CN113950754B - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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CN113950754B
CN113950754B CN202180003753.6A CN202180003753A CN113950754B CN 113950754 B CN113950754 B CN 113950754B CN 202180003753 A CN202180003753 A CN 202180003753A CN 113950754 B CN113950754 B CN 113950754B
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CN113950754A (en
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河宰承
洪玩杓
李豪中
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LG Chem Ltd
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Abstract

The present specification relates to an organic light emitting device, including: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; and a hole transport region provided between the light emitting layer and the anode and including at least 2 organic layers, wherein the organic layer in contact with the light emitting layer includes a compound of chemical formula 1, and the light emitting layer includes a compound of chemical formula 2.

Description

Organic light emitting device
Technical Field
The present application claims priority from korean patent application No. 10-2020-0007105, filed to the korean patent office on 1 month and 20 days 2020, the entire contents of which are included in the present specification.
The present specification relates to organic light emitting devices.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exciton) are formed, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides an organic light emitting device.
Solution to the problem
An embodiment of the present specification provides an organic light emitting device, including: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; and a hole transport region provided between the light-emitting layer and the anode and including at least 2 organic layers, wherein the organic layer in contact with the light-emitting layer includes a compound represented by the following chemical formula 1, and the light-emitting layer includes a compound represented by the following chemical formula 2.
[ Chemical formula 1]
In the above-mentioned chemical formula 1,
Any one of R8 and R9 is a group represented by the following formula a, a group other than the group represented by the following formula a in the above R8 and R9, R1 to R7 and R10 to R18 are the same or different from each other, each is independently hydrogen, deuterium, 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, or a group other than the group represented by the following formula a in the above R8 and R9, R1 to R6, R7, and an adjacent group in R10 to R18 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring,
[ Chemical formula a ]
In the above-mentioned chemical formula a,
L1 to L3 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
Ar1 and Ar2 are the same or different from each other and are each independently deuterium, a halogen group, a hydroxyl group, a cyano group, a 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 to l3 are each an integer of 1 to 3,
When L1 is 2 or more, the 2 or more L1 s are the same or different from each other,
When L2 is 2 or more, the 2 or more L2 s are the same or different from each other,
When L3 is 2 or more, the 2 or more L3 s are the same or different from each other,
Represents a site to which R8 or R9 of the above chemical formula 1 is bonded,
[ Chemical formula 2]
In the above-mentioned chemical formula 2,
At least one of G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a 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,
[ Chemical formula b ]
In the above-mentioned chemical formula b,
A and B are the same or different from each other and are a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
L4 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
L4 is an integer of 1 to 3,
When L4 is 2 or more, the 2 or more L4 s are the same or different from each other,
Represents a site to which at least one of G1 to G10 of the above chemical formula 2 is bonded,
The deuterium substitution rate of the above chemical formula 2 is 40% to 100%.
Effects of the invention
The organic light emitting device according to an embodiment of the present disclosure includes the compound of chemical formula 1 in an organic layer in contact with a light emitting layer, and includes the compound of chemical formula 2 in a light emitting layer, so that the driving voltage is low, the light efficiency is improved, and the life characteristics of the device can be improved by using the thermal stability of the compound.
Drawings
Fig. 1 to 4 illustrate examples of an organic light emitting device according to an embodiment of the present specification.
FIG. 5 is a diagram showing an MS chart of Compound A.
[ Description of the symbols ]
1: Substrate board
2: Anode
3: Hole transport region
4: Light-emitting layer
5: Cathode electrode
3-1: Hole transport layer
3-2: Hole regulating layer
6: Hole injection layer
7: Electron transport region
7-1: Electronic regulating layer
7-2: Electron transport layer
8: Electron injection layer
Detailed Description
The present specification will be described in more detail below.
In the present specification, "deuterated" or "deuterated" means that hydrogen at a position of a compound which can be substituted is substituted with deuterium.
In the present specification, "deuterated" refers to a compound or group in which all hydrogen in the molecule is substituted with deuterium, and has the same meaning as "100% deuterated".
In the present specification, "X% deuterated", "deuterated degree X%", or "deuterium substitution rate X%" means that X% of hydrogen at a position that can be substituted in the structure is substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" means that 2 of 8 hydrogens at the position where the dibenzofuran can be substituted are substituted with deuterium, the "deuteration degree of the dibenzofuran is 25%, or the" deuterium substitution rate of the dibenzofuran is 25%.
In the present specification, the "degree of deuteration" or "deuterium substitution rate" can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1 H NMR), TLC/MS (Thin layer chromatography/mass spectrometry, thin-Layer Chromatography/Mass Spectrometry), or GC/MS (gas chromatography/mass spectrometry ).
Specifically, in the analysis of "deuteration degree" or "deuterium substitution rate" by nuclear magnetic resonance spectroscopy (1 H NMR), DMF (dimethylformamide) may be added as an internal standard (INTERNAL STANDARD), and the deuteration degree or deuterium substitution rate may be calculated from the integral ratio of the total peak (peak) by the integral (integration) ratio on 1 H NMR.
In addition, when "deuteration degree" or "deuterium substitution rate" is analyzed by TLC/MS (thin layer chromatography/mass spectrometry), the substitution rate can be calculated based on the maximum value (intermediate value) of the distribution of molecular weight formation at the end of the reaction. For example, when the molecular weight of the following starting material is 506 in analyzing the deuteration degree of the following compound a, and when it is indicated that the maximum value (intermediate value) of the molecular weight of the following compound a in the MS chart of fig. 5 is 527, 21 out of hydrogens (26) at the position where the following starting material can be substituted are substituted with deuterium, and thus it can be calculated that about 81% of the hydrogens are deuterated.
In the present specification, D means deuterium.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present specification, the term "layer" is used interchangeably with "film" mainly used in the art, and means a coating layer covering a target region. The size of the "layers" is not limited, and the respective "layers" may be the same or different in size. According to an embodiment, the size of the "layer" may be equal to the size of the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel (sub-pixel).
In the present specification, the inclusion of a specific a substance in the B layer means that i) a case where 1 or more a substances are included in the B layer of one layer, and ii) a case where the B layer is composed of 1 or more layers and a substances are included in 1 or more layers in the B layer of the plurality of layers are all included.
In the present specification, the inclusion of a specific substance a in the C layer or the D layer means that all cases where i) is included in 1 layer or more of the C layers of 1 layer or more, or ii) is included in 1 layer or more of the D layers of 1 layer or more, or iii) is included in the C layers of 1 layer or more and the D layers of 1 layer or more, respectively, are included.
In this specification, "or/and" refers to "or/and" including but not exclusive of. For example, the condition a or B satisfies any one of the following: a is true (or present), B is false (or absent); a is false (or absent), B is true (or present); both A and B are true (or present).
In the present specification, "a mixture of these" or "mixing" means that the mixture contains 2 or more substances. The above-mentioned "mixture" or "mixing" may include a state of uniform and/or non-uniform mixing, a dissolved state, a state of uniform and/or non-uniform dispersion, etc., but is not limited thereto.
In the present specification, unless defined otherwise, all technical and scientific terms used in the present specification have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar or equivalent to those described in this specification can be used in the practice or testing of embodiments of the present invention, but with the appropriate methods and materials described below. All publications, patent applications, patents, and other references mentioned in this specification are herein incorporated by reference in their entirety and, in the event of a conflict, the specification, including definitions, to the exclusion of any specific language (passage). In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.
In the present specification, examples of substituents are described below, but are not limited thereto.
In the present description of the invention,Indicating the location of the connection.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or more substituents selected from deuterium, halogen group, hydroxyl group, cyano group, nitro group, alkyl group, cycloalkyl group, alkoxy group, alkenyl group, haloalkyl group, silyl group, boron group, amine group, aryl group and heteroaryl group, or substituted with a substituent in which 2 or more substituents among the above exemplified substituents are linked, or does not have any substituent.
In the present specification, the connection of 2 or more substituents means that hydrogen of any substituent is connected to other substituents. For example, 2 substituents are linked to a phenyl group and a naphthyl group and may beSuch substituents. Further, 3 substituent linkages include not only (substituent 1) - (substituent 2) - (substituent 3) linked continuously, but also (substituent 2) and (substituent 3) linked in (substituent 1). For example, phenyl, naphthyl and isopropyl groups may be linked to become/>Such substituents. The same definition as above applies also for the case where 4 or more substituents are linked.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof 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-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 30 carbon atoms is preferable, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like are included, but the present invention is not limited thereto.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the above haloalkyl group means hydrogen substituted with at least one halogen group instead of an alkyl group in the definition of the above alkyl group.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be a single ring or a multiple ring.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. Preferably having 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, the above fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the case where the above fluorenyl group is substituted, there areAnd the like, but is not limited thereto.
In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted by the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In this specification, a heteroaryl group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl,/>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo/>Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthridinyl (PHENANTHRIDINE), phenanthroline (phenanthrine), iso/>Azolyl, thiadiazolyl, dibenzofuranyl, dibenzosilol, and pheno/>Thioyl (phenoxathiine), pheno/>Oxazinyl (phenoxazine), phenothiazinyl (phenothiazine), indanocarbazolyl, spirofluorenoxanthenyl, spirofluorenothioyl, and the like, but are not limited thereto.
In the present specification, the silyl group may be an alkylsilyl group, arylsilyl group, heteroarylsilyl group or the like. The alkyl group in the alkylsilyl group may be exemplified by the alkyl group, the aryl group in the arylsilyl group may be exemplified by the aryl group, and the heteroaryl group in the heteroarylsilyl group may be exemplified by the heteroaryl group.
In this specification, the boron group may be-BR 100R101, and the above-mentioned R 100 and R 101 are the same or different and may each be independently selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
In the present specification, the amine group may be selected from the group consisting of-NH 2, alkylamino, N-alkylaryl amine, arylamino, N-arylheteroaryl amine, N-alkylheteroaryl amine and heteroaryl amine, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamine group, naphthylamino group, biphenylamino group, anthracenyl amino group, 9-methyl-anthracenyl amino group, diphenylamino group, xylylamino group, N-phenyltolylamino group, triphenylamino group, N-phenylbiphenylamino group, N-phenylnaphthylamino group, N-biphenylnaphthylamino group, N-naphthylfluorenylamino group, N-phenylphenanthrylamino group, N-biphenylphenanthrenylamino group, N-phenylfluorenylamino group, N-phenylterphenylamino group, N-phenanthrenylfluorenylamino group, N-biphenylfluorenylamino group and the like, but are not limited thereto.
In the present specification, the N-alkylaryl amine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine group. The alkyl group and the aryl group in the above-mentioned N-alkylaryl amine group are the same as exemplified for the alkyl group and the aryl group described above.
In the present specification, an N-arylheteroarylamino group means an amino group substituted with an aryl group and a heteroaryl group on N of the amino group. The aryl and heteroaryl groups in the above-described N-arylheteroarylamine groups are the same as the above-described examples of aryl and heteroaryl groups.
In the present specification, an N-alkylheteroaryl amine group means an amine group substituted with an alkyl group and a heteroaryl group on the N of the amine group. The alkyl and heteroaryl groups in the above-mentioned N-alkylheteroaryl amine groups are the same as the examples of the alkyl and heteroaryl groups described above.
In the present specification, as examples of the alkylamino group, there are a substituted or unsubstituted monoalkylamino group, or a substituted or unsubstituted dialkylamino group. The alkyl group in the above-mentioned alkylamino group may be a linear or branched alkyl group. The alkylamino group containing 2 or more of the above-mentioned alkyl groups may contain a linear alkyl group, a branched alkyl group, or may contain both a linear alkyl group and a branched alkyl group. For example, the alkyl group in the above-mentioned alkylamino group may be selected from the examples of the alkyl group described above.
In the present specification, as examples of the arylamine group, there are substituted or unsubstituted monoarylamine groups, or substituted or unsubstituted diarylamino groups. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more of the above aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
In the present specification, as examples of the heteroarylamino group, there is a substituted or unsubstituted mono-heteroarylamino group or a substituted or unsubstituted di-heteroarylamino group. The heteroarylamine group containing 2 or more of the above heteroaryl groups may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or may contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the above heteroaryl amine group may be selected from the examples of heteroaryl groups described above.
In the present specification, "adjacent 2 groups are bonded to each other to form a ring" in a substituent means that adjacent groups are bonded to each other to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
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 ring and an aliphatic hydrocarbon ring, and may be selected from the examples of cycloalkyl groups and aryl groups, except for the above 1-valent groups.
In this specification, a heterocyclic ring contains 1 or more heteroatoms which are non-carbon atoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se and S and the like. The heterocycle may be a single ring or a multiple ring, may be an aromatic, aliphatic, or an aromatic and aliphatic condensed ring, and the aromatic heterocycle may be selected from the examples of the heteroaryl group, except that it is not 1 valent.
In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more hetero atoms. Examples of aliphatic heterocycles include ethylene oxide (oxalane), tetrahydrofuran, and 1, 4-di-Alkane (1, 4-dioxane), pyrrolidine, piperidine, morpholine (morpholine), oxepane, azacyclooctane, thiacyclooctane, and the like, but is not limited thereto.
In the present specification, arylene means a group having two bonding positions on an aryl group, i.e., a 2-valent group. These are not limited to the 2-valent groups, and the above description of the aryl groups may be applied.
In the present specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. They may be suitable for the above description of heteroaryl groups, except that each is a 2-valent group.
An organic light emitting device according to an embodiment of the present specification includes: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; and a hole transport region provided between the light-emitting layer and the anode and including at least 2 organic layers, wherein the organic layer in contact with the light-emitting layer includes a compound represented by the following chemical formula 1, and the light-emitting layer includes a compound represented by the following chemical formula 2. At this time, the deuterium substitution rate of the compound of the above chemical formula 2 is 40% to 100%.
The organic light emitting device according to the above embodiment is characterized in that the compound of chemical formula 1 is contained between the anode and the light emitting layer, that is, in the hole transporting region, and the compound of chemical formula 2 is contained in the light emitting layer. By including the compound of chemical formula 1 in the hole transporting region of the organic light emitting device, injection and transport of holes are accelerated, transport of carriers into the light emitting layer is maximized, efficiency of the light emitting layer can be improved, and by including the compound of chemical formula 2 in the light emitting layer, a device having excellent lifetime can be obtained.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 40% to 100%, preferably 40% to 99%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 45% to 100%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 50% to 100%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 65% to 100%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 70% to 100%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 80% to 100%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 90% to 100%.
According to one embodiment of the present specification, the deuterium substitution rate of the above chemical formula 2 is 100%.
The deuterium substitution rate can be calculated by the method described above. According to an additional example, at least one deuterium is directly substituted on the anthracene of the above chemical formula 2. The light-emitting layer of the organic light-emitting device is a light-emitting region, and is a region where loss of molecules due to energy is large. Since the carbon-deuterium bond is stronger than the carbon-hydrogen bond, deuterium has a higher mass value than hydrogen, and zero energy (Zero point energy) with carbon is reduced, the bond energy is high, and therefore, the carbon-hydrogen bond contained in the molecule of the compound of chemical formula 2 is replaced with the carbon-deuterium bond to increase the bond energy of the molecule, and a device having an excellent lifetime can be obtained.
An organic light emitting device including the compound of chemical formula 2 having a deuterium substitution rate according to an embodiment of the present specification has an effect of improving lifetime.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 0% to 100%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 0.01% to 100%.
According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 1% to 100%.
According to an embodiment of the present specification, at least one of hydrogens of the position capable of being substituted of the above chemical formula 1 is substituted with deuterium.
According to an embodiment of the present specification, any one of the R8 and R9 is a group represented by the above formula a, a group other than the group represented by the above formula a in the R8 and R9, R1 to R7, and R10 to R18 are the same or different from each other, each is independently hydrogen, deuterium, 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, or a group other than the group represented by the below formula a in the R8 and R9, R1 to R6, R7, and an adjacent group in the R10 to R18 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
According to an embodiment of the present specification, the groups of R8 and R9 other than the group represented by the following chemical formula a, R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
According to an embodiment of the present specification, the groups of R8 and R9 other than the group represented by the following chemical formula a, R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.
According to an embodiment of the present specification, the groups of R8 and R9 other than the group represented by the following chemical formula a, R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted benzene ring.
According to an embodiment of the present specification, the groups other than the group represented by the following chemical formula a, R1 to R6, R7, and R10 to R18 in the above-described R8 and R9 are bonded to each other to form a benzene ring.
According to one embodiment of the present specification, R1 and R18 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
According to an 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.
According to an embodiment of the present specification, the above R1 and R18 are combined with each other to form a substituted or unsubstituted fluorene ring.
According to one embodiment of the present specification, R1 and R18 are bonded to each other to form an aromatic hydrocarbon ring.
According to one 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.
According to an embodiment of the present specification, R1 and R18 are bonded to each other to form a fluorene ring.
According to an embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.
[ Chemical formula 1-1]
[ Chemical formulas 1-2]
[ Chemical formulas 1-3]
[ Chemical formulas 1-4]
In the above chemical formulas 1-1 to 1-4,
R2 to R17, R101 and R118 are identical to or different from each other and are each independently hydrogen, deuterium, 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,
The definitions of L1 to L3, ar1 and Ar2 are the same as those in the above chemical formula a.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18 in the above R8 and R9 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18 in the above R8 and R9 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18 in the above R8 and R9 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18 in the above R8 and R9 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18 in the above R8 and R9 are the same or different from each other, and each is independently hydrogen, deuterium, alkyl, or aryl substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a in the above-mentioned R8 and R9, R1 to R7 and R10 to R18 are the same or different from each other, and are each independently hydrogen, deuterium, 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, which is substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a in the above-mentioned R8 and R9, R1 to R7 and R10 to R18 are the same or different from each other, and are each independently hydrogen, deuterium, 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, which is substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a in the above-mentioned R8 and R9, R1 to R7 and R10 to R18 are the same or different from each other, and are each independently hydrogen, deuterium, 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, which is substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18 in the above R8 and R9 are the same or different from each other, and are each independently hydrogen, deuterium, tert-butyl, or phenyl substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, among the above-mentioned R8 and R9, a group other than the group represented by the following chemical formula a, R1 to R7, R11, and R13 to R18 are hydrogen.
According to an embodiment of the present specification, R12 is hydrogen, tert-butyl or phenyl.
According to an embodiment of the present specification, among the above-mentioned R8 and R9, a group other than the group represented by the following chemical formula a, R1 to R6, and R12 to R18 are hydrogen.
According to an embodiment of the present specification, R7 is phenyl substituted with deuterium.
According to one embodiment of the present specification, l1 is 1.
According to one embodiment of the present specification, l1 is 2.
According to one embodiment of the present specification, l2 is 1.
According to one embodiment of the present specification, l3 is 1.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and are each independently a directly bonded, 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.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and are each independently a directly bonded, 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.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, each independently being a direct bond; arylene substituted or unsubstituted with 1 or more selected from deuterium, alkyl, and aryl; or heteroarylene substituted or unsubstituted with deuterium or alkyl.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, each independently being a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is substituted or unsubstituted with 1 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 substituted or unsubstituted with deuterium, or a linear or branched alkyl group having 1 to 30 carbon atoms.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, each independently being a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, which is substituted or unsubstituted with 1 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, which is substituted or unsubstituted with deuterium, or a linear or branched alkyl group having 1 to 20 carbon atoms.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, each independently being a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a terphenylene group substituted or unsubstituted with deuterium; a 2-valent fluorenyl group substituted with 1 or more groups 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 2-valent benzofuranyl group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, each independently being a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a terphenylene group substituted or unsubstituted with deuterium; a 2-valent fluorenyl group substituted with 1 or more selected from deuterium, methyl, and phenyl groups; or a 2-valent benzofuranyl group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the above L1 to L3 are the same or different from each other, and each is independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group, a terphenylene group, a fluorenyl group of 2 valences substituted with 1 or more selected from a methyl group and a phenyl group, or a benzofuranyl group of 2 valences.
According to an embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
According to an embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms directly bonded, substituted or unsubstituted, or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms substituted or unsubstituted.
According to an embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms directly bonded, substituted or unsubstituted, or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms substituted or unsubstituted.
According to an embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms directly bonded, substituted or unsubstituted, or a monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms substituted or unsubstituted.
According to one embodiment of the present disclosure, L1 is a direct bond, a deuterium-substituted or unsubstituted arylene, or heteroarylene group.
According to an embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms, which is directly bonded, substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms, which is directly bonded, substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms, or a monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms, which is directly bonded, substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, L1 is a direct bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group substituted or unsubstituted with deuterium, or a benzofuranyl group having a valence of 2.
According to an embodiment of the present specification, L1 is a directly bonded, deuterium-substituted or unsubstituted phenylene, biphenylene, or 2-valent benzofuranyl group.
According to an embodiment of the present specification, the above-mentioned L2 and L3 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is directly bonded, or substituted or unsubstituted.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, and each is independently a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, which is directly bonded, or substituted or unsubstituted.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, each independently being a direct bond; or an arylene group substituted or unsubstituted with 1 or more members selected from deuterium, alkyl, and aryl.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, each independently being a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 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.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, each independently being a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 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.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, each independently being a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a terphenylene group substituted or unsubstituted with deuterium; or a 2-valent fluorenyl group substituted with 1 or more groups 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.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, each independently being a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a terphenylene group substituted or unsubstituted with deuterium; or a 2-valent fluorenyl group substituted with 1 or more selected from deuterium, methyl, and phenyl.
According to an embodiment of the present specification, the above L2 and L3 are the same or different from each other, and each is independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group, a terphenylene group, or a 2-valent fluorenyl group substituted with 1 or more selected from a methyl group and a phenyl group.
According to an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
According to an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is 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.
According to an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with 1 or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium, 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 a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 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.
According to an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with 1 or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium, and a linear or branched alkylsilyl group having 1 to 30 carbon atoms; biphenyl groups substituted or unsubstituted with 1 or more groups selected from deuterium, and linear or branched alkyl groups having 1 to 30 carbon atoms; a terphenyl group; a tetrabiphenyl group; a naphthyl group substituted or unsubstituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; triphenylene; a fluorenyl group substituted with 1 or more groups selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; carbazolyl; dibenzofuranyl; benzofuranyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or dibenzothienyl.
According to an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, each independently is a phenyl group substituted or unsubstituted with 1 or more selected from deuterium, t-butyl, trimethylsilyl, methyl, and phenyl; biphenyl substituted or unsubstituted with 1 or more selected from deuterium and tert-butyl; a terphenyl group; a tetrabiphenyl group; a naphthyl group substituted or unsubstituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; triphenylene; fluorenyl substituted with 1 or more selected from deuterium, tridentate methyl, and phenyl; carbazolyl; dibenzofuranyl; benzofuranyl substituted or unsubstituted with phenyl; or dibenzothienyl.
According to an embodiment of the present disclosure, R101 and R118 are hydrogen.
According to an embodiment of the present specification, at least one of the above-mentioned G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other, each being independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, at least one of the above-mentioned G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other, each being independently hydrogen, deuterium, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
According to an embodiment of the present specification, at least one of the above-mentioned G1 to G10 is a group represented by the following chemical formula b, and the others are the same as or different from each other, each being independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, at least one of the above-mentioned G1 to G10 is a group represented by the following chemical formula b, and the others are the same as or different from each other, each being independently hydrogen; deuterium; phenyl substituted or unsubstituted with 1 or more of aryl groups selected from deuterium, and monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; 1 or more substituted or unsubstituted naphthyl groups selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; 1 or more substituted or unsubstituted biphenyl groups selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; a terphenyl group substituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; triphenylene substituted or unsubstituted with deuterium; or pyrenyl substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, at least one of the above-mentioned G1 to G10 is a group represented by the following chemical formula b, and the others are the same as or different from each other, each being independently hydrogen; deuterium; phenyl substituted or unsubstituted with 1 or more selected from deuterium, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, and naphthyl substituted or unsubstituted with deuterium; 1 or more substituted or unsubstituted naphthyl groups selected from deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium; biphenyl groups substituted or unsubstituted with 1 or more selected from deuterium, and phenyl groups substituted or unsubstituted with deuterium; a terphenyl group substituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; triphenylene substituted or unsubstituted with deuterium; or pyrenyl substituted or unsubstituted with deuterium.
According to one embodiment of the present specification, G1 is a group represented by the formula b.
According to an embodiment of the present specification, G3 is a group represented by the formula b.
According to an embodiment of the present specification, the above-mentioned G1 and G6 are the same or different from each other, each being a group represented by the above-mentioned chemical formula b.
According to one embodiment of the present specification, l4 is 1.
According to one embodiment of the present specification, L4 is a direct bond, or a substituted or unsubstituted arylene group.
According to an embodiment of the present specification, L4 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is directly bonded, or substituted or unsubstituted.
According to an embodiment of the present specification, L4 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, which is directly bonded, or substituted or unsubstituted.
According to one embodiment of the present specification, L4 is a direct bond, or a substituted or unsubstituted arylene group.
According to an embodiment of the present specification, L4 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, L4 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, which is directly bonded, or substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the L4 is a direct bond, a phenylene group substituted or unsubstituted with deuterium, or a naphthylene group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, a and B are the same or different from each other, and each is independently a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
According to an embodiment of the present specification, a and B are the same or different from each other, and each is 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 heterocyclic ring having 2 to 30 carbon atoms.
According to an embodiment of the present specification, a and B are the same or different from each other, and each is independently a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with 1 or more of monocyclic or polycyclic aromatic groups having 6 to 30 carbon atoms, which are selected from deuterium, and which are substituted or unsubstituted with deuterium; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the above a and B are the same or different from each other, each independently is 1 or more substituted or unsubstituted benzene rings selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by deuterium; a naphthalene ring substituted or unsubstituted with deuterium; a phenanthrene ring substituted or unsubstituted with deuterium; a triphenylene ring substituted or unsubstituted with deuterium; or a dibenzofuran ring substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the above a and B are the same or different from each other, each independently is a benzene ring substituted or unsubstituted with 1 or more selected from 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 naphthalene ring substituted or unsubstituted with deuterium; a phenanthrene ring substituted or unsubstituted with deuterium; a triphenylene ring substituted or unsubstituted with deuterium; or a dibenzofuran ring substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.
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According to an embodiment of the present specification, the chemical formula 2 is any one selected from the following compounds.
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According to an embodiment of the present specification, the compounds of the above chemical formulas 1 and 2 may be manufactured using starting materials and reaction conditions known in the art. The type and number of substituents may be determined by appropriately selecting known starting materials by those skilled in the art. Further, the compounds of the above chemical formulas 1 and 2 can be obtained from commercially available compounds.
According to an embodiment of the present disclosure, the organic layer connected to the anode includes a carbazole-based compound.
According to an embodiment of the present specification, the carbazole-based compound may be represented by the following structural formula, but is not limited thereto.
In the above-mentioned structural formula, the water-soluble polymer,
T1 to T3 are identical to or different from one another and are each independently of one another deuterium, halogen radicals, hydroxy, cyano, nitro, alkyl, cycloalkyl, alkoxy, alkenyl, haloalkyl, silyl, boryl, amino, aryl or heteroaryl, or adjacent radicals can be combined with one another to form a substituted or unsubstituted ring,
T1 is an integer of 1 to 4, and when T1 is 2 or more, 2 or more of T1 s are the same or different from each other,
T2 is an integer of 1 to 4, and when T2 is 2 or more, 2 or more of T2 are the same or different from each other,
T3 is an integer of 1 to 10, and when T3 is 2 or more, 2 or more T3 s are the same or different from each other.
According to an embodiment of the present specification, the carbazole-based compound may be selected from the following compounds, but is not limited thereto.
According to an embodiment of the present specification, the organic layer includes a hole transporting layer and a hole adjusting layer, and the hole transporting layer includes a compound represented by chemical formula 1.
According to an embodiment of the present specification, the organic layer includes a hole transporting layer and a hole adjusting layer, and the hole adjusting layer includes a compound represented by chemical formula 1.
The hole-adjusting layer according to an embodiment of the present specification includes a compound represented by chemical formula 1 above, and the deuterium substitution rate of chemical formula 1 above is 1% to 100%.
According to an embodiment of the present disclosure, a hole transport region is provided between the anode and the light-emitting layer, the hole transport region includes the hole transport layer and a hole adjustment layer, and the hole transport layer is provided in contact with the hole adjustment layer.
According to an embodiment of the present disclosure, the hole adjusting layer is provided in contact with the light emitting layer.
According to an embodiment of the present specification, a hole injection layer may be included between the anode and the hole transport layer.
For example, the structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 to 4, but is not limited thereto.
Fig. 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. Fig. 1 above is an exemplary structure according to an embodiment of the present disclosure, and may further include other organic layers.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole-transporting region 3 including a hole-transporting layer 3-1 and a hole-adjusting layer 3-2, a light-emitting layer 4, and a cathode 5 are sequentially stacked on a substrate 1. Fig. 2 above is an exemplary structure according to an embodiment of the present disclosure, and may further include other organic layers.
Fig. 3 illustrates a structure of an organic light-emitting device in which 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 are sequentially stacked on a substrate 1. Fig. 3 above is an exemplary structure according to an embodiment of the present disclosure, and may further include other organic layers.
Fig. 4 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 6, a hole transport region 3 including a hole transport layer 3-1 and a hole adjustment layer 3-2, a light emitting layer 4, an electron transport region 7 including an electron adjustment layer 7-1 and an electron transport layer 7-2, an electron injection layer 8, and a cathode 5 are sequentially stacked on a substrate 1. Fig. 4 above is an exemplary structure according to an embodiment of the present disclosure, and may further include other organic layers.
According to an embodiment of the present disclosure, the hole transport layer has a thickness of 50nm to 200nm.
According to an embodiment of the present disclosure, the thickness of the hole adjusting layer is 10nm to 150nm.
The hole transport region is formed of a plurality or singular of layers including a hole transport layer and a hole adjustment layer, and the thickness of the hole transport region may be determined based on an optimum point within the thickness in order to optimize the optical characteristics of the organic light emitting device.
According to an embodiment of the present specification, the triplet energy of chemical formula 1 is 2.4eV to 2.8eV.
When the layer in the hole transport region connected to the light emitting layer, that is, the layer including the above chemical formula 1 has the above triplet energy range, the layer according to an embodiment of the present specification generally exhibits relatively high singlet energy and thus generally has low highest occupied orbital energy. Therefore, carrier and exciton migration or transition in the light emitting layer are not easy, and thus the efficiency of the fabricated organic light emitting device can be improved, and stability can be brought.
In the present specification, "energy level" refers to the amount of energy. Therefore, the energy level is interpreted as an absolute value representing the energy value. For example, a low or deep energy level refers to an increase in absolute value from the vacuum level to the negative direction.
In this specification, HOMO (highest occupied molecular orbital ) refers to a molecular orbital function (highest occupied molecular orbital) in which electrons are located in the highest energy region among regions that can participate in binding, LUMO (lowest unoccupied molecular orbital ) refers to a molecular orbital function (lowest unoccupied molecular orbital) in which electrons are located in the lowest energy region among the anti-bonding regions, and HOMO energy level refers to a distance from a vacuum energy level to the HOMO. Further, LUMO level refers to the distance from vacuum level to LUMO. In order to grasp the electron distribution in the molecule and grasp the optical properties, a specific structure is required. In addition, the electronic structure has a structure that is different in each of neutral, anionic, and cationic states depending on the charge state of the molecule. For driving the device, energy levels in the neutral state, the cationic state, and the anionic state are all important, but as a representative, HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) in the neutral state are considered to be important physical properties. To determine the molecular structure of a chemical, the input structure is optimized using the density functional method (density functional theory). For DFT calculation, BPW91 algorithm (beck exchange function and Perdew correlation function), beck exchange AND PERDEW correlation-correlation functional) and DNP (binary basis set of polarization functions, double numerical basis set including polarization functional) basis set (basis set) were used. The BPW91 algorithm is disclosed in papers "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 is disclosed in papers "B.Delley, J.Chem.Phys.,92,508 (1990)".
For the calculation with the density functional method, a package "DMol3" from Biovia company (package) may be used. When the optimal molecular structure is determined by the method given above, the electron-occupiable energy level can be obtained as a result.
In the present specification, triplet energy refers to an electron state in which the number of spin quanta in a molecule is 1. In order to obtain physical properties of the excited state of the optimal molecular structure determined by the above method, the triplet energy is calculated as energy levels of the singlet state and the triplet state by using the time-density functional method (TIME DEPENDENT DENSITY functional theory: TD-DFT). The density functional calculation may be performed using the commercial calculation program "Gaussian09" package developed by Gaussian (Gaussian) corporation. For time-density functional calculation, the B3PW91 algorithm (beck exchange function and Perdew correlation function) and the 6-31G basis set were used. The 6-31G basic set is disclosed in the paper "j.a.pople et al, j.chem.Phys.56,2257 (1972)". For the optimal molecular structure determined using the density functional method, the energy that the electrons have when arranged in a single state (single) and a triplet state (triplet) is calculated using the time-dependent density functional method (TD-DFT).
According to an embodiment of the present disclosure, the light emitting layer includes a host and a dopant.
According to an embodiment of the present specification, the host includes the compound represented by chemical formula 2 and the dopant.
According to an embodiment of the present disclosure, the dopant is a blue dopant.
According to an embodiment of the present disclosure, the organic light emitting device is a blue organic light emitting device.
According to an embodiment of the present specification, the light emitting layer includes 2 or more mixed hosts, and 1 or more of the 2 or more mixed hosts include the compound represented by chemical formula 2.
According to one embodiment of the present disclosure, the light-emitting layer includes 2 or more mixed hosts, at least 1 of the 2 or more mixed hosts includes the compound represented by chemical formula 2, and the remaining anthracene-based compounds including no deuterium as a substituent.
According to one embodiment of the present disclosure, the light-emitting layer includes 2 or more mixed hosts, at least 1 of the 2 or more mixed hosts includes the compound represented by chemical formula 2, and the remaining includes an anthracene-based compound including deuterium as a substituent and different from the chemical formula 2.
According to an embodiment of the present disclosure, the light-emitting layer includes 2 or more mixed hosts, at least 1 of the 2 or more mixed hosts includes the compound represented by the chemical formula 2, and the remaining includes 1 or more selected from an anthracene compound including no deuterium as a substituent and an anthracene compound including deuterium as a substituent and different from the chemical formula 2.
At least 1 of the above 2 or more mixed hosts contains the compound represented by the above chemical formula 2, and the anthracene-based host used in the art can be used without limitation as long as it is different from the above chemical formula 2, and is not limited thereto.
The organic light emitting device using 2 or more kinds of hybrid hosts according to an embodiment of the present specification mixes advantages of the respective hosts to improve device performance, for example, 1 kind of host having high efficiency and low voltage effects and 1 kind of host having long life effects are mixed when 2 kinds of hosts are mixed, so that the organic light emitting device having high efficiency, low voltage and long life effects can be manufactured.
According to an embodiment of the present specification, the maximum emission wavelength (λ Maximum value ) of the emission spectrum of the above-mentioned organic light-emitting device is 400nm to 470nm.
According to an embodiment of the present disclosure, the light emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant.
According to one embodiment of the present disclosure, the light-emitting layer includes a host and a dopant, and the dopant includes 1 or more selected from pyrene compounds and non-pyrene compounds.
The pyrene compound and the non-pyrene compound may be used without limitation as long as they are used in the art, but are not limited thereto.
According to one embodiment of the present disclosure, the non-pyrene compound includes a boron compound.
According to one embodiment of the present disclosure, the light emitting layer includes a host including the compound represented by chemical formula 2 and a dopant including 1 or more selected from pyrene compounds and non-pyrene compounds.
According to an embodiment of the present disclosure, the light emitting layer includes a host and a dopant, and the light emitting layer includes the dopant to the host in a weight ratio of 0.1:99.9 to 20:80.
According to an embodiment of the present disclosure, the organic light emitting device includes an electron transport region disposed between the cathode and the light emitting layer.
According to an embodiment of the present specification, the organic light emitting device includes an electron transport region disposed between the cathode and the light emitting layer, the electron transport region including a compound represented by chemical formula 3 below.
[ Chemical formula 3]
In the above-mentioned chemical formula 3, a compound represented by formula 1,
X1 is N or CQ101, X2 is N or CQ102, X3 is N or CQ103,
At least one of the above X1 to X3 is N,
Q101 to Q103 and Q1 to Q3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a 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.
According to an embodiment of the present specification, the electron transport region may be used without limitation as long as it is a monocyclic six-membered heterocyclic compound, that is, a triazine derivative, a pyrimidine derivative, and a pyridine derivative.
According to an embodiment of the present specification, the electron transport region includes a compound represented by the above chemical formula 3, an organic alkali metal complex, and a mixture thereof. In this case, the organic alkali metal complex may be lithium quinolinate or aluminum quinolinate, but is not limited thereto, and the content of the organic alkali metal complex is 10 to 90wt%, preferably 30 to 70wt%, with respect to the material of the organic layer.
According to an embodiment of the present disclosure, the electron transport region includes an electron transport layer and an electron modulation layer.
According to an embodiment of the present specification, the organic light emitting device may include only the hole transport region and the light emitting layer as the organic layer, but may further include an additional organic layer. For example, additional hole injection layers, hole transport layers, electron blocking layers, light emitting layers, hole blocking layers, electron transport layers, electron injection layers, and the like may also be included.
According to an embodiment of the present specification, the organic light emitting device may further include an additional organic layer. The above-mentioned additional organic layer may have 1 or more of a light emitting layer, a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, an electron injecting layer, an electron transporting layer, an electron injecting and transporting layer, an electron adjusting layer, an electron blocking layer, a hole blocking layer, and a hole adjusting layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
In another embodiment, the organic light emitting device may be a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In another embodiment, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type (INVERTED TYPE)) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
In the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
In the organic light-emitting device of the present specification, the layer adjacent to the light-emitting layer among the organic layers includes the compound represented by the above chemical formula 1, and the light-emitting layer includes the compound represented by the above chemical formula 2, but may be manufactured using materials and methods known in the art.
For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. This can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a physical vapor deposition method (PVD: physical Vapor Deposition) such as sputtering or electron beam evaporation (e-beam evaporation), an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition to these methods, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (international patent application publication No. 2003/012890). However, the manufacturing method is not limited thereto.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; and multilayer structures such as LiF/Al, liO 2/Al, and Mg/Ag, but not limited thereto.
A capping layer for protecting the electrode may be further formed on the cathode, and materials used in the art may be appropriately used as the capping material.
The hole injection layer is a layer that injects holes from the electrode as a hole injection substance, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but are not limited thereto.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The hole blocking layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, and thus can improve the lifetime and efficiency of the device, and can be formed in an appropriate portion between the light emitting layer and the electron injection layer using a known material.
The light-emitting substance of the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and when the organic light-emitting device of the present specification includes an additional light-emitting layer in addition to the light-emitting layer containing the compound represented by the chemical formula 2, it is preferable that the organic light-emitting device has high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq 3); carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
An electron modulation layer may be further provided between the light emitting layer and the electron transport layer. The electronically adjusting layer substance may be suitably a material used in this technical field.
The electron transporting material of the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting material is a material that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is suitable for a material having high mobility of electrons. Specific examples include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/>Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
The structure according to an embodiment of the present specification can also function in an organic electronic device typified by an organic solar cell, an organic photoreceptor, an organic transistor, or the like, on a principle similar to that applied to an organic light-emitting device.
Modes for carrying out the invention
The fabrication of the above-described organic light emitting device is specifically described in the following examples. However, the following examples are given by way of illustration of the present specification, and the scope of the present specification is not limited thereto.
Preparation example (Synthesis of BH)
Reactant (1 equivalent), triflic acid (Trifluoromethanesulfonic acid) (catalyst (cat.)) was added to C 6D6 (10-50 times the mass ratio relative to the reactant), and stirred at 70 ℃ for 10 to 100 minutes. After the completion of the reaction, D 2 O (excess) was added, and after stirring for 30 minutes, trimethylamine (TRIMETHYLAMINE) (excess) was added dropwise. The reaction solution was transferred to a separating funnel, and extracted with water and chloroform. The extract was dried over MgSO 4 and then recrystallized by heating with toluene, whereby the following products of table 1 and table 2 were obtained.
TABLE 1
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The degree of substitution of deuterium varies depending on the reaction time of each product, and the substitution rate is determined based on the maximum M/z (M+) value.
The above reactants were synthesized with reference to the present company documents such as KR1964435, KR1899728, KR1975945, KR2018-0098122, KR2018-0102937, KR2018-0103352, etc. In addition, reference is made to the prior art document of KR1538534 for deuterium substitution of the above-mentioned products.
TABLE 2
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The degree of substitution of deuterium varies depending on the reaction time of each product, and the substitution rate is determined based on the maximum M/z (M+) value.
The above-mentioned reactants were synthesized with reference to the present documents of this company such as KR1994238B1, KR1670193B1, KR1754445B1, KR1368164B1, etc. In addition, reference is made to the prior art document of KR1538534B1 for deuterium substitution of the above-mentioned products.
In addition, compounds 1-21 to 1-22 and BH3 (deuterium substitution rate 0%), BH4 (deuterium substitution rate 25%) and BH5 (deuterium substitution rate 35%) having deuterium substitution rates of 40% and 65%, respectively, were synthesized with reference to the above-mentioned prior art documents, and comparative experiments were also conducted on compounds having different deuterium substitution rates.
The products of tables 1 and 2, compounds 1 to 21 and 1 to 22 were synthesized by reference JP4070676B2、KR1477844B1、US6465115B2、JP3148176B2、JP4025136B2、JP4188082B2、JP5015459B2、KR1979037B1、KR1550351B1、KR1503766B1、KR 0826364B1、KR0749631B1、KR1115255B1 and other prior art documents. In addition, deuterium (-D) incorporated into the products synthesized in tables 1 and 2 above means that it can be incorporated at the labeled position and does not mean that it must be incorporated at the labeled position.
In addition, the following compounds 3-1 to 3-18, which are compounds represented by the above chemical formula 1 contained in the following hole transport region, were synthesized with reference to JP 2015-5306364A, US5840217A, WO-120577A, KR 2016-0035610A.
< Comparative example 1-1> manufacture of organic light emitting device
As an anode, will beThe substrate on which ITO/Ag/ITO was deposited was cut into a size of 50 mm. Times.50 mm. Times.0.5 mm, and the substrate was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was filtered 2 times by a Filter (Filter) manufactured by millbore co., ltd. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the anode thus prepared, HI-1 was reacted withForming a hole injection layer by thermal vacuum deposition, wherein HT1 as a hole transporting substance is formed on the hole injection layer to have a thickness/>Vacuum evaporation is performed to form a hole transport layer. Next, EB1/>, is usedA hole-regulating layer was formed, and BH1 and a dopant BD1 (2 wt.%) were then added to the substrate to form a layer of a hole-regulating layerAnd vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Then, HB1 was vapor deposited/>And forming an electron-regulating layer by mixing the compounds ET1 and Liq at a ratio of 5:5 (mass ratio), thereby forming a thickness/>Is provided. Will/>, in turnMagnesium and lithium fluoride (LiF) as electron injection layer < EIL > are formed into film and then as cathode to/>Magnesium and silver (1:4) were formed, followed by CP1 evaporation/>Thereby completing the device. In the above process, the vapor deposition rate of the organic matter is maintained/>
/>
< Comparative examples 1-2 to 1-15 and examples 1-1 to 1-43>
In the above comparative example 1-1, the organic light emitting devices were manufactured in the same manner as in the above comparative example 1-1 except that the compounds of the following table 3 were used instead of BH1 as the main body of the light emitting layer and the compounds of the following table 3 were used instead of EB1 as the hole adjusting layer, respectively, the structures of the organic light emitting devices manufactured in the above comparative examples 1-1 to 1-15 and examples 1-1 to 1-43 were shown in the following table 3, and the following table 4 is the result of measuring the driving voltage, the light emitting efficiency, and the time (LT 95) of 95% with respect to the initial luminance at the current density of 20mA/cm 2 for the above comparative examples 1-1 to 1-15 and examples 1-1 to 1-43.
TABLE 3
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TABLE 4
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In tables 3 and 4 described above, the organic light emitting device according to an embodiment of the present specification shows excellent hole injection and transport ability to the light emitting layer by using the compound of chemical formula 1 applicable to the hole transport region of the blue organic electroluminescent device and chemical formula 2 used as a host of the light emitting layer. Further, by balancing holes and electrons of the organic light emitting device according to the chemical structure, the organic light emitting device according to the present specification shows superior characteristics in terms of efficiency, driving voltage, stability, as compared with the organic light emitting device including chemical formula 1 or chemical formula 2, respectively.
In particular, the results regarding the device characteristics of deuterium substitution rate according to the above chemical formula 2 can also be observed from the results of the above tables 3 to 4. Comparative examples 1 to 11 to 1 to 13 using compounds 1 to 6, in which the deuterium substitution rate was unsubstituted (0%), 20%, and 35%, respectively, showed significantly lower lifetimes than examples 1 to 6, 1 to 42, and 1 to 43 using compounds in which the deuterium substitution rate was 40% or more, and it was found that the effect of increasing the lifetime according to deuterium substitution was not exhibited. In contrast, examples 1 to 6, 1 to 42 and 1 to 43, in which the deuterium substitution rate of the chemical formula 2 is 40% or more, have a significantly improved lifetime as compared with comparative examples 1 to 11 to 1 to 13, and it is understood that the deuterium substitution rate of the chemical formula 2 is 40% or more and the lifetime of the device is significantly improved.
In addition, when comparing examples 1 to 42 and 1 to 43 with comparative examples 1 to 14 and 1 to 15, it was found that the life of examples 1 to 42 and 1 to 43, in which deuterium substitution rate of chemical formula 2 was 40% or more, was greatly increased, and efficiency and driving voltage were also excellent.
< Comparative example 2-1> manufacture of organic light emitting device
As an anode, will beThe substrate on which ITO/Ag/ITO was deposited was cut into a size of 50 mm. Times.50 mm. Times.0.5 mm, and the substrate was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of feiher company, and distilled water was filtered 2 times by a filter manufactured by milbo company. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the anode thus prepared, HI-1 was reacted withForming a hole injection layer by thermal vacuum deposition, wherein HT1 as a hole transporting substance is formed on the hole injection layer to have a thickness/>Vacuum evaporation is performed to form a hole transport layer. Next, EB1/>, is usedA hole-regulating layer was formed, and BH1 and a dopant BD2 (2 wt.%) were then added to the substrate to form a layer of a hole-regulating layerAnd vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Then, HB1 was vapor deposited/>And forming an electron-regulating layer by mixing the compounds ET1 and Liq at a ratio of 5:5 (mass ratio), thereby forming a thickness/>Is provided. Will/>, in turnMagnesium and lithium fluoride (LiF) as electron injection layer < EIL > are formed into film and then as cathode to/>Magnesium and silver (1:4) were formed, followed by CP1 evaporation/>Thereby completing the device. In the above process, the vapor deposition rate of the organic matter is maintained/>/>
/>
< Comparative examples 2-2 to 2-10 and examples 2-1 to 2-41>
In the above comparative example 2-1, the organic light emitting devices were produced in the same manner as in the above comparative example 2-1 except that the compounds of the following table 5 were used as the main body of the light emitting layer instead of BH1 and the compounds of the following table 5 were used as the hole adjusting layer instead of EB1, respectively, and the structures of the organic light emitting devices produced in the above comparative examples 2-1 to 2-10 and examples 2-1 to 2-41 were shown in the following table 5, and the following table 6 is the result of measuring the driving voltage, the light emitting efficiency, and the time (LT 95) of 95% with respect to the initial luminance at the current density of 20mA/cm 2 for the above comparative examples 2-1 to 2-10 and examples 2-1 to 2-41.
TABLE 5
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TABLE 6
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In the above tables 3 to 6, the organic light emitting device according to an embodiment of the present specification shows excellent hole injection and transport ability to the light emitting layer by using the compound of chemical formula 1 applicable to the hole transport region of the blue organic electroluminescent device and chemical formula 2 used as the light emitting layer host. Further, by balancing holes and electrons of the organic light emitting device according to the chemical structure, the organic light emitting device according to the present specification shows superior characteristics in terms of efficiency, driving voltage, stability, as compared with the organic light emitting device including chemical formula 1 or chemical formula 2, respectively.
The above examples 1-1 to 1-38, 1-42, 1-43, and 2-1 to 2-38 used the compound of the above chemical formula 1 alone as a hole transport layer and the compound of the above chemical formula 2 alone as a host of a light emitting layer, thereby producing devices. The device structure shows that BD1 or BD2 can be applied to various hole-adjusting layers corresponding to chemical formula 1 and various blue host and blue fluorescent dopants corresponding to chemical formula 2. Further, examples 1-39 to 1-41 and 2-39 to 2-41 show that 2 kinds of hosts corresponding to chemical formula 2 are used as a mixed host, whereby the performance of the device can be improved.
The above comparative examples 1-1 to 1-6, 1-11 to 1-13, and 2-1 to 2-6 are the results of devices made with compounds other than the combination of the compounds 1 and 2 according to an embodiment of the present specification, and anthracene of the aryl group series was used as the main body of the light-emitting layer. This situation all shows high voltage, low efficiency, low lifetime, and low device performance.
The above comparative examples 1-7, 1-8, 1-14, 1-15, 2-7 and 2-8 are results of applying only the hole adjusting layer corresponding to the above chemical formula 1, and a small driving voltage drop trend can be observed as compared with comparative examples 1-1 to 1-6, 1-11 to 1-13 and 2-1 to 2-6, but it can be seen that the overall device performance improvement is not achieved. Further, the above comparative examples 1-9, 1-10, 2-9 and 2-10 are the results of applying only the blue main body corresponding to the above chemical formula 2, and an improvement in the overall life can be observed as compared with comparative examples 1-1 to 1-6, 1-11 to 1-13 and 2-1 to 2-6.
In comparison with the above-described 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, due to the combination of chemical formulas 1 and 2 of the present specification, carriers of the device, particularly holes, are easily injected into the body, thereby functioning to grasp the balance of the device, showing that the device performance can be improved as a whole.
Examples 2-1 to 2-41 described above are the results of devices to which BD2 and the combination of chemical formulas 1 and 2 of the present specification are applied, and it can be observed that the device balance of the combination is also excellent when various types of blue dopants are introduced.

Claims (23)

1. An organic light emitting device comprising:
An anode;
a cathode;
A light emitting layer disposed between the anode and the cathode; and
A hole transport region including 2 or more organic layers disposed between the light emitting layer and the anode,
The organic layer connected to the light emitting layer among the organic layers includes a compound represented by the following chemical formula 1,
The light emitting layer includes a compound represented by the following chemical formula 2:
Chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
Any one of R8 and R9 is a group represented by the following formula a, groups other than the group represented by the following formula a in R8 and R9, R1 to R7 and R10 to R18 are the same or different from each other, each is independently hydrogen, deuterium, 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, or groups other than the group represented by the following formula a in R8 and R9, R1 to R6, R7, and adjacent groups in R10 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring,
Chemical formula a
In the chemical formula a, in which the amino acid is represented by formula a,
L1 to L3 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
Ar1 and Ar2 are the same or different from each other and are each independently deuterium, a halogen group, a hydroxyl group, a cyano group, a 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,
11. 12 And 13 are each integers of 1 to 3,
When 11 is 2 or more, 2 or more L1 s are the same or different from each other,
When 12 is 2 or more, 2 or more L2 s are the same or different from each other,
When 13 is 2 or more, 2 or more L3 s are the same or different from each other,
Represents a site to which R8 or R9 of the chemical formula 1 is bonded,
Chemical formula 2
In the chemical formula 2 described above, the chemical formula,
At least one of G1 to G10 is a group represented by the following formula b, the others being the same or different from each other, each independently being hydrogen, deuterium, or a substituted or unsubstituted aryl group,
Chemical formula b
In the chemical formula b, in which the amino acid is represented by formula b,
A and B are the same or different from each other and are a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,
L4 is a direct bond, or a substituted or unsubstituted arylene,
14 Is an integer of 1 to 3,
When 14 is 2 or more, 2 or more L4 s are the same or different from each other,
Represents a site to which at least one of G1 to G10 of the chemical formula 2 is bound,
The deuterium substitution rate of chemical formula 2 is 40% to 100%.
2. The organic light-emitting device according to claim 1, wherein the deuterium substitution rate of chemical formula 2 is 40% to 99%.
3. The organic light-emitting device according to claim 1, wherein the deuterium substitution rate of chemical formula 1 is 1% to 100%.
4. The organic light-emitting device according to claim 1, wherein any one of R8 and R9 is a group represented by the formula a, the group other than the group represented by the formula a, R1 to R7, and R10 to R18 in R8 and R9 are the same or different from each other, each is independently hydrogen, deuterium, 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, or the group other than the group represented by the formula a, R1 to R6, R7, and R10 to R18 in R8 and R9 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
5. The organic light-emitting device according to claim 1, wherein the L1 to L3 are the same or different from each other, each independently being a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is substituted or unsubstituted with 1 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 substituted or unsubstituted with deuterium, or a linear or branched alkyl group having 1 to 30 carbon atoms.
6. The organic light-emitting device according to claim 1, wherein Ar1 and Ar2 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms substituted with 1 or more than 1 selected from deuterium, a linear or branched alkyl group of 1 to 30 carbon atoms substituted with deuterium, a linear or branched alkylsilyl group of 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 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.
7. The organic light-emitting device according to claim 1, wherein at least one of G1 to G10 is a group represented by the formula b, and the others are the same or different from each other, each being independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium.
8. The organic light-emitting device according to claim 1, wherein the L4 is a monocyclic or polycyclic arylene group of 6 to 30 carbon atoms, which is directly bonded, or substituted or unsubstituted with deuterium.
9. The organic light-emitting device according to claim 1, wherein the a and B are the same or different from each other, each independently is a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more of monocyclic or polycyclic aromatic hydrocarbon rings of 6 to 30 carbon atoms selected from deuterium, and substituted or unsubstituted with deuterium; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium.
10. The organic light-emitting device according to claim 1, wherein the chemical formula 1 is any one selected from the following compounds:
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11. the organic light-emitting device according to claim 1, wherein the chemical formula 2 is any one selected from the following compounds:
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12. The organic light-emitting device according to claim 1, wherein an organic layer connected to the anode among the organic layers contains a carbazole-based compound.
13. The organic light-emitting device according to claim 1, wherein the organic layer comprises a hole transport layer and a hole adjustment layer, the hole transport layer comprising the compound represented by chemical formula 1.
14. The organic light-emitting device according to claim 1, wherein the triplet energy of chemical formula 1 is 2.4eV to 2.8eV.
15. The organic light-emitting device according to claim 1, wherein the light-emitting layer comprises a host comprising the compound represented by chemical formula 2 and a dopant.
16. The organic light-emitting device according to claim 1, wherein the light-emitting layer comprises 2 or more mixed hosts, and 1 or more of the 2 or more mixed hosts comprise the compound represented by chemical formula 2.
17. The organic light-emitting device according to claim 1, wherein the light-emitting layer comprises 2 or more mixed hosts, at least 1 of the 2 or more mixed hosts comprises a compound represented by the chemical formula 2, and the balance comprises 1 or more selected from an anthracene-based compound that does not include deuterium as a substituent, and an anthracene-based compound that includes deuterium as a substituent and is different from the chemical formula 2.
18. The organic light-emitting device according to claim 1, wherein a maximum emission wavelength λ Maximum value of an emission spectrum of the organic light-emitting device is 400nm to 470nm.
19. An organic light-emitting device according to claim 1 wherein the light-emitting layer comprises a host and a dopant, the dopant being a fluorescent dopant.
20. The organic light-emitting device according to claim 1, wherein the light-emitting layer comprises a host and a dopant comprising 1 or more selected from pyrene-based compounds and non-pyrene-based compounds.
21. The organic light-emitting device according to claim 20, wherein the non-pyrene compound comprises a boron compound.
22. The organic light-emitting device according to claim 1, wherein the organic light-emitting device comprises an electron transport region disposed between the cathode and the light-emitting layer, the electron transport region comprising a compound represented by the following chemical formula 3:
Chemical formula 3
In the chemical formula 3 described above, the chemical formula,
X1 is N or CQ101, X2 is N or CQ102, X3 is N or CQ103,
At least one of X1 to X3 is N,
Q101 to Q103 and Q1 to Q3 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a 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. The organic light-emitting device of claim 22, wherein the electron transport region comprises a compound represented by the chemical formula 3, an organic alkali metal complex, and mixtures thereof.
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