WO2021150090A1 - 유기 발광 소자 - Google Patents

유기 발광 소자 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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English (en)
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/zh
Publication of WO2021150090A1 publication Critical patent/WO2021150090A1/ko

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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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KR20240046006A (ko) 2022-09-30 2024-04-08 이데미쓰 고산 가부시키가이샤 유기 전기발광 소자 및 전자 기기
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