시되는 화합물을 포함하고, 상기 발광층이 상기 화학식 2로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술 분야에 알려져 있는 재료와 방법으로 제조될 수 있다.The organic light emitting device of the present specification is known in the art, except that the layer adjacent to the light emitting layer of the organic material layer includes the compound represented by Formula 1, and the light emitting layer includes the compound represented by Formula 2 It can be manufactured with materials and methods.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 물리 증착 방법(PVD: physical Vapor Deposition)을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate. It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Laid-Open No. 2003/012890). However, the manufacturing method is not limited thereto.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO 2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is generally preferable to facilitate hole injection into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO 2/Al, Mg/Ag과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF/Al or LiO 2 /Al, and a multi-layered material such as Mg/Ag, but is not limited thereto.
상기 음극 위에 추가로 전극의 보호를 위한 캡핑층(capping)층을 형성할 수 있으며, 상기 캡핑층 물질은 당 기술분야에 사용되는 재료를 적절하게 사용할 수 있다.A capping layer for protecting the electrode may be additionally formed on the cathode, and materials used in the art may be appropriately used for the capping layer material.
상기 정공주입층은 정공 주입 물질로는 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer for injecting holes from the electrode as a hole injection material, and has an ability to transport holes as a hole injection material, so that it has an excellent hole injection effect with respect to the hole injection effect at the anode, the light emitting layer or the light emitting material. , a compound that prevents the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them to the light emitting layer. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
상기 전자차단층은 정공주입층으로부터 주입된 정공이 발광층을 지나 전자주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층으로, 공지의 재료를 사용하여 발광층과 전자주입층의 사이에 적절한 부분에 형성될 수 있다.The electron blocking layer is a layer that can improve the life and efficiency of the device by preventing the holes injected from the hole injection layer from entering the electron injection layer through the emission layer. It may be formed in an appropriate portion between.
상기 발광층의 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 본 명세서의 유기 발광 소자가 상기 화학식 2로 표시되는 화합물을 포함하는 발광층 이외에, 추가의 발광층을 포함하는 경우, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq 3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤조티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. The light emitting material of the light emitting layer is a material capable of emitting light in the visible ray region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and the organic light emitting device of the present specification includes a compound represented by Formula 2 In the case of including an additional light emitting layer in addition to the light emitting layer, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but is not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로 고리 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로 고리 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic compound containing carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
상기 발광층과 상기 전자수송층 사이에는 전자조절층이 추가로 구비될 수 있다. 전자조절층 물질은 당 기술분야에 사용되는 재료를 적절하게 사용할 수 있다.An electron control layer may be further provided between the light emitting layer and the electron transport layer. As the material for the electron control layer, any material used in the art may be appropriately used.
상기 전자수송층의 전자 수송 물질로는 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로, 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al착물; Alq 3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer, and the electron transport material is a material that can receive electrons from the cathode and transfer them to the light emitting layer. Materials with high mobility are suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.
상기 정공차단층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다.The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.
본 명세서의 일 실시상태에 따른 구조는 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다.The structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.
상기 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 명세서를 예시하기 위한 것이며, 본 명세서의 범위가 이들에 의하여 한정되는 것은 아니다.The manufacturing of the organic light emitting device will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.
제조예 (실시 BH 의 합성)Preparation Example (Synthesis of Example BH)
Figure PCTKR2021095005-appb-img-000088
Figure PCTKR2021095005-appb-img-000088
반응물(1eq), Trifluoromethanesulfonic acid (cat.)을 C 6D 6 (반응물 대비 질량비 10~50 배)에 넣고 70℃에서 10분 내지 100분사이에서 교반하였다. 반응 종료 후 D 2O (excess)를 넣고 30분 교반한 뒤 트리메틸아민(trimethylamine) (excess)를 적가하였다. 반응액을 분액 깔대기에 옮기고, 물과 클로로포름으로 추출하였다. 추출액을 MgSO 4로 건조 후, 톨루엔으로 가열하여 재결정하여 하기 표 1 및 표 2의 생성물을 수득하였다.The reactant (1eq), Trifluoromethanesulfonic acid (cat.) was added to C 6 D 6 (10-50 times the mass ratio of the reactant) and stirred at 70° C. for 10 to 100 minutes. After completion of the reaction, D 2 O (excess) was added and stirred for 30 minutes, followed by dropwise addition of trimethylamine (excess). The reaction solution was transferred to a separatory funnel, and extracted with water and chloroform. The extract was dried over MgSO 4 , and recrystallized by heating with toluene to obtain the products shown in Tables 1 and 2 below.
Figure PCTKR2021095005-appb-img-000089
Figure PCTKR2021095005-appb-img-000089
Figure PCTKR2021095005-appb-img-000090
Figure PCTKR2021095005-appb-img-000090
Figure PCTKR2021095005-appb-img-000091
Figure PCTKR2021095005-appb-img-000091
Figure PCTKR2021095005-appb-img-000092
Figure PCTKR2021095005-appb-img-000092
Figure PCTKR2021095005-appb-img-000093
Figure PCTKR2021095005-appb-img-000093
Figure PCTKR2021095005-appb-img-000094
Figure PCTKR2021095005-appb-img-000094
각 생성물은 반응시간에 따라 중수소치환의 정도가 다르며 최대 m/z (M+) 값에 따라 치환율을 결정하였다.Each product had a different degree of deuterium substitution depending on the reaction time, and the substitution rate was determined according to the maximum m/z (M+) value.
상기 반응물은 KR1964435, KR1899728, KR1975945, KR2018-0098122, KR2018-0102937, KR2018-0103352 와 같은 자사 선행문헌을 참고하여 합성하였다. 또한 상기의 생성물에 대한 중수소 치환은 KR1538534 의 선행문헌을 참고하였다.The reactants were synthesized with reference to their prior literature such as KR1964435, KR1899728, KR1975945, KR2018-0098122, KR2018-0102937, KR2018-0103352. In addition, for the deuterium substitution for the above product, reference was made to the prior literature of KR1538534.
Figure PCTKR2021095005-appb-img-000095
Figure PCTKR2021095005-appb-img-000095
Figure PCTKR2021095005-appb-img-000096
Figure PCTKR2021095005-appb-img-000096
Figure PCTKR2021095005-appb-img-000097
Figure PCTKR2021095005-appb-img-000097
Figure PCTKR2021095005-appb-img-000098
Figure PCTKR2021095005-appb-img-000098
각 생성물은 반응시간에 따라 중수소치환의 정도가 다르며 최대 m/z (M+) 값에 따라 치환율을 결정하였다.Each product had a different degree of deuterium substitution depending on the reaction time, and the substitution rate was determined according to the maximum m/z (M+) value.
상기 반응물은 KR 1994238 B1, KR 1670193 B1, KR1754445 B1, KR 1368164 B1 와 같은 자사 선행문헌을 참고하여 합성하였다. 또한 상기의 생성물에 대한 중수소 치환은 KR 1538534 B1 의 선행문헌을 참고하였다. The reactants were synthesized with reference to their prior literatures such as KR 1994238 B1, KR 1670193 B1, KR1754445 B1, and KR 1368164 B1. In addition, for the substitution of deuterium for the above product, the prior literature of KR 1538534 B1 was referred.
또한, 상기 선행문헌을 참고하여 중수소 치환율이 각각 40%, 65%인 화합물 1-21 내지 1-22 와 BH3(중수소 치환율 0%), BH4 (중수소 치환율 25%) 및 BH5 (중수소 치환율 35%)을 합성하여 중수소 치환율이 다른 화합물과의 비교 실험도 실행하였다.In addition, with reference to the preceding literature, compounds 1-21 to 1-22 having deuterium substitution rates of 40% and 65%, respectively, and BH3 (deuterium substitution rate 0%), BH4 (deuterium substitution rate 25%) and BH5 (deuterium substitution rate 35%) was synthesized and a comparative experiment with compounds having different deuterium substitution rates was also performed.
Figure PCTKR2021095005-appb-img-000099
Figure PCTKR2021095005-appb-img-000099
상기 표 1 및 2의 생성물, 화합물 1-21 및 1-22는 JP 4070676 B2, KR 1477844 B1, US 6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082 B2, JP 5015459 B2, KR 1979037 B1, KR 1550351 B1, KR 1503766 B1, KR 0826364 B1, KR 0749631 B1, KR 1115255 B1 와 같은 선행문헌을 참고하여 합성하였다. 또한, 상기 표 1 및 2에서 합성된 생성물에 결합된 중수소(-D)는 표시된 위치에 결합될 수 있는 것을 의미하며, 반드시 표시된 위치에 결합되어야 하는 것을 의미하는 것이 아니다.The products of Tables 1 and 2, compounds 1-21 and 1-22 are JP 4070676 B2, KR 1477844 B1, US 6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082 B2, JP 5015459 B2, KR 1979037 B1, KR 1550351 B1, KR 1503766 B1, KR 0826364 B1, KR 0749631 B1, KR 1115255 B1 were synthesized with reference to prior literature. In addition, deuterium (-D) bound to the products synthesized in Tables 1 and 2 means that it can be bound to the indicated position, and does not necessarily mean that it must be bound to the indicated position.
또한 하기 정공수송영역에 포함되는 상기 화학식 1로 표시되는 화합물인 하기 화합물 3-1 내지 3-18은 JP 2015-530364 A, US 5840217 A, WO2013-120577 A, KR 2016-0035610 A 를 참고하여 합성하였다. In addition, the following compounds 3-1 to 3-18, which are compounds represented by Formula 1 included in the hole transport region, are synthesized with reference to JP 2015-530364 A, US 5840217 A, WO2013-120577 A, KR 2016-0035610 A. did.
Figure PCTKR2021095005-appb-img-000100
Figure PCTKR2021095005-appb-img-000100
<비교예 1-1> 유기 발광 소자의 제조<Comparative Example 1-1> Preparation of organic light emitting device
양극으로서 ITO/Ag/ITO가 70/1000/70Å증착된 기판을 50mm × 50mm × 0.5mm크기로 잘라서 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터(Filter)로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다.A substrate on which 70/1000/70 Å of ITO/Ag/ITO was deposited as an anode was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.
이렇게 준비된 양극 위에 HI-1을 50Å의 두께로 열 진공 증착하여 정공주입층을 형성하고, 그 위에 정공을 수송하는 물질인 HT1을 두께 1150Å로 진공증착하여 정공수송층을 형성하였다. 그 다음에 EB1 (150Å)를 이용하여 제 정공조절층을 형성하고 그 다음에 BH1 과 도판트 BD1 (2중량%) 을 360Å의 두께로 진공 증착하여 발광층을 형성하였다. 그 후 HB1을 50Å증착하여 전자조절층을 형성하고, 화합물 ET1와 Liq를 5:5 (질량비) 로 혼합하여 두께 250Å의 전자수송층을 형성하였다. 순차적으로 50Å두께의 마그네슘과 리튬 플루오라이드(LiF)을 전자주입층<EIL>으로 성막한 후 음극으로 마그네슘과 은(1:4)로 200Å형성시킨 후 CP1을 600 Å증착하여 소자를 완성하였다. 상기의 과정에서 유기물의 증착속도는 1 Å/sec를 유지하였다.On the prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, a hole control layer was formed using EB1 (150 Å), and then BH1 and a dopant BD1 (2 wt %) were vacuum-deposited to a thickness of 360 Å to form a light emitting layer. Thereafter, HB1 was deposited by 50 Å to form an electron control layer, and the compound ET1 and Liq were mixed at 5:5 (mass ratio) to form an electron transport layer having a thickness of 250 Å. After sequentially forming a film of 50 Å thick magnesium and lithium fluoride (LiF) as an electron injection layer <EIL>, 200 Å of magnesium and silver (1:4) were formed as an anode, and then CP1 was deposited by 600 Å to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.
Figure PCTKR2021095005-appb-img-000101
Figure PCTKR2021095005-appb-img-000101
Figure PCTKR2021095005-appb-img-000102
Figure PCTKR2021095005-appb-img-000102
<비교예 1-2 내지 1-15 및 실시예 1-1 내지 1-43><Comparative Examples 1-2 to 1-15 and Examples 1-1 to 1-43>
상기 비교예 1-1 에서 발광층의 호스트로 BH1 대신 하기 표 3의 화합물을 각각 사용하고, 정공조절층으로 EB1 대신 하기 표 3의 화합물을 각각 사용하는 것을 제외하고는 상기 비교예 1-1과 동일하게 유기 발광 소자를 제조하였고, 상기 비교예 1-1 내지 1-15 및 실시예 1-1 내지 1-43에서 제조된 유기 발광 소자의 구조를 하기 표 3에 나타내었고, 하기 표 4는 상기 비교예 1-1 내지 1-15 및 실시예 1-1 내지 1-43를 20mA/cm 2의 전류밀도에서 구동전압, 발광 효율, 및 초기 휘도 대비 95%가 되는 시간(LT95)을 측정한 결과이다.The same as in Comparative Example 1-1, except that in Comparative Example 1-1, the compound of Table 3 was used instead of BH1 as the host of the light emitting layer, and the compound of Table 3 was used instead of EB1 as the hole control layer. The organic light emitting device was prepared in the above-mentioned manner, and the structures of the organic light emitting devices prepared in Comparative Examples 1-1 to 1-15 and Examples 1-1 to 1-43 are shown in Table 3 below, and Table 4 below is shown in the comparative examples. Examples 1-1 to 1-15 and Examples 1-1 to 1-43 are the results of measuring the driving voltage, luminous efficiency, and time (LT95) to 95% of the initial luminance at a current density of 20 mA/cm 2 .
Figure PCTKR2021095005-appb-img-000103
Figure PCTKR2021095005-appb-img-000103
Figure PCTKR2021095005-appb-img-000104
Figure PCTKR2021095005-appb-img-000104
Figure PCTKR2021095005-appb-img-000105
Figure PCTKR2021095005-appb-img-000105
Figure PCTKR2021095005-appb-img-000106
Figure PCTKR2021095005-appb-img-000106
Figure PCTKR2021095005-appb-img-000107
Figure PCTKR2021095005-appb-img-000107
Figure PCTKR2021095005-appb-img-000108
Figure PCTKR2021095005-appb-img-000108
Figure PCTKR2021095005-appb-img-000109
Figure PCTKR2021095005-appb-img-000109
Figure PCTKR2021095005-appb-img-000110
Figure PCTKR2021095005-appb-img-000110
Figure PCTKR2021095005-appb-img-000111
Figure PCTKR2021095005-appb-img-000111
Figure PCTKR2021095005-appb-img-000112
Figure PCTKR2021095005-appb-img-000112
Figure PCTKR2021095005-appb-img-000113
Figure PCTKR2021095005-appb-img-000113
상기 표 3 및 4에 있어서, 본 명세서의 일 실시상태에 따른 유기 발광 소자는 청색 유기 전계 발광소자의 정공수송영역에 적용되는 화학식 1 및 발광층의 호스트로 적용되는 화학식 2의 화합물을 사용함으로써 발광층으로의 우수한 정공 주입 및 수송을 능력을 보였다. 또한, 화학적 구조에 따른 유기 발광 소자의 정공과 전자의 균형을 통하여 본 명세서에 따른 유기 발광 소자는 화학식 1 또는 화학식 2를 각각 포함하는 유기 발광 소자 보다 효율, 구동전압, 안정성 면에서 우수한 특성을 나타내었다.In Tables 3 and 4, the organic light emitting device according to an exemplary embodiment of the present specification is a light emitting layer by using the compound of Formula 1 applied to the hole transport region of the blue organic light emitting device and Formula 2 applied as a host of the light emitting layer. showed excellent hole injection and transport ability. In addition, through the balance of holes and electrons of the organic light emitting device according to the chemical structure, the organic light emitting device according to the present specification exhibits superior characteristics in terms of efficiency, driving voltage, and stability than the organic light emitting device including Formula 1 or Formula 2, respectively. It was.
특히, 상기 화학식 2의 중수소 치환율에 따른 소자 특성에 대한 결과도 상기 표3 내지 표4 의 결과를 보면 관찰할 수 있다. 화합물 1-6의 중수소 치환율이 각각 미치환(0%), 20%, 35%인 화합물을 사용하는 비교예 1-11 내지 1-13는 중수소 치환율이 40% 이상인 화합물을 사용하는 실시예 1-6, 1-42 및 1-43 대비 현저히 낮은 수명을 보여주고 있고, 중수소 치환에 따른 수명 증가 효과가 미비함을 알 수 있다. 반면, 상기 화학식 2의 중수소 치환율이 40% 이상인 실시예 1-6, 1-42 및 1-43은 비교예 1-11 내지 1-13보다 소자의 수명이 크게 향상되었으며, 상기 화학식 2의 중수소 치환율의 40% 이상이어야 소자의 수명이 크게 향상됨을 알 수있다.In particular, the results of the device characteristics according to the deuterium substitution rate of Formula 2 can also be observed by looking at the results of Tables 3 to 4. Comparative Examples 1-11 to 1-13 using a compound in which the deuterium substitution rate of Compound 1-6 is unsubstituted (0%), 20%, and 35%, respectively, is Example 1- using a compound having a deuterium substitution rate of 40% or more It can be seen that 6, 1-42 and 1-43 show a significantly lower lifespan, and the effect of increasing the lifespan according to deuterium substitution is insignificant. On the other hand, in Examples 1-6, 1-42, and 1-43 in which the deuterium substitution rate of Chemical Formula 2 is 40% or more, the lifespan of the device is significantly improved compared to Comparative Examples 1-11 to 1-13, and the deuterium substitution rate of Chemical Formula 2 is It can be seen that the lifetime of the device is greatly improved when it is more than 40% of
또한, 상기 실시예 1-42 및 1-43과 비교예 1-14 및 1-15를 비교하였을 때, 상기 화학식 2의 중수소 치환율이 40% 이상인 실시예 1-42 및 1-43의 수명이 크게 향상되었고, 효율 및 구동 전압도 우수함을 알 수 있다.In addition, when comparing Examples 1-42 and 1-43 with Comparative Examples 1-14 and 1-15, the lifespan of Examples 1-42 and 1-43 in which the deuterium substitution rate of Chemical Formula 2 was 40% or more was significantly longer. improved, and it can be seen that the efficiency and the driving voltage are also excellent.
<비교예 2-1> 유기 발광 소자의 제조<Comparative Example 2-1> Preparation of organic light emitting device
양극으로서 ITO/Ag/ITO가 70/1000/70Å증착된 기판을 50mm × 50mm × 0.5mm크기로 잘라서 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터(Filter)로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다.A substrate on which 70/1000/70 Å of ITO/Ag/ITO was deposited as an anode was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.
이렇게 준비된 양극 위에 HI-1을 50Å의 두께로 열 진공 증착하여 정공주입층을 형성하고, 그 위에 정공을 수송하는 물질인 HT1을 두께 1150Å로 진공증착하여 정공수송층을 형성하였다. 그 다음에 EB1 (150Å)를 이용하여 제 정공조절층을 형성하고 그 다음에 BH1 과 도판트 BD2 (2중량%) 을 360Å의 두께로 진공 증착하여 발광층을 형성하였다. 그 후 HB1을 50Å증착하여 전자조절층을 형성하고, 화합물 ET1와 Liq를 5:5 (질량비) 로 혼합하여 두께 250Å의 전자수송층을 형성하였다. 순차적으로 50Å두께의 마그네슘과 리튬 플루오라이드(LiF)을 전자주입층<EIL>으로 성막한 후 음극으로 마그네슘과 은(1:4)로 200Å형성시킨 후 CP1을 600 Å증착하여 소자를 완성하였다. 상기의 과정에서 유기물의 증착속도는 1 Å/sec를 유지하였다.On the prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, a hole control layer was formed using EB1 (150 Å), and then BH1 and dopant BD2 (2 wt %) were vacuum-deposited to a thickness of 360 Å to form a light emitting layer. Thereafter, HB1 was deposited by 50 Å to form an electron control layer, and the compound ET1 and Liq were mixed at 5:5 (mass ratio) to form an electron transport layer having a thickness of 250 Å. After sequentially forming a film of 50 Å thick magnesium and lithium fluoride (LiF) as an electron injection layer <EIL>, 200 Å of magnesium and silver (1:4) were formed as an anode, and then CP1 was deposited by 600 Å to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.
Figure PCTKR2021095005-appb-img-000114
Figure PCTKR2021095005-appb-img-000114
Figure PCTKR2021095005-appb-img-000115
Figure PCTKR2021095005-appb-img-000115
<비교예 2-2 내지 2-10 및 실시예 2-1 내지 2-41><Comparative Examples 2-2 to 2-10 and Examples 2-1 to 2-41>
상기 비교예 2-1 에서 발광층의 호스트로 BH1 대신 하기 표 5의 화합물을 각각 사용하고, 정공조절층으로 EB1 대신 하기 표 5의 화합물을 각각 사용하는 것을 제외하고는 상기 비교예 2-1과 동일하게 유기 발광 소자를 제조하였고, 상기 비교예 2-1 내지 2-10 및 실시예 2-1 내지 2-41에서 제조된 유기 발광 소자의 구조를 하기 표 5에 나타내었고, 하기 표 6은 상기 비교예 2-1 내지 2-10 및 실시예 2-1 내지 2-41를 20mA/cm 2의 전류밀도에서 구동전압, 발광 효율, 및 초기 휘도 대비 95%가 되는 시간(LT95)을 측정한 결과이다.The same as in Comparative Example 2-1, except that in Comparative Example 2-1, the compound of Table 5 was used instead of BH1 as the host of the light emitting layer, and the compound of Table 5 was used instead of EB1 as the hole control layer. The organic light emitting diodes were prepared in the above manner, and the structures of the organic light emitting diodes prepared in Comparative Examples 2-1 to 2-10 and Examples 2-1 to 2-41 are shown in Table 5 below, and Table 6 below is Examples 2-1 to 2-10 and Examples 2-1 to 2-41 at a current density of 20 mA/cm 2 The driving voltage, luminous efficiency, and time (LT95) to be 95% compared to the initial luminance are measured results .
Figure PCTKR2021095005-appb-img-000116
Figure PCTKR2021095005-appb-img-000116
Figure PCTKR2021095005-appb-img-000117
Figure PCTKR2021095005-appb-img-000117
Figure PCTKR2021095005-appb-img-000118
Figure PCTKR2021095005-appb-img-000118
Figure PCTKR2021095005-appb-img-000119
Figure PCTKR2021095005-appb-img-000119
Figure PCTKR2021095005-appb-img-000120
Figure PCTKR2021095005-appb-img-000120
Figure PCTKR2021095005-appb-img-000121
Figure PCTKR2021095005-appb-img-000121
Figure PCTKR2021095005-appb-img-000122
Figure PCTKR2021095005-appb-img-000122
Figure PCTKR2021095005-appb-img-000123
Figure PCTKR2021095005-appb-img-000123
Figure PCTKR2021095005-appb-img-000124
Figure PCTKR2021095005-appb-img-000124
Figure PCTKR2021095005-appb-img-000125
Figure PCTKR2021095005-appb-img-000125
상기 표 3 내지 6에 있어서, 본 명세서의 일 실시상태에 따른 유기 발광 소자는 청색 유기 전계 발광소자의 정공수송영역에 적용되는 화학식 1 및 발광층의 호스트로 적용되는 화학식 2의 화합물을 사용함으로써 발광층으로의 우수한 정공 주입 및 수송을 능력을 보였다. 또한, 화학적 구조에 따른 유기 발광 소자의 정공과 전자의 균형을 통하여 본 명세서에 따른 유기 발광 소자는 화학식 1 또는 화학식 2를 각각 포함하는 유기 발광 소자 보다 효율, 구동전압, 안정성 면에서 우수한 특성을 나타내었다.In Tables 3 to 6, the organic light emitting device according to an exemplary embodiment of the present specification is a light emitting layer by using the compound of Formula 1 applied to the hole transport region of the blue organic light emitting device and Formula 2 applied as a host of the light emitting layer. showed excellent hole injection and transport ability. In addition, through the balance of holes and electrons of the organic light emitting device according to the chemical structure, the organic light emitting device according to the present specification exhibits superior characteristics in terms of efficiency, driving voltage, and stability than the organic light emitting device including Formula 1 or Formula 2, respectively. It was.
상기 실시예 1-1 내지 1-38, 1-42, 1-43, 및 2-1 내지 2-38은 정공수송층으로 상기 화학식 1의 화합물과 발광층의 호스트로 상기 화학식 2의 화합물을 단일로 사용하여 소자를 제작하였다. 소자의 구성은 상기 화학식 1에 해당하는 다양한 정공조절층 및 상기 화학식 2에 해당하는 다양한 청색 호스트, 청색 형광 도판트 중 BD1 또는 BD2가 적용될 수 있음을 보여주고 있다. 또한 실시예 1-39 내지 1-41 및 2-39 내지 2-41은 화학식 2에 해당하는 호스트의 2종이 혼합호스트로 사용되어 소자의 성능이 향상될 수 있음을 나타내고 있다.In Examples 1-1 to 1-38, 1-42, 1-43, and 2-1 to 2-38, the compound of Formula 1 as the hole transport layer and the compound of Formula 2 as the host of the light emitting layer are used singly Thus, a device was fabricated. The device configuration shows that BD1 or BD2 of various hole control layers corresponding to Chemical Formula 1 and various blue hosts and blue fluorescent dopants corresponding to Chemical Formula 2 can be applied. Also, Examples 1-39 to 1-41 and 2-39 to 2-41 show that two types of hosts corresponding to Formula 2 are used as mixed hosts to improve device performance.
상기 비교예 1-1 내지 1-6, 1-11 내지 1-13 및 2-1 내지 2-6은 본 명세서의 일 실시상태에 따른 화합물 1 및 2의 조합이 아닌 화합물로 제작된 소자의 결과이며 발광층의 호스트는 아릴계열의 안트라센이 사용되었다. 해당 경우 모두 높은 전압, 낮은 효율, 낮은 수명을 나타내며 소자의 성능이 낮음을 나타낸다. Comparative Examples 1-1 to 1-6, 1-11 to 1-13, and 2-1 to 2-6 are results of devices manufactured with compounds other than the combination of compounds 1 and 2 according to an exemplary embodiment of the present specification and an aryl-based anthracene was used as the host of the light emitting layer. In all of these cases, high voltage, low efficiency, and low lifetime indicate poor performance of the device.
상기 비교예 1-7, 1-8, 1-14, 1-15, 2-7 및 2-8은 상기 화학식 1에 대응되는 정공조절층만을 적용한 결과로 비교예 1-1 내지 1-6, 1-11 내지 1-13 및 2-1 내지 2-6 대비 소폭의 구동전압 하락 경향성을 관찰할 수 있지만 전반적인 소자 성능 개선은 이루어지지 않음을 볼 수 있었다. 또한, 상기 비교예 1-9, 1-10, 2-9 및 2-10은 상기 화학식 2에 해당하는 청색 호스트만을 적용시킨 결과로써 비교예 1-1 내지 1-6, 1-11 내지 1-13 및 2-1 내지 2-6 대비 전반적인 수명의 상승을 관찰할 수 있다. Comparative Examples 1-7, 1-8, 1-14, 1-15, 2-7, and 2-8 are the results of applying only the hole control layer corresponding to Chemical Formula 1, and Comparative Examples 1-1 to 1-6, It can be seen that a slight decrease in driving voltage compared to 1-11 to 1-13 and 2-1 to 2-6 can be observed, but overall device performance is not improved. In addition, Comparative Examples 1-9, 1-10, 2-9 and 2-10 are the results of applying only the blue host corresponding to Chemical Formula 2, and Comparative Examples 1-1 to 1-6, 1-11 to 1- 13 and 2-1 to 2-6 compared to the overall lifespan can be observed.
상기 비교예 1-1 내지 1-15 및 2-1 내지 2-10 대비 실시예 1-1 내지 1-43 및 2-1 내지 2-41은 본 명세서의 화학식 1 및 2의 조합으로 소자의 캐리어, 특히 정공이 호스트내로의 주입이 용이하여 소자의 밸런스를 잡아주는 역할을 하며 소자 성능의 전반적 개선이 가능함을 보여주고 있다. In Comparative Examples 1-1 to 1-15 and 2-1 to 2-10, Examples 1-1 to 1-43 and 2-1 to 2-41 are a combination of Chemical Formulas 1 and 2 of the present specification, and the carrier of the device , in particular, it is easy to inject holes into the host, so it plays a role in balancing the device and shows that the overall performance of the device can be improved.
상기 실시예 2-1 내지 실시예 2-41은 BD2 및 본 명세서의 화학식 1 및 2의 조합을 적용시킨 소자의 결과로써 다양한 타입의 청색도판트를 도입하였을 때도 해당 조합의 소자 밸런스의 우수함을 관찰할 수 있다.In Examples 2-1 to 2-41, it was observed that the device balance of the corresponding combination was excellent even when various types of blue dopants were introduced as a result of the device to which the combination of BD2 and Formulas 1 and 2 of the present specification was applied can do.

Claims (23)

  1. 애노드;anode;
    캐소드;cathode;
    상기 애노드와 상기 캐소드 사이에 구비된 발광층; 및a light emitting layer provided between the anode and the cathode; and
    상기 발광층과 상기 애노드 사이에 구비된 2층 이상의 유기물층을 포함하는 정공수송영역을 포함하는 유기 발광 소자로서,An organic light emitting device including a hole transport region including two or more organic material layers provided between the light emitting layer and the anode,
    상기 유기물층 중 발광층에 접하는 유기물층은 하기 화학식 1로 표시되는 화합물을 포함하고,Among the organic material layers, the organic material layer in contact with the light emitting layer contains a compound represented by the following formula (1),
    상기 발광층은 하기 화학식 2로 표시되는 화합물을 포함하는 유기 발광 소자:The light emitting layer is an organic light emitting device including a compound represented by Formula 2:
    [화학식 1][Formula 1]
    Figure PCTKR2021095005-appb-img-000126
    Figure PCTKR2021095005-appb-img-000126
    상기 화학식 1에 있어서,In Formula 1,
    R8 및 R9 중 어느 하나는 하기 화학식 a로 표시되는 기이고, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 치환 또는 비치환된 탄화수소고리를 형성할 수 있으며,Any one of R8 and R9 is a group represented by the following formula (a), and among R8 and R9, a group other than a group represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring can form,
    [화학식 a][Formula a]
    Figure PCTKR2021095005-appb-img-000127
    Figure PCTKR2021095005-appb-img-000127
    상기 화학식 a에 있어서,In the formula (a),
    L1 내지 L3는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L1 to L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar1 and Ar2 are the same as or different from each other, and each independently deuterium; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    l1 내지 l3는 각각 1 내지 3의 정수이고,l1 to l3 are each an integer of 1 to 3,
    상기 l1이 2 이상인 경우, 상기 2 이상의 L1은 서로 같거나 상이하며,When the l1 is 2 or more, the 2 or more L1s are the same as or different from each other,
    상기 l2가 2 이상인 경우, 상기 2 이상의 L2는 서로 같거나 상이하고,When the l2 is 2 or more, the 2 or more L2s are the same as or different from each other,
    상기 l3가 2 이상인 경우, 상기 2 이상의 L3는 서로 같거나 상이하며,When the l3 is 2 or more, the 2 or more L3 are the same as or different from each other,
    Figure PCTKR2021095005-appb-img-000128
    는 상기 화학식 1의 R8 또는 R9에 결합되는 부위를 의미하고,
    Figure PCTKR2021095005-appb-img-000128
    means a site bonded to R8 or R9 of Formula 1,
    [화학식 2][Formula 2]
    Figure PCTKR2021095005-appb-img-000129
    Figure PCTKR2021095005-appb-img-000129
    상기 화학식 2에 있어서,In Formula 2,
    G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,At least one of G1 to G10 is a group represented by the following formula (b), the rest are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    [화학식 b][Formula b]
    Figure PCTKR2021095005-appb-img-000130
    Figure PCTKR2021095005-appb-img-000130
    상기 화학식 b에 있어서,In the formula (b),
    A 및 B는 서로 같거나 상이하고 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리이며,A and B are the same as or different from each other and a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic ring,
    L4는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L4 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    l4는 1 내지 3의 정수이며,l4 is an integer from 1 to 3,
    상기 l4가 2 이상인 경우, 상기 2 이상의 L4는 서로 같거나 상이하고,When the l4 is 2 or more, the 2 or more L4s are the same as or different from each other,
    Figure PCTKR2021095005-appb-img-000131
    는 상기 화학식 2의 G1 내지 G10 중 적어도 하나에 결합되는 부위를 의미하며,
    Figure PCTKR2021095005-appb-img-000131
    means a site bonded to at least one of G1 to G10 of Formula 2,
    상기 화학식 2의 중수소 치환율은 40 % 내지 100%이다.The deuterium substitution rate of Formula 2 is 40% to 100%.
  2. 청구항 1에 있어서, 상기 화학식 2의 중수소 치환율은 40 % 내지 99%인 것인 유기 발광 소자.The organic light emitting diode of claim 1, wherein the deuterium substitution ratio of Formula 2 is 40% to 99%.
  3. 청구항 1에 있어서, 상기 화학식 1의 중수소 치환율은 1 % 내지 100%인 것인 유기 발광 소자.The organic light emitting diode of claim 1, wherein the deuterium substitution ratio of Chemical Formula 1 is 1% to 100%.
  4. 청구항 1에 있어서, 상기 R8 및 R9 중 어느 하나는 상기 화학식 a로 표시되는 기이고, 상기 R8 및 R9 중 상기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R7 및 R10 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 상기 R8 및 R9 중 하기 화학식 a로 표시되는 기가 아닌 기, R1 내지 R6, R7, 및 R10 내지 R18 중 인접한 기는 서로 결합하여, 탄소수 6 내지 20의 다환의 방향족 탄화수소고리를 형성하는 것인 유기 발광 소자.The method according to claim 1, wherein any one of R8 and R9 is a group represented by the formula (a), and among R8 and R9, a group other than the group represented by the formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, , each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a group other than a group represented by the following formula (a) among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are mutually exclusive An organic light emitting device that combines to form a polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  5. 청구항 1에 있어서, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 중수소, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기인 것인 유기 발광 소자.The method according to claim 1, wherein L1 to L3 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or deuterium, or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
  6. 청구항 1에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 중수소로 치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬실릴기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 중수소, 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 및 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1이상으로 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기인 것인 유기 발광 소자.The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with deuterium, and a carbon number A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from a linear or branched alkylsilyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or at least one selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms and a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. .
  7. 청구항 1에 있어서, 상기 G1 내지 G10 중 적어도 하나는 하기 화학식 b로 표시되는 기이고, 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기인 것인 유기 발광 소자.The method according to claim 1, wherein at least one of G1 to G10 is a group represented by the following formula (b), the rest are the same as or different from each other, each independently hydrogen; heavy hydrogen; Or an organic light emitting device that is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more selected from a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium.
  8. 청구항 1에 있어서, 상기 L4는 직접결합; 또는 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기인 것인 유기 발광 소자.The method according to claim 1, wherein L4 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  9. 청구항 1에 있어서, 상기 A 및 B는 서로 같거나 상이하고, 각각 독립적으로 중수소, 및 중수소로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기 중에서 선택되는 1 이상으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 중수소로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리인 것인 유기 발광 소자.The method according to claim 1, wherein A and B are the same as or different from each other, and each independently is substituted or unsubstituted with one or more selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium. a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or an organic light-emitting device that is a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms unsubstituted or substituted with deuterium.
  10. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나인 것인 유기 발광 소자:The organic light-emitting device of claim 1, wherein Chemical Formula 1 is any one selected from the following compounds:
    Figure PCTKR2021095005-appb-img-000132
    Figure PCTKR2021095005-appb-img-000132
    Figure PCTKR2021095005-appb-img-000133
    Figure PCTKR2021095005-appb-img-000133
    Figure PCTKR2021095005-appb-img-000134
    Figure PCTKR2021095005-appb-img-000134
    Figure PCTKR2021095005-appb-img-000135
    Figure PCTKR2021095005-appb-img-000135
    Figure PCTKR2021095005-appb-img-000136
    Figure PCTKR2021095005-appb-img-000136
    Figure PCTKR2021095005-appb-img-000137
    Figure PCTKR2021095005-appb-img-000137
    Figure PCTKR2021095005-appb-img-000138
    Figure PCTKR2021095005-appb-img-000138
    Figure PCTKR2021095005-appb-img-000139
    Figure PCTKR2021095005-appb-img-000139
    Figure PCTKR2021095005-appb-img-000140
    Figure PCTKR2021095005-appb-img-000140
    Figure PCTKR2021095005-appb-img-000141
    Figure PCTKR2021095005-appb-img-000141
    Figure PCTKR2021095005-appb-img-000142
    Figure PCTKR2021095005-appb-img-000142
    Figure PCTKR2021095005-appb-img-000143
    Figure PCTKR2021095005-appb-img-000143
    Figure PCTKR2021095005-appb-img-000144
    Figure PCTKR2021095005-appb-img-000144
    Figure PCTKR2021095005-appb-img-000145
    Figure PCTKR2021095005-appb-img-000145
    Figure PCTKR2021095005-appb-img-000146
    Figure PCTKR2021095005-appb-img-000146
    Figure PCTKR2021095005-appb-img-000147
    Figure PCTKR2021095005-appb-img-000147
    Figure PCTKR2021095005-appb-img-000148
    Figure PCTKR2021095005-appb-img-000148
    Figure PCTKR2021095005-appb-img-000149
    Figure PCTKR2021095005-appb-img-000149
    Figure PCTKR2021095005-appb-img-000150
    Figure PCTKR2021095005-appb-img-000150
    Figure PCTKR2021095005-appb-img-000151
    Figure PCTKR2021095005-appb-img-000151
    Figure PCTKR2021095005-appb-img-000152
    Figure PCTKR2021095005-appb-img-000152
    Figure PCTKR2021095005-appb-img-000153
    Figure PCTKR2021095005-appb-img-000153
    Figure PCTKR2021095005-appb-img-000154
    Figure PCTKR2021095005-appb-img-000154
    Figure PCTKR2021095005-appb-img-000155
    Figure PCTKR2021095005-appb-img-000155
    Figure PCTKR2021095005-appb-img-000156
    Figure PCTKR2021095005-appb-img-000156
    Figure PCTKR2021095005-appb-img-000157
    Figure PCTKR2021095005-appb-img-000157
    Figure PCTKR2021095005-appb-img-000158
    Figure PCTKR2021095005-appb-img-000158
    Figure PCTKR2021095005-appb-img-000159
    Figure PCTKR2021095005-appb-img-000159
    Figure PCTKR2021095005-appb-img-000160
    Figure PCTKR2021095005-appb-img-000160
    Figure PCTKR2021095005-appb-img-000161
    Figure PCTKR2021095005-appb-img-000161
    Figure PCTKR2021095005-appb-img-000162
    Figure PCTKR2021095005-appb-img-000162
    Figure PCTKR2021095005-appb-img-000163
    Figure PCTKR2021095005-appb-img-000163
    Figure PCTKR2021095005-appb-img-000164
    .
    Figure PCTKR2021095005-appb-img-000164
    .
  11. 청구항 1에 있어서, 상기 화학식 2는 하기 화합물 중에서 선택되는 어느 하나인 것인 유기 발광 소자:The organic light emitting diode of claim 1, wherein Chemical Formula 2 is any one selected from the following compounds:
    Figure PCTKR2021095005-appb-img-000165
    Figure PCTKR2021095005-appb-img-000165
    Figure PCTKR2021095005-appb-img-000166
    Figure PCTKR2021095005-appb-img-000166
    Figure PCTKR2021095005-appb-img-000167
    Figure PCTKR2021095005-appb-img-000167
    Figure PCTKR2021095005-appb-img-000168
    Figure PCTKR2021095005-appb-img-000168
    Figure PCTKR2021095005-appb-img-000169
    Figure PCTKR2021095005-appb-img-000169
    Figure PCTKR2021095005-appb-img-000170
    Figure PCTKR2021095005-appb-img-000170
    Figure PCTKR2021095005-appb-img-000171
    Figure PCTKR2021095005-appb-img-000171
    Figure PCTKR2021095005-appb-img-000172
    Figure PCTKR2021095005-appb-img-000172
    Figure PCTKR2021095005-appb-img-000173
    Figure PCTKR2021095005-appb-img-000173
    Figure PCTKR2021095005-appb-img-000174
    Figure PCTKR2021095005-appb-img-000174
    Figure PCTKR2021095005-appb-img-000175
    Figure PCTKR2021095005-appb-img-000175
    Figure PCTKR2021095005-appb-img-000176
    Figure PCTKR2021095005-appb-img-000176
    Figure PCTKR2021095005-appb-img-000177
    Figure PCTKR2021095005-appb-img-000177
    Figure PCTKR2021095005-appb-img-000178
    Figure PCTKR2021095005-appb-img-000178
    Figure PCTKR2021095005-appb-img-000179
    Figure PCTKR2021095005-appb-img-000179
    Figure PCTKR2021095005-appb-img-000180
    Figure PCTKR2021095005-appb-img-000180
    Figure PCTKR2021095005-appb-img-000181
    Figure PCTKR2021095005-appb-img-000181
    Figure PCTKR2021095005-appb-img-000182
    Figure PCTKR2021095005-appb-img-000182
    Figure PCTKR2021095005-appb-img-000183
    Figure PCTKR2021095005-appb-img-000183
    Figure PCTKR2021095005-appb-img-000184
    Figure PCTKR2021095005-appb-img-000184
    Figure PCTKR2021095005-appb-img-000185
    Figure PCTKR2021095005-appb-img-000185
    Figure PCTKR2021095005-appb-img-000186
    Figure PCTKR2021095005-appb-img-000186
    Figure PCTKR2021095005-appb-img-000187
    Figure PCTKR2021095005-appb-img-000187
    Figure PCTKR2021095005-appb-img-000188
    Figure PCTKR2021095005-appb-img-000188
    Figure PCTKR2021095005-appb-img-000189
    Figure PCTKR2021095005-appb-img-000189
    Figure PCTKR2021095005-appb-img-000190
    Figure PCTKR2021095005-appb-img-000190
    Figure PCTKR2021095005-appb-img-000191
    Figure PCTKR2021095005-appb-img-000191
    Figure PCTKR2021095005-appb-img-000192
    Figure PCTKR2021095005-appb-img-000192
    Figure PCTKR2021095005-appb-img-000193
    Figure PCTKR2021095005-appb-img-000193
    Figure PCTKR2021095005-appb-img-000194
    Figure PCTKR2021095005-appb-img-000194
    Figure PCTKR2021095005-appb-img-000195
    Figure PCTKR2021095005-appb-img-000195
    Figure PCTKR2021095005-appb-img-000196
    .
    Figure PCTKR2021095005-appb-img-000196
    .
  12. 청구항 1에 있어서, 상기 유기물층 중 애노드에 접하는 유기물층은 카바졸계 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device according to claim 1, wherein the organic material layer in contact with the anode among the organic material layers includes a carbazole-based compound.
  13. 청구항 1에 있어서, 상기 유기물층은 정공수송층 및 정공조절층을 포함하고, 상기 정공수송층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting diode of claim 1, wherein the organic material layer includes a hole transport layer and a hole control layer, and the hole transport layer includes the compound represented by Formula 1 above.
  14. 청구항 1에 있어서, 상기 화학식 1의 삼중항 에너지는 2.4eV 내지 2.8eV인 것인 유기 발광 소자.The organic light emitting diode of claim 1, wherein the triplet energy of Formula 1 is 2.4 eV to 2.8 eV.
  15. 청구항 1에 있어서, 상기 발광층은 호스트 및 도펀트를 포함하고, 상기 호스트는 상기 화학식 2로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting diode of claim 1 , wherein the emission layer includes a host and a dopant, and the host includes the compound represented by Formula 2 above.
  16. 청구항 1에 있어서, 상기 발광층은 2 종 이상의 혼합 호스트를 포함하고, 상기 2 종 이상의 혼합 호스트 중 1종 이상은 상기 화학식 2로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 1 , wherein the light emitting layer includes two or more mixed hosts, and at least one of the two or more mixed hosts includes the compound represented by Formula 2 above.
  17. 청구항 1에 있어서, 상기 발광층은 2 종 이상의 혼합 호스트를 포함하고, 상기 2 종 이상의 혼합 호스트는 중 적어도 1종은 상기 화학식 2로 표시되는 화합물을 포함하고, 나머지는 중수소를 치환기로 포함하지 않는 안트라센계 화합물, 및 중수소를 치환기로 포함하고 상기 화학식 2와 상이한 안트라센계 화합물 중에서 선택되는 1 이상을 포함하는 것인 유기 발광 소자.The method according to claim 1, wherein the light emitting layer comprises two or more kinds of mixed hosts, at least one of the two or more kinds of mixed hosts includes the compound represented by Formula 2, and the remainder of the anthracene does not contain deuterium as a substituent. An organic light emitting device comprising at least one selected from anthracene-based compounds having deuterium as a substituent and different from Chemical Formula 2, and anthracene-based compounds.
  18. 청구항 1에 있어서, 상기 유기 발광 소자는 발광 스펙트럼의 최대 발광 파장(λ max)이 400 nm 내지 470 nm인 것인 유기 발광 소자.The organic light emitting device of claim 1, wherein the organic light emitting device has a maximum emission wavelength (λ max ) of an emission spectrum of 400 nm to 470 nm.
  19. 청구항 1에 있어서, 상기 발광층은 호스트 및 도펀트를 포함하고, 상기 도펀트는 형광 도펀트인 것인 유기 발광 소자.The organic light-emitting device of claim 1 , wherein the emission layer includes a host and a dopant, and the dopant is a fluorescent dopant.
  20. 청구항 1에 있어서, 상기 발광층은 호스트 및 도펀트를 포함하고, 상기 도펀트는 파이렌계 화합물 및 비파이렌계 화합물 중에서 선택되는 1 이상을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 1, wherein the emission layer includes a host and a dopant, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.
  21. 청구항 20에 있어서, 상기 비파이렌계 화합물은 보론계 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting diode of claim 20, wherein the non-pyrene-based compound includes a boron-based compound.
  22. 청구항 1에 있어서, 상기 유기 발광 소자는 상기 캐소드와 상기 발광층 사이에 구비된 전자수송영역을 포함하고, 상기 전자수송영역은 하기 화학식 3으로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The organic light emitting device according to claim 1, wherein the organic light emitting device includes an electron transport region provided between the cathode and the light emitting layer, and the electron transport region includes a compound represented by the following Chemical Formula 3:
    [화학식 3][Formula 3]
    Figure PCTKR2021095005-appb-img-000197
    Figure PCTKR2021095005-appb-img-000197
    상기 화학식 3에 있어서,In Formula 3,
    X1은 N 또는 Q101이고, X2는 N 또는 Q102이고, X3는 N 또는 Q103이며, X1 is N or Q101, X2 is N or Q102, X3 is N or Q103,
    상기 X1 내지 X3 중 적어도 하나는 N이고,At least one of X1 to X3 is N,
    Q101 내지 Q103 및 Q1 내지 Q3는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 히드록시기; 시아노기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Q101 to Q103 and Q1 to Q3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; cyano group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  23. 청구항 22에 있어서, 상기 전자수송영역은 상기 화학식 3으로 표시되는 화합물, 유기 알칼리금속 착화합물, 및 이들의 혼합물을 포함하는 것인 유기 발광 소자.The organic light emitting diode of claim 22 , wherein the electron transport region includes a compound represented by Formula 3, an organic alkali metal complex, and a mixture thereof.
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WO2018164265A1 (en) * 2017-03-10 2018-09-13 出光興産株式会社 Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device
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WO2022230972A1 (en) * 2021-04-28 2022-11-03 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic appliance
EP4212535A4 (en) * 2021-09-01 2024-05-22 Lg Chemical Ltd Compound and organic light-emitting element comprising same
CN115745932A (en) * 2021-09-03 2023-03-07 三星Sdi株式会社 Compound for organic photoelectric device, organic photoelectric device and display device
WO2024034916A1 (en) * 2022-08-08 2024-02-15 주식회사 엘지화학 Organic light-emitting element
KR20240046006A (en) 2022-09-30 2024-04-08 이데미쓰 고산 가부시키가이샤 Organic electroluminescent element and electronic device

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KR102655910B1 (en) 2024-04-09
KR20210093788A (en) 2021-07-28

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