KR102655907B1 - Organic light emitting device - Google Patents

Abstract

This specification includes an anode; cathode; A light emitting layer provided between the anode and the cathode; And an organic light-emitting device comprising a hole transport region including two or more organic material layers provided between the light-emitting layer and the anode, wherein an organic material layer in contact with the light-emitting layer among the organic material layers contains a compound of Formula 1, and the light-emitting layer has a compound of Formula 2 It relates to an organic light-emitting device containing a compound.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0007105 filed with the Korea Intellectual Property Office on January 20, 2020, the entire contents of which are incorporated herein by reference.

This specification relates to organic light emitting devices.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.

The development of new materials for organic light-emitting devices as described above continues to be required.

Korean Patent Publication No. 2000-0051826

This specification provides an organic light emitting device.

An exemplary embodiment of the present specification includes an anode; cathode; A light emitting layer provided between the anode and the cathode; And an organic light-emitting device comprising a hole transport region including two or more organic material layers provided between the light-emitting layer and the anode, wherein the organic material layer in contact with the light-emitting layer among the organic material layers includes a compound represented by the following formula (1), and the light-emitting layer includes: An organic light emitting device comprising a compound represented by the following formula (2) is provided.

[Formula 1]

In Formula 1,

One of R8 and R9 is a group represented by the following formula (a), and among R8 and R9, a group other than the group represented by the formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or a group among R8 and R9 that is not a group represented by the following formula (a), and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring. can form,

[Formula a]

In formula a,

L1 to L3 are the same or different from each other and are each independently directly bonded; 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; halogen group; hydroxyl group; Cyano group; nitro group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

l1 to l3 are each integers from 1 to 3,

When l1 is 2 or more, the 2 or more L1 are the same or different from each other,

When l2 is 2 or more, L2 of 2 or more is the same or different from each other,

When the l3 is 2 or more, the 2 or more L3s are the same or different from each other,

means a site bound to R8 or R9 of Formula 1,

[Formula 2]

In Formula 2,

At least one of G1 to G10 is a group represented by the following formula (b), the others are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; Cyano group; nitro group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

[Formula b]

In formula b,

A and B are the same or different and are substituted or unsubstituted hydrocarbon rings; Or a substituted or unsubstituted heterocycle,

L4 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

l4 is an integer from 1 to 3,

When l4 is 2 or more, the 2 or more L4 are the same or different from each other,

means a site bound to at least one of G1 to G10 of Formula 2,

The deuterium substitution rate of Formula 2 is 40% to 100%.

The organic light-emitting device according to an exemplary embodiment of the present specification includes the compound of Formula 1 in the organic material layer in contact with the light-emitting layer, and the compound of Formula 2 in the light-emitting layer, so the driving voltage is low, luminous efficiency is improved, and the thermal stability of the compound is low. This can improve the lifespan characteristics of the device.

1 to 4 show examples of organic light-emitting devices according to an exemplary embodiment of the present specification.
Figure 5 is a diagram showing the MS graph of Compound A.

Hereinafter, this specification will be described in more detail.

As used herein, “deuterated” or “deuterated” means that hydrogen at a replaceable position in a compound is replaced with deuterium.

As used herein, “perdeuterated” means a compound or group in which all hydrogens in the molecule are replaced with deuterium, and has the same meaning as “100% deuterated.”

As used herein, “X% deuterated”, “Deuteration degree X%”, or “Deuterium substitution rate X%” means that For example, if the structure in question is dibenzofuran, the dibenzofuran is “25% deuterated,” the “deuteration degree of 25%” of the dibenzofuran, or the “deuterium substitution rate of 25%” of the dibenzofuran is defined as the above. This means that two of the eight hydrogens at the replaceable positions of dibenzofuran have been replaced with deuterium.

In this specification, “degree of deuteration” or “deuterium substitution rate” refers to nuclear magnetic resonance spectroscopy ( ¹ H NMR), TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), or GC/MS (Gas Chromatography/Mass Spectrometry), etc. It can be confirmed by a publicly known method.

Specifically, when analyzing the “degree of deuteration” or “deuterium substitution rate” by nuclear magnetic resonance spectroscopy ( ¹ H NMR), DMF (dimethylformamide) is added as an internal standard to determine the integration ratio on ¹ H NMR. Through this, the degree of deuteration or deuterium substitution rate can be calculated from the integrated amount of the total peak.

In addition, when analyzing the “degree of deuteration” or “deuterium substitution rate” through TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), the substitution rate is determined based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. It can be calculated. For example, when analyzing the degree of deuteration of Compound A below, the molecular weight of the starting material below is 506, and the maximum molecular weight (median value) of Compound A below in the MS graph of Figure 5 is 527, the possible substitution of the starting material below is 527. Since 21 of the hydrogen positions (26) were replaced with deuterium, it can be calculated that about 81% of the hydrogens were deuterated.

In this specification, D means deuterium.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In this specification, the 'layer' is interchangeable with the 'film' mainly used in the present technical field, and refers to a coating that covers the target area. The size of the 'layer' is not limited, and each 'layer' may be the same or different in size. According to one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

In this specification, the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.

In this specification, the meaning that a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.

In this specification, "or" refers to a comprehensive 'or' and does not mean an exclusive 'or'. For example, condition A or B is satisfied by either: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), both A and B are true (or exist).

In this specification, “mixture thereof” or “mixture” means that two or more types of substances are included. The “mixture” or “mixture” may include a uniformly and/or non-uniformly mixed state, a dissolved state, a uniformly and/or non-uniformly dispersed state, etc., but is not limited thereto.

Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will control unless a specific passage is mentioned. Moreover, the materials, methods, and examples are illustrative only and are not intended to be limiting.

Examples of substituents in this specification are described below, but are not limited thereto.

In this specification, means the connected part.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

As used herein, the term “substituted or unsubstituted” refers to 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; It means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.

In this specification, linking two or more substituents means that the hydrogen of one substituent is linked to another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected. or It can be a substituent of . In addition, connecting three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also (substituent 2) and (substituent 3) are connected to (substituent 1). Includes. For example, a phenyl group, a naphthyl group, and an isopropyl group are connected, , or It can be a substituent of . The above definition equally applies to those in which 4 or more substituents are connected.

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl. , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. , but is not limited to this.

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n. -It can be hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It is not limited.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

If the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable to have 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.

In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.

When the fluorene group is substituted, etc., but is not limited to this.

As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.

In the present specification, the heteroaryl group includes one or more non-carbon atoms and heteroatoms. Specifically, the heteroaryl group may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, and acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzyl group. Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group, phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spirofluorenexanthene group and spirofluorene. Thioxanthene group, etc., but is not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. Among the alkylsilyl groups, examples of the alkyl group described above may be applied to the alkyl group, examples of the aryl group described above may be applied to the aryl group among the arylsilyl groups, and examples of the heteroaryl group among the heteroarylsilyl groups may apply to the heteroaryl group. can be applied.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , where R ₁₀₀ and R ₁₀₁ are the same or different, and are each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.

In the present specification, the amine group is -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre Examples include, but are not limited to, a nylfluorenylamine group and an N-biphenylfluorenylamine group.

In the present specification, N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group. The alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.

In the present specification, N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.

In the present specification, N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heteroaryl group described above.

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched alkyl group. The alkylamine group containing two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or both a straight-chain alkyl group and a branched-chain alkyl group. For example, the alkyl group in the alkylamine group may be selected from the examples of alkyl groups described above.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously. For example, the aryl group in the arylamine group may be selected from the examples of aryl groups described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of heteroaryl groups described above.

In the present specification, “two adjacent substituents combine with each other to form a ring” means a substituted or unsubstituted hydrocarbon ring with adjacent groups bonded with each other; Or it means forming a substituted or unsubstituted heterocycle.

In the present specification, in substituted or unsubstituted rings formed by combining each other, “ring” refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from examples of the cycloalkyl group or aryl group, excluding those that are not monovalent.

In the present specification, a heterocycle includes one or more non-carbon atoms and heteroatoms. Specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, etc., but is not limited thereto.

In the present specification, an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group.

In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a bivalent group. The description of the heteroaryl group described above can be applied, except that each of these is a divalent group.

An organic light emitting device according to an exemplary embodiment of the present specification includes an anode; cathode; A light emitting layer provided between the anode and the cathode; And an organic light-emitting device comprising a hole transport region including two or more organic material layers provided between the light-emitting layer and the anode, wherein the organic material layer in contact with the light-emitting layer among the organic material layers includes a compound represented by the following formula (1), and the light-emitting layer includes: It includes a compound represented by the following formula (2). At this time, the deuterium substitution rate of the compound of Formula 2 is 40% to 100%.

The organic light-emitting device according to the above embodiment is characterized in that it contains the compound of Formula 1 between the anode and the light-emitting layer, that is, in the hole transport region, and the compound of Formula 2 in the light-emitting layer. By including the compound of Formula 1 in the hole transport region of the organic light-emitting device, the efficiency of the light-emitting layer can be increased by speeding up injection and transport of holes and maximizing carrier transport into the light-emitting layer, and by including the compound of Formula 2 in the light-emitting layer. , a device with excellent lifespan can be obtained.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 40% to 100%, and preferably 40% to 99%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 45% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 50% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 65% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 70% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 80% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 90% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 2 is 100%.

The deuterium substitution rate can be calculated by the method described above. According to a further example, at least one deuterium is directly substituted on the anthracene of Formula 2 above. The light-emitting layer of an organic light-emitting device is a region that emits light and is a section in which molecular loss due to energy is large. The carbon-deuterium bond is stronger than the carbon-hydrogen bond, and since deuterium has a higher mass value than hydrogen, the zero point energy with carbon is lowered and the bond energy is high, so the molecule of the compound of formula 2 By replacing the carbon-hydrogen bonds contained within with carbon-deuterium bonds, the bond energy of the molecule can be increased to obtain a device with excellent lifespan.

Zero point energy =

The lifespan of an organic light-emitting device containing the compound of Formula 2 having a deuterium substitution rate according to an exemplary embodiment of the present specification has the effect of improving the device lifespan.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 1 is 0% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 1 is 0.01% to 100%.

According to an exemplary embodiment of the present specification, the deuterium substitution rate of Formula 1 is 1% to 100%.

According to an exemplary embodiment of the present specification, at least one of the hydrogens at the substitutable positions in Formula 1 is replaced with deuterium.

According to an exemplary embodiment of the present specification, one of R8 and R9 is a group represented by the formula (a), and among the R8 and R9, a group other than the group represented by the formula (a), R1 to R7 and R10 to R18 are each other. Same or different, each independently hydrogen; heavy hydrogen; A straight 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 among R8 and R9 that is not a group represented by the following formula (a), and adjacent groups among R1 to R6, R7, and R10 to R18 are each other. By combining, they form a polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the adjacent groups among R8 and R9, which are not groups represented by the following formula (a), R1 to R6, R7, and R10 to R18, are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring. form

According to an exemplary embodiment of the present specification, the adjacent groups among R8 and R9, which are not groups represented by the following formula (a), R1 to R6, R7, and R10 to R18, are bonded to each other and have 6 to 20 substituted or unsubstituted carbon atoms. It forms an aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, the adjacent groups among R8 and R9, which are not groups represented by the following formula (a), R1 to R6, R7, and R10 to R18, are bonded to each other to form a substituted or unsubstituted benzene ring. do.

According to an exemplary embodiment of the present specification, the adjacent groups among R8 and R9, groups other than those represented by the formula (a), R1 to R6, R7, and R10 to R18 combine with each other to form a benzene ring.

According to an exemplary embodiment of the present specification, R1 and R18 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, R1 and R18 are combined with each other to form a substituted or unsubstituted polycyclic aromatic hydrocarbon ring having 13 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R18 are combined with each other to form a substituted or unsubstituted fluorene ring.

According to an exemplary embodiment of the present specification, R1 and R18 are combined with each other to form an aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, R1 and R18 are combined with each other to form a polycyclic aromatic hydrocarbon ring having 13 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R18 are combined with each other to form a fluorene ring.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

R2 to R17, R101 and R118 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

The definitions of L1 to L3, l1 to l3, Ar1, and Ar2 are the same as those defined in formula (a) above.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alkyl group; Or it is an aryl group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 10 carbon atoms; Or it is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms that is substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; tert-butyl group; Or it is a phenyl group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R7, R11, and R13 to R18 are hydrogen.

According to an exemplary embodiment of the present specification, R12 is hydrogen; tert-butyl group; Or it is a phenyl group.

According to an exemplary embodiment of the present specification, among R8 and R9, groups other than those represented by the following formula (a), R1 to R6, and R12 to R18 are hydrogen.

According to an exemplary embodiment of the present specification, R7 is a phenyl group substituted with deuterium.

According to an exemplary embodiment of the present specification, l1 is 1.

According to an exemplary embodiment of the present specification, l1 is 2.

According to an exemplary embodiment of the present specification, l2 is 1.

According to an exemplary embodiment of the present specification, l3 is 1.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; An arylene group substituted or unsubstituted with one or more selected from deuterium, an alkyl group, and an aryl group; Or it is a heteroarylene group substituted or unsubstituted with deuterium or an alkyl group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with one or more selected from deuterium, a straight 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 that is substituted or unsubstituted with deuterium, or a straight or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, substituted or unsubstituted with one or more selected from deuterium, a straight or branched chain alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium, or a straight or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Terphenylylene group substituted or unsubstituted with deuterium; A divalent fluorene group substituted with one or more selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a divalent benzofuran group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Terphenylylene group substituted or unsubstituted with deuterium; A divalent fluorene group substituted with one or more selected from deuterium, methyl group, and phenyl group; Or it is a divalent benzofuran group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Biphenylylene group; Terphenylylene group; A divalent fluorene group substituted with one or more selected from a methyl group and a phenyl group; Or it is a divalent benzofuran group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Arylene group substituted or unsubstituted with deuterium; Or it is a heteroarylene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A monocyclic or polycyclic arylene group having 6 to 15 carbon atoms substituted or unsubstituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Or it is a divalent benzofuran group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A phenylene group substituted or unsubstituted with deuterium; Biphenylylene group; Or it is a divalent benzofuran group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; Or, it is an arylene group substituted or unsubstituted with one or more selected from deuterium, an alkyl group, and an aryl group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is substituted or unsubstituted with one or more selected from deuterium, a straight 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 exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is substituted or unsubstituted with one or more selected from deuterium, a straight 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 exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Terphenylylene group substituted or unsubstituted with deuterium; or a divalent fluorene group substituted with one or more selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Terphenylylene group substituted or unsubstituted with deuterium; or a divalent fluorene group substituted with one or more selected from deuterium, methyl group, and phenyl group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Biphenylylene group; Terphenylylene group; or a divalent fluorene group substituted with one or more selected from a methyl group and a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium. A monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with one or more selected from the group consisting of an alkyl group, a straight or branched alkylsilyl group with 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms. energy; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, at least one selected from deuterium, a straight 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 exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium. a phenyl group substituted or unsubstituted with one or more selected from the group consisting of an alkyl group, and a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms; A biphenyl group substituted or unsubstituted with one or more selected from deuterium and straight-chain or branched-chain alkyl groups having 1 to 30 carbon atoms; Terphenyl group; Quarterphenyl group; Naphthyl group substituted or unsubstituted with deuterium; A phenanthrene group substituted or unsubstituted with deuterium; triphenylene group; Substituted with one or more selected from the group consisting of deuterium, a straight-chain or branched alkyl group with 1 to 30 carbon atoms, a straight-chain or branched alkyl group with 1 to 30 carbon atoms substituted with deuterium, and a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms. fluorene group; carbazole group; Dibenzofuran group; A benzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with one or more selected from deuterium, tert-butyl group, trimethylsilyl group, methyl group, and phenyl group; A biphenyl group substituted or unsubstituted with one or more selected from deuterium and tert-butyl groups; Terphenyl group; Quarterphenyl group; Naphthyl group substituted or unsubstituted with deuterium; A phenanthrene group substituted or unsubstituted with deuterium; triphenylene group; A fluorene group substituted with one or more selected from deuterium, trituterium methyl group, methyl group, and phenyl group; carbazole group; Dibenzofuran group; A benzofuran group substituted or unsubstituted with a phenyl group; Or it is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, R101 and R118 are hydrogen.

According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following formula (b), the others are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following formula (b), the others are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following formula (b), the others are the same or different from each other, and are each independently hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with one or more selected from deuterium and a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following formula (b), the others are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A phenyl group substituted or unsubstituted with one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; A naphthyl group substituted or unsubstituted with one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; A biphenyl group substituted or unsubstituted with one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; Terphenyl group substituted with deuterium; A phenanthrene group substituted or unsubstituted with deuterium; A triphenylene group substituted or unsubstituted with deuterium; Or it is a pyrene group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, at least one of G1 to G10 is a group represented by the following formula (b), the others are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A phenyl group substituted or unsubstituted with one 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 naphthyl group substituted or unsubstituted with one or more selected from deuterium, heavy hydrogen, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with deuterium; A biphenyl group substituted or unsubstituted with one or more selected from deuterium and phenyl groups substituted or unsubstituted with deuterium; Terphenyl group substituted with deuterium; A phenanthrene group substituted or unsubstituted with deuterium; Triphenylene group substituted or unsubstituted with deuterium; Or it is a pyrene group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, G1 is a group represented by the formula (b).

According to an exemplary embodiment of the present specification, G3 is a group represented by the formula (b).

According to an exemplary embodiment of the present specification, G1 and G6 are the same or different from each other and are each group represented by the formula (b).

According to an exemplary embodiment of the present specification, l4 is 1.

According to an exemplary embodiment of the present specification, L4 is a direct bond; Or it is a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L4 is a direct bond; Or it is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L4 is a direct bond; Or it is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L4 is a direct bond; Or it is a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L4 is a direct bond; Or it is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, L4 is a direct bond; Or it is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, L4 is a direct bond; A phenylene group substituted or unsubstituted with deuterium; Or it is a naphthylene group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocycle.

According to an exemplary embodiment of the present specification, A and B are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A and B are the same or different from each other, and are each independently one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium. A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, A and B are the same or different from each other, and are each independently one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium. Substituted or unsubstituted benzene ring; Naphthalene ring substituted or unsubstituted with deuterium; A phenanthrene ring substituted or unsubstituted with deuterium; A triphenylene ring substituted or unsubstituted with deuterium; Or it is a dibenzofuran ring substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, A and B are the same or different from each other, and are each independently deuterium, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and substituted or unsubstituted with deuterium. A benzene ring substituted or unsubstituted with one or more selected from ringed naphnyl groups; Naphthalene ring substituted or unsubstituted with deuterium; A phenanthrene ring substituted or unsubstituted with deuterium; A triphenylene ring substituted or unsubstituted with deuterium; Or it is a dibenzofuran ring substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds.

According to an exemplary embodiment of the present specification, Formula 2 is any one selected from the following compounds.

.

According to an exemplary embodiment of the present specification, the compounds of Formulas 1 and 2 can be prepared using starting materials and reaction conditions known in the art. The type and number of substituents can be determined by those skilled in the art by appropriately selecting known starting materials. Additionally, the compounds of Formulas 1 and 2 can be obtained from commercial sources.

According to an exemplary embodiment of the present specification, the organic material layer in contact with the anode among the organic material layers includes a carbazole-based compound.

According to an exemplary embodiment of the present specification, the carbazole-based compound may be represented by the following structural formula, but is not limited thereto.

In the above structural formula,

T1 to T3 are the same or different from each other, and are each independently 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; Or it is a heteroaryl group, or adjacent groups can be combined with each other to form a substituted or unsubstituted ring,

t1 is an integer from 1 to 4, and when t1 is 2 or more, 2 or more T1 are the same or different from each other,

t2 is an integer from 1 to 4, and when t2 is 2 or more, 2 or more T2 are the same or different from each other,

t3 is an integer from 1 to 10, and when t3 is 2 or more, 2 or more T3 are the same or different from each other.

According to an exemplary embodiment of the present specification, the carbazole-based compound may be selected from the following compounds, but is not limited thereto.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole transport layer and a hole control layer, and the hole transport layer includes the compound represented by Formula 1.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole transport layer and a hole control layer, and the hole control layer includes a compound represented by Formula 1.

The hole control layer according to an exemplary embodiment of the present specification includes a compound represented by Formula 1, and the deuterium substitution rate of Formula 1 is 1% to 100%.

According to an exemplary embodiment of the present specification, a hole transport region including the hole transport layer and the hole control layer is included between the anode and the light emitting layer, and the hole transport layer and the hole control layer are provided in contact with each other.

According to an exemplary embodiment of the present specification, the hole control layer is provided in contact with the light-emitting layer.

According to an exemplary embodiment of the present specification, a hole injection layer may be included between the anode and the hole transport layer.

The structure of the organic light emitting device of the present specification may have, for example, the structure shown in FIGS. 1 to 4, but is not limited thereto.

Figure 1 illustrates the structure of an organic light emitting device in which an anode (2), a hole transport region (3), a light emitting layer (4), and a cathode (5) are sequentially stacked on a substrate (1). 1 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

In Figure 2, a hole transport region (3) including an anode (2), a hole transport layer (3-1), and a hole control layer (3-2), a light emitting layer (4), and a cathode (5) are sequentially placed on the substrate (1). The structure of a stacked organic light emitting device is illustrated. 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

3 shows an anode (2), a hole injection layer (6), a hole transport region (3), a light emitting layer (4), an electron transport region (7), an electron injection layer (8), and a cathode (5) on the substrate (1). The structure of an organic light emitting device in which are sequentially stacked is illustrated. 3 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

4 shows a hole transport region (3) including an anode (2), a hole injection layer (6), a hole transport layer (3-1), and a hole control layer (3-2) on a substrate (1), and a light emitting layer (4). , an example of the structure of an organic light-emitting device in which an electron transport region (7) including an electron control layer (7-1) and an electron transport layer (7-2), an electron injection layer (8), and a cathode (5) are sequentially stacked. It is done. 4 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

According to an exemplary embodiment of the present specification, the thickness of the hole transport layer is 50 nm to 200 nm.

According to an exemplary embodiment of the present specification, the thickness of the hole control layer is 10 nm to 150 nm.

The hole transport region is composed of multiple or single layers including a hole transport layer and a hole control layer. In order to optimize the optical properties of the organic light emitting device, the thickness of the hole transport region can be determined based on the optimal point within the thickness. .

According to an exemplary embodiment of the present specification, the triplet energy of Chemical Formula 1 is 2.4 eV to 2.8 eV.

When the layer in contact with the light-emitting layer in the hole transport region according to an exemplary embodiment of the present specification, that is, the layer containing Formula 1, has the triplet energy range, it typically exhibits a relatively high singlet energy, and accordingly, the low It is common to have the highest occupied orbital energy. Therefore, since carrier and exciton movement or transition in the light emitting layer is not easy, the efficiency of the manufactured organic light emitting device can be increased and stability can be achieved.

In this specification, “energy level” means energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, a low or deep energy level means that the absolute value increases in the minus direction from the vacuum level.

In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital (highest occupied molecular orbital) in the region with the highest energy in the region where electrons can participate in bonding, and LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (lowest unoccupied molecular orbital) in which an electron is in the lowest energy region of the antibonding region, and the HOMO energy level refers to the distance from the vacuum level to HOMO. Additionally, the LUMO energy level refers to the distance from the vacuum level to the LUMO. A determined structure is necessary to determine the distribution of electrons within a molecule and its optical properties. Additionally, the electronic structure has different structures in neutral, anionic, and cationic states depending on the charge state of the molecule. For the operation of a device, the energy levels of the neutral state, positive ion, and negative ion state are all important, but typically, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in the neutral state are recognized as important physical properties. To determine the molecular structure of a chemical substance, the input structure is optimized using density functional theory. For DFT calculation, BPW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and DNP (double numerical basis set including polarization functional) basis set are used. The BPW91 calculation method is described in the paper A. D. Becke, Phys. Rev. A, 38, 3098 (1988)' and 'J. P. Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992), and the DNP basis set is published in the paper 'B. Delley, J. Chem. Phys., 92, 508 (1990).

To perform calculations using the pan-density function method, Biovia's 'DMol3' package can be used. If the optimal molecular structure is determined using the method given above, the energy level that can be occupied by electrons can be obtained as a result.

In this specification, triplet energy refers to an electronic state in a molecule with a spin quantum number of 1. The triplet energy is calculated by calculating the energy levels of the singlet and triplet using time dependent density functional theory (TD-DFT) to determine the excited state physical properties for the optimal molecular structure determined by the above-described method. Calculate. Calculation of the pan-density function can be performed using the 'Gaussian09' package, a commercial calculation program developed by Gaussian. To calculate the time-dependent pan-density function, the B3PW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and the 6-31G* basis set are used. The 6-31G* basis set is described in the paper 'J. A. Pople et al., J. Chem. Phys. 56, 2257 (1972). For the optimal molecular structure determined using the full-density function method, the energy when the electronic configuration is singlet and triplet is calculated using the time-dependent full-density function method (TD-DFT).

According to an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant.

According to an exemplary embodiment of the present specification, it includes the host and a dopant, and the host includes the compound represented by Formula 2.

According to an exemplary embodiment of the present specification, the dopant is a blue dopant.

According to an exemplary embodiment of the present specification, the organic light emitting device is a blue organic light emitting device.

According to an exemplary embodiment of the present specification, the light emitting layer includes two or more types of mixed hosts, and one or more of the two or more types of mixed hosts includes the compound represented by Formula 2.

According to an exemplary embodiment of the present specification, the light-emitting layer includes two or more types of mixed hosts, and at least one of the two or more types of mixed hosts includes a compound represented by Formula 2, and the remainder includes deuterium as a substituent. Contains anthracene-based compounds not included.

According to an exemplary embodiment of the present specification, the light-emitting layer includes two or more types of mixed hosts, and at least one of the two or more types of mixed hosts includes a compound represented by Formula 2, and the remainder includes deuterium as a substituent. and an anthracene-based compound different from Formula 2 above.

According to an exemplary embodiment of the present specification, the light-emitting layer includes two or more types of mixed hosts, and at least one of the two or more types of mixed hosts includes a compound represented by Formula 2, and the remainder includes deuterium as a substituent. It includes at least one selected from anthracene-based compounds that do not contain deuterium as a substituent and are different from Formula 2 above.

As long as at least one of the two or more mixed hosts contains the compound represented by Formula 2, and the other is different from Formula 2, any anthracene-based host used in the art can be used without limitation, and is limited to this. It doesn't work.

An organic light emitting device using two or more types of mixed hosts according to an embodiment of the present specification is intended to improve the performance of the device by mixing the advantages of each host. For example, when two types of hosts are mixed, high efficiency And by mixing one type of host with a low-voltage effect and one type of host with a long-life effect, an organic light-emitting device with high efficiency, low voltage, and long lifespan effects can be produced.

According to an exemplary embodiment of the present specification, the organic light emitting device has a maximum emission wavelength (λ _max ) of the emission spectrum of 400 nm to 470 nm.

According to an exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant.

According to an exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

The pyrene-based compounds and non-pyrene-based compounds can be used without limitation as long as they are compounds used in the art, and are not limited thereto.

According to an exemplary embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

According to an exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by Formula 2, and the dopant is one or more selected from a pyrene-based compound and a non-pyrene-based compound. Includes.

According to an exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the light-emitting layer includes host:dopant at a weight ratio of 0.1:99.9 to 20:80.

According to an exemplary embodiment of the present specification, the organic light-emitting device includes an electron transport region provided between the cathode and the light-emitting layer.

According to an exemplary embodiment of the present specification, the organic light-emitting device includes an electron transport region provided between the cathode and the light-emitting layer, and the electron transport region includes a compound represented by the following formula (3).

[Formula 3]

In Formula 3,

X1 is N or Q101, X2 is N or Q102, X3 is N or Q103,

At least one of X1 to X3 is N,

Q101 to Q103 and Q1 to Q3 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; Cyano group; nitro group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, the electron transport region can be used without limitation as long as it is a monocyclic 6-membered heterocyclic compound, that is, a triazine-based derivative, a pyrimidine-based derivative, and a pyridine-based derivative, but is not limited thereto.

According to an exemplary embodiment of the present specification, the electron transport region includes a compound represented by Formula 3, an organic alkali metal complex, and a mixture thereof. At this time, the organic alkali metal complex may include, but is not limited to, lithium quinolate and aluminum quinolate, and the content of the organic alkali metal complex is 10 to 90 wt%, preferably 30 to 70 wt, relative to the material of the organic layer. Included in %.

According to an exemplary embodiment of the present specification, the electron transport region includes an electron transport layer and an electron control layer.

According to an exemplary embodiment of the present specification, the organic light-emitting device may include only the above-described hole transport region and the above-described light-emitting layer as an organic material layer, but may further include an additional organic material layer. For example, it may further include an additional hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.

According to an exemplary embodiment of the present specification, the organic light emitting device may further include an additional organic material layer. The additional organic material layer is one or more layers among a light emitting layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron control layer, an electron blocking layer, a hole blocking layer and a hole control layer. You can have However, the structure of the organic light emitting device is not limited to this and may include a smaller number of organic layers.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic light-emitting device of the present specification is known in the art, except that the layer adjacent to the light-emitting layer among the organic material layers includes the compound represented by Formula 1, and the light-emitting layer includes the compound represented by Formula 2. It can be manufactured using materials and methods.

For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. It can be manufactured by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited to this.

The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : A combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al and Mg/Ag, but they are not limited to these.

A capping layer may be additionally formed on the cathode to protect the electrode, and the capping layer material may be any material used in the art.

The hole injection layer is a hole injection material that injects holes from the electrode, and the hole injection material has the ability to transport holes, so it has an excellent hole injection effect at the anode and a light-emitting layer or light-emitting material. , A compound that prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material and also has excellent thin film forming ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. These include organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and has high mobility for holes. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer. It is a layer that can improve the lifespan and efficiency of the device by using known materials. It can be formed in an appropriate part in between.

The light-emitting material of the light-emitting layer is a material that can emit light in the visible light range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively. The organic light-emitting device of the present specification includes the compound represented by Formula 2 above. When an additional light-emitting layer is included in addition to the light-emitting layer, a material with good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heteroring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heteroring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

An electron control layer may be additionally provided between the light emitting layer and the electron transport layer. The electron control layer material may be any material used in the art.

The electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light-emitting layer, and the electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer. Materials with high mobility are suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect to the light-emitting layer or light-emitting material, and injects holes of excitons generated in the light-emitting layer. A compound that prevents movement to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

The organic light emitting device according to the present specification may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

The structure according to an exemplary embodiment of the present specification may operate on a similar principle to that applied to organic light-emitting devices in organic electronic devices including organic solar cells, organic photoreceptors, and organic transistors.

Manufacturing of the organic light emitting device will be described in detail in the following examples. However, the following examples are for illustrating the present specification, and the scope of the present specification is not limited thereto.

Preparation Example (Synthesis of BH)

The reactant (1eq) and trifluoromethanesulfonic acid (cat.) were added to C ₆ D ₆ (mass ratio 10 to 50 times that of the reactant) and stirred at 70°C for 10 to 100 minutes. After completion of the reaction, D ₂ O (excess) was added and stirred for 30 minutes, and then trimethylamine (excess) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried with MgSO ₄ and recrystallized by heating with toluene to obtain the products shown in Tables 1 and 2 below.

practice
heavy hydrogen
compound reactant product reactant
m/z product
theory
max m/z reaction
hour
(min) product
real
max m/z entire
number of hydrogen D substitution
Count D substitution
ratio (%) synthesis
yield
(%) Compound 1-1 520 544 30 538 24 18 75% 70% Compound 1-2 496 520 30 513 24 17 71% 73% Compound 1-3 496 520 50 520 24 24 100% 74% compound
1-4 546 572 15 560 26 14 54% 69% Compound 1-5 496 519 25 510 23 14 61% 70% Compound 1-6 420 440 35 438 20 18 90% 73% Compound 1-7 570 595 40 591 25 21 84% 71% Compound 1-8 546 572 10 558 26 12 46% 68% Compound 1-9 572 600 60 596 28 24 86% 65% Compound 1-10 470 492 50 492 22 22 100% 66% Compound 1-11 596 624 55 620 28 24 86% 72% Compound 1-12 572 600 40 593 28 21 75% 71% Compound 1-13 546 572 75 572 26 26 100% 73% Compound 1-14 496 520 60 519 24 23 96% 65% Compound 1-15 546 572 60 568 26 22 85% 66% Compound 1-16 496 520 50 518 24 22 92% 70% Compound 1-17 510 532 20 525 22 15 68% 68% Compound 1-18 510 532 30 528 22 18 82% 64% Compound 1-19 510 532 40 531 22 21 95% 68% Compound 1-20 470 492 60 492 22 22 100% 70% Compound 1-21 546 572 30 569 26 23 88% 69% Compound 1-22 648 680 50 677 32 29 91% 72% Compound 1-23 622 652 50 648 30 26 87% 73% Compound 1-24 622 652 60 648 30 26 87% 80% Compound 1-25 546 572 50 568 26 22 85% 71% Compound 1-26 622 652 70 650 30 28 93% 73% Compound 1-27 572 599 60 598 27 26 96% 72%

Each product had different degrees of deuterium substitution depending on the reaction time, and the substitution rate was determined based on the maximum m/z (M+) value.

The reactant was synthesized by referring to the company's prior literature such as KR1964435, KR1899728, KR1975945, KR2018-0098122, KR2018-0102937, and KR2018-0103352. In addition, for deuterium substitution of the above product, the prior literature of KR1538534 was referred to.

practice
heavy hydrogen
compound reactant product reactant
m/z product
theory
max m/z reaction
hour
(min) product
real
max m/z entire
number of hydrogen D substitution
Count D substitution
ratio (%) synthesis
yield
(%) Compound 2-1 470 492 50 490 22 20 91% 65% Compound 2-2 470 492 30 486 22 16 73% 70% Compound 2-3 546 572 50 569 26 23 88% 71% Compound 2-4 570 596 30 590 26 20 77% 65% Compound 2-5 470 492 40 489 22 19 86% 66% Compound 2-6 622 652 50 649 30 27 90% 71% Compound 2-7 546 572 35 567 26 21 81% 70% Compound 2-8 596 624 40 619 28 23 82% 75% Compound 2-9 520 544 60 543 24 23 96% 69% Compound 2-10 570 596 60 594 26 24 92% 68% Compound 2-11 520 544 35 538 24 18 75% 63% Compound 2-12 510 532 60 531 22 21 95% 66% Compound 2-13 560 584 15 572 24 12 50% 65% Compound 2-14 586 612 40 607 26 21 81% 67% Compound 2-15 560 584 75 584 24 24 100% 70% Compound 2-16 586 612 60 610 26 24 92% 70% Compound 2-17 560 584 60 580 24 20 83% 69% Compound 2-18 586 612 50 607 26 21 81% 75% Compound 2-19 546 572 60 568 26 22 85% 72% Compound 2-20 596 624 60 620 28 24 86% 70%

Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate was determined according to the maximum m/z (M+) value. The reactants are described in our prior literature such as KR 1994238 B1, KR 1670193 B1, KR1754445 B1, and KR 1368164 B1. It was synthesized with reference to . In addition, for deuterium substitution of the above product, reference was made to the prior literature of KR 1538534 B1.

In addition, referring to the above prior literature, compounds 1-21 to 1-22 and BH3 (deuterium substitution rate 0%), BH4 (deuterium substitution rate 25%), and BH5 (deuterium substitution rate 35%) have deuterium substitution rates of 40% and 65%, respectively. was synthesized and a comparative experiment with compounds with different deuterium substitution rates was also performed.

Each product had different degrees of deuterium substitution depending on the reaction time, and the substitution rate was determined based on the maximum m/z (M+) value.

The reactant was synthesized by referring to the company's prior literature such as KR 1994238 B1, KR 1670193 B1, KR1754445 B1, and KR 1368164 B1. In addition, for deuterium substitution of the above product, reference was made to the prior literature of KR 1538534 B1.

In addition, referring to the above prior literature, compounds 1-21 to 1-22 and BH3 (deuterium substitution rate 0%), BH4 (deuterium substitution rate 25%), and BH5 (deuterium substitution rate 35%) have deuterium substitution rates of 40% and 65%, respectively. was synthesized and a comparative experiment with compounds with different deuterium substitution rates was also performed.

The products of Tables 1 and 2, compounds 1-21 and 1-22 are disclosed in JP 4070676 B2, KR 1477844 B1, US 6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082 B2, JP 5015459 B2, KR 1979037. B1, KR It was synthesized by referring to prior literature such as 1550351 B1, KR 1503766 B1, KR 0826364 B1, KR 0749631 B1, and KR 1115255 B1. In addition, deuterium (-D) bound to the products synthesized in Tables 1 and 2 above means that it can be bound to the indicated position, and does not necessarily mean that it must be bound to the indicated position.

In addition, compounds 3-1 to 3-18, which are compounds represented by Formula 1 included in the hole transport region below, were synthesized with reference to JP 2015-530364 A, US 5840217 A, WO2013-120577 A, KR 2016-0035610 A. did.

<Comparative Example 1-1> Manufacturing of organic light emitting device

As an anode, a substrate on which 70/1000/70Å ITO/Ag/ITO was deposited was cut into 50 mm × 50 mm × 0.5 mm, placed in distilled water with a dispersant dissolved in it, and washed ultrasonically. Detergent was used from Fischer Co., and distilled water was from Millipore Co. Distilled water that was filtered secondarily was used as a filter for the product. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed in the order of isopropyl alcohol, acetone, and methanol and dried.

On the anode prepared in this way, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a hole transport material, was vacuum deposited to a thickness of 1150 Å on top of it to form a hole transport layer. Next, a hole control layer was formed using EB1 (150 Å), and then BH1 and dopant BD1 (2% by weight) were vacuum deposited to a thickness of 360 Å to form a light emitting layer. Afterwards, 50Å of HB1 was deposited to form an electron control layer, and compounds ET1 and Liq were mixed at a 5:5 (mass ratio) to form an electron transport layer with a thickness of 250Å. Magnesium and lithium fluoride (LiF) with a thickness of 50 Å were sequentially formed as an electron injection layer <EIL>, and then 200 Å of magnesium and silver (1:4) were formed as a cathode, and then 600 Å of CP1 was deposited to complete the device. In the above process, the deposition rate of organic matter was maintained at 1 Å/sec.

<Comparative Examples 1-2 to 1-15 and Examples 1-1 to 1-43>

In Comparative Example 1-1, the compounds in Table 3 below were used instead of BH1 as the host of the light emitting layer, and the compounds in Table 3 below were used instead of EB1 as the hole control layer. Same as Comparative Example 1-1. Organic light-emitting devices were manufactured, and the structures of the organic light-emitting devices manufactured in Comparative Examples 1-1 to 1-15 and Examples 1-1 to 1-43 are shown in Table 3 below, and Table 4 below shows the comparison These are the results of measuring the driving voltage, luminous efficiency, and time to reach 95% of the initial luminance (LT95) for Examples 1-1 to 1-15 and Examples 1-1 to 1-43 at a current density of 20 mA/cm ^2. .

# Hole transport area luminescent layer Electronic transport area hole transport layer Hole control layer host dopant Electronic control layer electron transport layer Comparative Example 1-1 HT1 EB1 BH1 BD1 HB1 ET1 Comparative Example 1-2 HT1 EB2 BH1 BD1 HB1 ET1 Comparative Example 1-3 HT1 EB3 BH1 BD1 HB1 ET1 Comparative Example 1-4 HT1 EB1 BH2 BD1 HB1 ET1 Comparative Example 1-5 HT1 EB2 BH2 BD1 HB1 ET2 Comparative Example 1-6 HT1 EB1 BH1:BH2(1:1) BD1 HB1 ET1 Comparative Example 1-7 HT1 Compound 3-1 BH1 BD1 HB1 ET1 Comparative Example 1-8 HT1 Compound 3-10 BH2 BD1 HB1 ET1 Comparative Example 1-9 HT1 EB1 Compound 1-1 BD1 HB1 ET1 Comparative Example 1-10 HT1 EB1 Compound 2-3 BD1 HB1 ET1 Comparative Example 1-11 HT1 EB1 BH3 BD1 HB1 ET1 Comparative Example 1-12 HT1 EB1 BH4 BD1 HB1 ET1 Comparative Example 1-13 HT1 EB1 BH5 BD1 HB1 ET1 Comparative Example 1-14 HT1 Compound 3-13 BH3 BD1 HB1 ET1 Comparative Example 1-15 HT1 Compound 3-13 BH4 BD1 HB1 ET1 Example 1-1 HT1 Compound 3-1 Compound 1-1 BD1 HB1 ET1 Example 1-2 HT1 Compound 3-1 Compound 1-2 BD1 HB1 ET1 Example 1-3 HT1 Compound 3-2 Compound 1-3 BD1 HB1 ET1 Example 1-4 HT1 Compound 3-2 Compound 1-4 BD1 HB1 ET1 Example 1-5 HT1 Compound 3-3 Compound 1-5 BD1 HB1 ET1 Example 1-6 HT1 Compound 3-3 Compound 1-6 BD1 HB1 ET1 Example 1-7 HT1 Compound 3-4 Compound 1-7 BD1 HB1 ET1 Example 1-8 HT1 Compound 3-4 Compound 1-8 BD1 HB1 ET1 Example 1-9 HT1 Compound 3-5 Compound 1-9 BD1 HB1 ET1 Example 1-10 HT1 Compound 3-5 Compound 1-10 BD1 HB1 ET1 Example 1-11 HT1 Compound 3-6 Compound 1-11 BD1 HB1 ET1 Example 1-12 HT1 Compound 3-6 Compound 1-12 BD1 HB1 ET1 Example 1-13 HT1 Compound 3-7 Compound 1-13 BD1 HB1 ET1 Example 1-14 HT1 Compound 3-7 Compound 1-14 BD1 HB1 ET1 Example 1-15 HT1 Compound 3-8 Compound 1-15 BD1 HB1 ET1 Example 1-16 HT1 Compound 3-8 Compound 1-16 BD1 HB1 ET1 Example 1-17 HT1 Compound 3-9 Compound 1-17 BD1 HB1 ET1 Example 1-18 HT1 Compound 3-9 Compound 1-18 BD1 HB1 ET1 Example 1-19 HT1 Compound 3-10 Compound 1-19 BD1 HB1 ET1 Example 1-20 HT1 Compound 3-10 Compound 1-20 BD1 HB1 ET1 Example 1-21 HT1 Compound 3-11 Compound 1-21 BD1 HB1 ET1 Example 1-22 HT1 Compound 3-11 Compound 1-24 BD1 HB1 ET1 Example 1-23 HT1 Compound 3-12 Compound 1-27 BD1 HB1 ET1 Example 1-24 HT1 Compound 3-12 Compound 2-1 BD1 HB1 ET1 Example 1-25 HT1 Compound 3-13 Compound 2-2 BD1 HB1 ET1 Example 1-26 HT1 Compound 3-13 Compound 2-3 BD1 HB1 ET1 Example 1-27 HT1 Compound 3-14 Compound 2-4 BD1 HB1 ET1 Example 1-28 HT1 Compound 3-14 Compound 2-5 BD1 HB1 ET1 Example 1-29 HT1 Compound 3-15 Compound 2-6 BD1 HB1 ET1 Example 1-30 HT1 Compound 3-15 Compound 2-7 BD1 HB1 ET1 Example 1-31 HT1 Compound 3-16 Compound 2-8 BD1 HB1 ET1 Example 1-32 HT1 Compound 3-16 Compound 2-9 BD1 HB1 ET1 Example 1-33 HT1 Compound 3-17 Compound 2-10 BD1 HB1 ET1 Example 1-34 HT1 Compound 3-17 Compound 2-11 BD1 HB1 ET1 Example 1-35 HT1 Compound 3-18 Compound 2-14 BD1 HB1 ET1 Example 1-36 HT1 Compound 3-18 Compound 2-17 BD1 HB1 ET1 Example 1-37 HT1 Compound 3-3 Compound 2-18 BD1 HB1 ET1 Example 1-38 HT1 Compound 3-14 Compound 2-19 BD1 HB1 ET1 Example 1-39 HT1 Compound 3-1 Compound 1-1: Compound 1-20 (1:1) BD1 HB1 ET1 Example 1-40 HT1 Compound 3-14 Compound 1-3: Compound 2-2 (1:1) BD1 HB1 ET1 Example 1-41 HT1 Compound 3-17 Compound 1-13: Compound 2-10 (1:1) BD1 HB1 ET1 Example 1-42 HT1 Compound 3-13 Compound 1-21 BD1 HB1 ET1 Example 1-43 HT1 Compound 3-18 Compound 1-22 BD1 HB1 ET1

#
20 mA/㎠ Device results Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) Color coordinates
(x,y) life span
(T95,h)
(@20mA/cm ² ) Comparative Example 1-1 4.44 4.89 (0.135, 0.131) 40.1 Comparative Example 1-2 4.38 4.58 (0.135, 0.138) 50.3 Comparative Example 1-3 4.40 4.60 (0.135, 0.136) 45.8 Comparative Example 1-4 4.50 4.50 (0.135, 0.135) 42.1 Comparative Example 1-5 4.78 4.66 (0.135, 0.136) 30.2 Comparative Example 1-6 4.33 4.90 (0.135, 0.138) 60.1 Comparative Example 1-7 4.28 4.70 (0.135, 0.133) 43.9 Comparative Example 1-8 4.25 4.61 (0.135, 0.138) 40.5 Comparative Example 1-9 4.23 4.82 (0.135, 0.138) 65.1 Comparative Example 1-10 4.33 4.77 (0.135, 0.138) 63.4 Comparative Example 1-11 4.12 5.32 (0.135, 0.138) 49.3 Comparative Example 1-12 4.20 5.08 (0.135, 0.138) 51.1 Comparative Example 1-13 4.09 4.99 (0.135, 0.138) 50.8 Comparative Example 1-14 4.10 5.20 (0.135, 0138) 40.3 Comparative Example 1-15 4.11 5.10 (0.135, 0138) 48.5 Example 1-1 3.70 5.68 (0.135, 0.138) 72.5 Example 1-2 3.81 5.72 (0.135, 0.138) 73.5 Example 1-3 3.65 5.84 (0.135, 0.138) 70.5 Example 1-4 3.73 5.79 (0.135, 0.138) 80.2 Example 1-5 3.80 5.70 (0.135, 0.138) 75.1 Example 1-6 3.75 5.80 (0.135, 0.138) 72.9 Example 1-7 3.66 5.81 (0.135, 0.138) 74.1 Example 1-8 3.71 5.78 (0.135, 0.138) 76.7 Example 1-9 3.64 5.64 (0.135, 0.138) 79.5 Example 1-10 3.74 5.84 (0.135, 0.138) 69.9 Example 1-11 3.77 5.88 (0.135, 0.137) 70.5 Example 1-12 3.66 5.66 (0.135, 0.138) 73.5 Example 1-13 3.61 5.61 (0.135, 0.132) 74.5 Example 1-14 3.73 5.67 (0.135, 0.131) 80.1 Example 1-15 3.71 5.81 (0.135, 0.138) 78.5 Example 1-16 3.68 5.69 (0.135, 0.140) 77.7 Example 1-17 3.55 5.70 (0.135, 0.138) 74.3 Example 1-18 3.48 5.71 (0.135, 0.138) 76.2 Example 1-19 3.51 5.80 (0.135, 0.138) 77.8 Example 1-20 3.62 5.95 (0.135, 0.138) 71.5 Example 1-21 3.65 5.99 (0.135, 0.138) 74.6 Example 1-22 3.70 5.99 (0.135, 0.144) 79.2 Example 1-23 3.77 5.95 (0.135, 0.145) 77.4 Example 1-24 3.60 5.81 (0.135, 0.138) 75.2 Example 1-25 3.68 5.78 (0.135, 0.139) 74.2 Example 1-26 3.66 5.70 (0.135, 0.136) 73.8 Example 1-27 3.67 5.68 (0.135, 0.139) 70.6 Example 1-28 3.70 5.81 (0.135, 0.138) 69.0 Example 1-29 3.59 5.88 (0.135, 0.138) 70.2 Example 1-30 3.71 5.69 (0.135, 0.139) 68.1 Example 1-31 3.64 5.80 (0.135, 0.139) 72.1 Example 1-32 3.57 5.77 (0.135, 0.138) 73.3 Example 1-33 3.63 5.83 (0.135, 0.139) 74.2 Example 1-34 3.69 5.91 (0.135, 0.138) 75.6 Example 1-35 3.71 5.81 (0.135, 0.139) 77.1 Example 1-36 3.61 5.76 (0.135, 0.139) 68.9 Example 1-37 3.66 5.97 (0.135, 0.145) 74.8 Example 1-38 3.60 6.00 (0.135, 0.143) 75.1 Example 1-39 3.54 6.01 (0.135, 0.136) 80.1 Example 1-40 3.55 6.03 (0.135, 0.140) 82.1 Example 1-41 3.51 6.12 (0.135, 0.139) 79.5 Example 1-42 3.75 5.81 (0.135, 0.138) 70.3 Example 1-43 3.76 5.80 (0.135, 0.138) 71.0

In Tables 3 and 4, the organic light-emitting device according to an embodiment of the present specification has a light-emitting layer by using a compound of Formula 1 applied to the hole transport region of the blue organic electroluminescent device and a compound of Formula 2 applied as a host of the light-emitting layer. showed excellent hole injection and transport abilities. In addition, through the balance of holes and electrons in the organic light-emitting device according to the chemical structure, the organic light-emitting device according to the present specification exhibits superior characteristics in terms of efficiency, driving voltage, and stability than the organic light-emitting device containing Formula 1 or Formula 2, respectively. It was.

In particular, the results of device characteristics according to the deuterium substitution rate of Formula 2 can also be observed by looking at the results in Tables 3 and 4. Comparative Examples 1-11 to 1-13 using compounds having a deuterium substitution rate of unsubstituted (0%), 20%, and 35%, respectively, of Compound 1-6, Example 1- using a compound having a deuterium substitution rate of 40% or more It shows a significantly lower lifespan compared to 6, 1-42 and 1-43, and it can be seen that the effect of increasing lifespan due to deuterium substitution is minimal. On the other hand, Examples 1-6, 1-42, and 1-43, in which the deuterium substitution rate of Formula 2 is 40% or more, significantly improved the lifespan of the device compared to Comparative Examples 1-11 to 1-13, and the deuterium substitution rate of Formula 2 It can be seen that the lifespan of the device is greatly improved when it is 40% or more.

In addition, when comparing Examples 1-42 and 1-43 with Comparative Examples 1-14 and 1-15, the lifespan of Examples 1-42 and 1-43 having a deuterium substitution rate of Formula 2 of 40% or more was significantly increased. It can be seen that the efficiency and driving voltage are also improved.

<Comparative Example 2-1> Manufacturing of organic light emitting device

As an anode, a substrate on which 70/1000/70Å ITO/Ag/ITO was deposited was cut into 50 mm × 50 mm × 0.5 mm, placed in distilled water with a dispersant dissolved in it, and washed ultrasonically. Detergent was used from Fischer Co., and distilled water was from Millipore Co. Distilled water that was filtered secondarily was used as a filter for the product. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed in the order of isopropyl alcohol, acetone, and methanol and dried.

On the anode prepared in this way, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a hole transport material, was vacuum deposited to a thickness of 1150 Å on top of it to form a hole transport layer. Next, a hole control layer was formed using EB1 (150Å), and then BH1 and dopant BD2 (2% by weight) were vacuum deposited to a thickness of 360Å to form a light emitting layer. Afterwards, 50Å of HB1 was deposited to form an electron control layer, and compounds ET1 and Liq were mixed at a 5:5 (mass ratio) to form an electron transport layer with a thickness of 250Å. Magnesium and lithium fluoride (LiF) with a thickness of 50 Å were sequentially formed as an electron injection layer <EIL>, and then 200 Å of magnesium and silver (1:4) were formed as a cathode, and then 600 Å of CP1 was deposited to complete the device. In the above process, the deposition rate of organic matter was maintained at 1 Å/sec.

<Comparative Examples 2-2 to 2-10 and Examples 2-1 to 2-41>

In Comparative Example 2-1, the compounds in Table 5 below were used instead of BH1 as the host of the light emitting layer, and the compounds in Table 5 below were used instead of EB1 as the hole control layer. Same as Comparative Example 2-1. Organic light-emitting devices were manufactured, and the structures of the organic light-emitting devices manufactured in Comparative Examples 2-1 to 2-10 and Examples 2-1 to 2-41 are shown in Table 5 below, and Table 6 below shows the comparison. These are the results of measuring the driving voltage, luminous efficiency, and time to reach 95% of the initial luminance (LT95) for Examples 2-1 to 2-10 and Examples 2-1 to 2-41 at a current density of 20 mA/cm ^2. .

# Hole transport area luminescent layer Electronic transport area hole transport layer Hole control layer host dopant Electronic control layer electron transport layer Comparative Example 2-1 HT1 EB1 BH1 BD2 HB1 ET1 Comparative Example 2-2 HT1 EB2 BH1 BD2 HB1 ET1 Comparative Example 2-3 HT1 EB3 BH1 BD2 HB1 ET1 Comparative Example 2-4 HT1 EB1 BH2 BD2 HB1 ET1 Comparative Example 2-5 HT1 EB2 BH2 BD2 HB1 ET2 Comparative Example 2-6 HT1 EB1 BH1:BH2(1:1) BD2 HB1 ET1 Comparative Example 2-7 HT1 Compound 3-1 BH1 BD2 HB1 ET1 Comparative Example 2-8 HT1 Compound 3-10 BH2 BD2 HB1 ET1 Comparative Example 2-9 HT1 EB1 Compound 1-1 BD2 HB1 ET1 Comparative Example 2-10 HT1 EB1 Compound 2-3 BD2 HB1 ET1 Example 2-1 HT1 Compound 3-1 Compound 1-1 BD2 HB1 ET1 Example 2-2 HT1 Compound 3-1 Compound 1-2 BD2 HB1 ET1 Example 2-3 HT1 Compound 3-2 Compound 1-3 BD2 HB1 ET1 Example 2-4 HT1 Compound 3-2 Compound 1-4 BD2 HB1 ET1 Example 2-5 HT1 Compound 3-3 Compound 1-5 BD2 HB1 ET1 Example 2-6 HT1 Compound 3-3 Compound 1-6 BD2 HB1 ET1 Example 2-7 HT1 Compound 3-4 Compound 1-7 BD2 HB1 ET1 Example 2-8 HT1 Compound 3-4 Compound 1-8 BD2 HB1 ET1 Example 2-9 HT1 Compound 3-5 Compound 1-9 BD2 HB1 ET1 Example 2-10 HT1 Compound 3-5 Compound 1-10 BD2 HB1 ET1 Example 2-11 HT1 Compound 3-6 Compound 1-11 BD2 HB1 ET1 Example 2-12 HT1 Compound 3-6 Compound 1-12 BD2 HB1 ET1 Example 2-13 HT1 Compound 3-7 Compound 1-13 BD2 HB1 ET1 Example 2-14 HT1 Compound 3-7 Compound 1-14 BD2 HB1 ET1 Example 2-15 HT1 Compound 3-8 Compound 1-15 BD2 HB1 ET1 Example 2-16 HT1 Compound 3-8 Compound 1-16 BD2 HB1 ET1 Example 2-17 HT1 Compound 3-9 Compound 1-17 BD2 HB1 ET1 Example 2-18 HT1 Compound 3-9 Compound 1-18 BD2 HB1 ET1 Example 2-19 HT1 Compound 3-10 Compound 1-19 BD2 HB1 ET1 Example 2-20 HT1 Compound 3-10 Compound 1-22 BD2 HB1 ET1 Example 2-21 HT1 Compound 3-11 Compound 1-23 BD2 HB1 ET1 Example 2-22 HT1 Compound 3-11 Compound 1-25 BD2 HB1 ET1 Example 2-23 HT1 Compound 3-12 Compound 1-26 BD2 HB1 ET1 Example 2-24 HT1 Compound 3-12 Compound 2-1 BD2 HB1 ET1 Example 2-25 HT1 Compound 3-13 Compound 2-2 BD2 HB1 ET1 Example 2-26 HT1 Compound 3-13 Compound 2-3 BD2 HB1 ET1 Example 2-27 HT1 Compound 3-14 Compound 2-4 BD2 HB1 ET1 Example 2-28 HT1 Compound 3-14 Compound 2-5 BD2 HB1 ET1 Example 2-29 HT1 Compound 3-15 Compound 2-6 BD2 HB1 ET1 Example 2-30 HT1 Compound 3-15 Compound 2-7 BD2 HB1 ET1 Example 2-31 HT1 Compound 3-16 Compound 2-8 BD2 HB1 ET1 Example 2-32 HT1 Compound 3-16 Compound 2-9 BD2 HB1 ET1 Example 2-33 HT1 Compound 3-17 Compound 2-12 BD2 HB1 ET1 Example 2-34 HT1 Compound 3-17 Compound 2-13 BD2 HB1 ET1 Example 2-35 HT1 Compound 3-18 Compound 2-15 BD2 HB1 ET1 Example 2-36 HT1 Compound 3-18 Compound 2-16 BD2 HB1 ET1 Example 2-37 HT1 Compound 3-9 Compound 2-18 BD2 HB1 ET1 Example 2-38 HT1 Compound 3-17 Compound 2-20 BD2 HB1 ET1 Example 2-39 HT1 Compound 3-1 Compound 1-8: Compound 1-20 (1:1) BD2 HB1 ET1 Example 2-40 HT1 Compound 3-14 Compound 1-4: Compound 2-8 (1:1) BD2 HB1 ET1 Example 2-41 HT1 Compound 3-17 Compound 1-11: Compound 2-12 (1:1) BD2 HB1 ET1

#
20 mA/㎠ Device results Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) Color coordinates
(x,y) life span
(T95,h)
(@20mA/cm ² ) Comparative Example 2-1 4.45 4.80 (0.136, 0.120) 30.1 Comparative Example 2-2 4.40 4.60 (0.136, 0.120) 40.2 Comparative Example 2-3 4.41 4.61 (0.136, 0.120) 33.4 Comparative Example 2-4 4.49 4.51 (0.136, 0.120) 31.8 Comparative Example 2-5 4.80 4.70 (0.136, 0.120) 21.5 Comparative Example 2-6 4.32 4.90 (0.136, 0.120) 48.9 Comparative Example 2-7 4.29 4.71 (0.136, 0.120) 31.0 Comparative Example 2-8 4.26 4.72 (0.136, 0.120) 28.1 Comparative Example 2-9 4.25 4.80 (0.136, 0.120) 48.5 Comparative Example 2-10 4.32 4.76 (0.136, 0.121) 45.5 Example 2-1 3.68 6.01 (0.136, 0.120) 60.5 Example 2-2 3.70 6.12 (0.136, 0.120) 61.2 Example 2-3 3.58 6.03 (0.136, 0.120) 63.5 Example 2-4 3.66 6.55 (0.136, 0.120) 70.2 Example 2-5 3.71 5.99 (0.136, 0.120) 64.5 Example 2-6 3.65 6.20 (0.136, 0.120) 66.2 Example 2-7 3.61 6.11 (0.136, 0.120) 63.1 Example 2-8 3.6 5.98 (0.136, 0.120) 65.1 Example 2-9 3.55 5.9 (0.136, 0.120) 70.5 Example 2-10 3.68 6.11 (0.136, 0.120) 64.1 Example 2-11 3.69 6.19 (0.136, 0.120) 60.4 Example 2-12 3.51 6.08 (0.136, 0.120) 65.4 Example 2-13 3.54 5.89 (0.136, 0.120) 68.4 Example 2-14 3.60 5.93 (0.136, 0.120) 70.5 Example 2-15 3.64 6.11 (0.136, 0.120) 79.4 Example 2-16 3.55 5.83 (0.136, 0.120) 61.5 Example 2-17 3.46 5.94 (0.136, 0.120) 63.5 Example 2-18 3.40 6.00 (0.136, 0.120) 64.8 Example 2-19 3.41 6.02 (0.136, 0.120) 70.1 Example 2-20 3.50 6.23 (0.136, 0.120) 65.2 Example 2-21 3.60 6.25 (0.136, 0.120) 66.8 Example 2-22 3.61 6.31 (0.136, 0.123) 69.4 Example 2-23 3.63 6.30 (0.136, 0.124) 69.1 Example 2-24 3.58 6.05 (0.136, 0.120) 67.4 Example 2-25 3.46 6.00 (0.136, 0.120) 66.5 Example 2-26 3.48 5.98 (0.136, 0.120) 68.3 Example 2-27 3.59 5.98 (0.136, 0.120) 61.2 Example 2-28 3.62 6.10 (0.136, 0.120) 63.2 Example 2-29 3.51 6.11 (0.136, 0.120) 63.4 Example 2-30 3.63 5.90 (0.136, 0.120) 60.5 Example 2-31 3.51 6.13 (0.136, 0.120) 66.8 Example 2-32 3.49 6.02 (0.136, 0.120) 64.2 Example 2-33 3.58 6.10 (0.136, 0.120) 66.5 Example 2-34 3.61 6.23 (0.136, 0.120) 67.2 Example 2-35 3.60 6.05 (0.136, 0.120) 69.5 Example 2-36 3.52 5.94 (0.136, 0.120) 60.5 Example 2-37 3.55 6.23 (0.136, 0.125) 66.4 Example 2-38 3.48 6.28 (0.136, 0.124) 67.5 Example 2-39 3.55 6.33 (0.136, 0.120) 72.5 Example 2-40 3.49 6.35 (0.136, 0.120) 73.8 Example 2-41 3.40 6.40 (0.136, 0.120) 75.1

In Tables 3 to 6, the organic light-emitting device according to an embodiment of the present specification has a light-emitting layer by using a compound of Formula 1 applied to the hole transport region of the blue organic electroluminescent device and Formula 2 applied as a host of the light-emitting layer. showed excellent hole injection and transport abilities. In addition, through the balance of holes and electrons in the organic light-emitting device according to the chemical structure, the organic light-emitting device according to the present specification exhibits superior characteristics in terms of efficiency, driving voltage, and stability than the organic light-emitting device containing Formula 1 or Formula 2, respectively. It was.

Examples 1-1 to 1-38, 1-42, 1-43, and 2-1 to 2-38 used the compound of Formula 1 as a hole transport layer and the compound of Formula 2 as the host of the light emitting layer. The device was manufactured. The configuration of the device shows that various hole control layers corresponding to Formula 1, various blue hosts corresponding to Formula 2, and BD1 or BD2 among blue fluorescent dopants can be applied. Additionally, Examples 1-39 to 1-41 and 2-39 to 2-41 show that the performance of the device can be improved by using two types of hosts corresponding to Formula 2 as a mixed host.

Comparative Examples 1-1 to 1-6, 1-11 to 1-13, and 2-1 to 2-6 are the results of devices manufactured with a compound other than the combination of compounds 1 and 2 according to an embodiment of the present specification. And the host of the light-emitting layer was an aryl-based anthracene. In all cases, high voltage, low efficiency, and low lifespan indicate low device performance.

Comparative Examples 1-7, 1-8, 1-14, 1-15, 2-7, and 2-8 are the results of applying only the hole control layer corresponding to Formula 1, and Comparative Examples 1-1 to 1-6, A slight tendency to decrease the driving voltage compared to 1-11 to 1-13 and 2-1 to 2-6 can be observed, but it can be seen that the overall device performance is not improved. In addition, Comparative Examples 1-9, 1-10, 2-9, and 2-10 are the results of applying only the blue host corresponding to Formula 2, and Comparative Examples 1-1 to 1-6, 1-11 to 1- An increase in overall lifespan can be observed compared to 13 and 2-1 to 2-6.

Compared to Comparative Examples 1-1 to 1-15 and 2-1 to 2-10, Examples 1-1 to 1-43 and 2-1 to 2-41 are carriers of devices by a combination of Formulas 1 and 2 of the present specification. , In particular, it is easy for holes to be injected into the host, which plays a role in maintaining the balance of the device and shows that overall improvement in device performance is possible.

Examples 2-1 to 2-41 are the results of devices using a combination of BD2 and Chemical Formulas 1 and 2 of the present specification, and it was observed that the device balance of the combination was excellent even when various types of blue dopants were introduced. can do.

1: substrate
2: anode
3: Hole transport area
4: Light-emitting layer
5: cathode
3-1: Hole transport layer
3-2: Hole control layer
6: Hole injection layer
7: Electron transport area
7-1: Electronic control layer
7-2: Electron transport layer
8: Electron injection layer

Claims (24)

anode;
cathode;
A light emitting layer provided between the anode and the cathode; and
An organic light-emitting device comprising a hole transport region including two or more organic material layers provided between the light-emitting layer and the anode,
Among the organic material layers, the organic material layer in contact with the light-emitting layer includes a compound represented by the following formula 1,
The light-emitting layer is an organic light-emitting device comprising a compound represented by the following formula (2):
[Formula 1]

In Formula 1,
One of R8 and R9 is a group represented by the following formula (a), and among R8 and R9, a group other than the group represented by the formula (a), R1 to R7 and R10 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or a group among R8 and R9 that is not a group represented by the following formula (a), and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring. can form,
[Formula a]

In formula a,
L1 to L3 are the same or different from each other and are each independently directly bonded; 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; halogen group; hydroxyl group; Cyano group; nitro group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
l1 to l3 are each integers from 1 to 3,
When l1 is 2 or more, the 2 or more L1 are the same or different from each other,
When l2 is 2 or more, L2 of 2 or more is the same or different from each other,
When the l3 is 2 or more, the 2 or more L3s are the same or different from each other,
means a site bound to R8 or R9 of Formula 1,
[Formula 2]

In Formula 2,
At least one of G1 to G10 is a group represented by the following formula (b), the others are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; Cyano group; nitro group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
[Formula b]

In formula b,
A and B are the same or different and are substituted or unsubstituted hydrocarbon rings; Or a substituted or unsubstituted heterocycle,
One of A and B is a substituted or unsubstituted hydrocarbon ring of 3 or more rings; Or a substituted or unsubstituted heterocycle,
L4 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
l4 is an integer from 1 to 3,
When l4 is 2 or more, the 2 or more L4 are the same or different from each other,
means a site bound to at least one of G1 to G10 of Formula 2,
The deuterium substitution rate of Formula 2 is 40% to 100%. The organic light-emitting device according to claim 1, wherein the deuterium substitution rate of Formula 2 is 40% to 99%. The organic light-emitting device according to claim 1, wherein the deuterium substitution rate of Formula 1 is 1% to 100%. The method of claim 1, wherein any one of R8 and R9 is a group represented by the formula (a), and among the R8 and R9, groups other than the group represented by the formula (a), R1 to R7 and R10 to R18 are the same as or different from each other. , each independently hydrogen; heavy hydrogen; A straight 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 among R8 and R9 that is not a group represented by the following formula (a), and adjacent groups among R1 to R6, R7, and R10 to R18 are each other. An organic light-emitting device that combines to form a polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms. The method according to claim 1, wherein L1 to L3 are the same or different from each other, and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with one or more selected from deuterium, a straight or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or an organic light emitting device that is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms, substituted or unsubstituted with deuterium, or a straight or branched chain alkyl group having 1 to 30 carbon atoms. The method of claim 1, wherein Ar1 and Ar2 are the same or different from each other, and each independently represents a deuterium, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a straight-chain or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium, or a carbon number. a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with one or more selected from the group consisting of a straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or an organic light-emitting device that is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms and at least one selected from deuterium, a straight or branched chain alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. . The method according to claim 1, wherein at least one of G1 to G10 is a group represented by the following formula (b), and the others are the same or different from each other and are each independently hydrogen; heavy hydrogen; Or an organic light emitting device that is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with one or more selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium. The method according to claim 1, wherein L4 is a direct bond; Or an organic light-emitting device that is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium. The method of claim 1, wherein A and B are the same or different from each other, and are each independently substituted or unsubstituted with one or more selected from deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium. a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms substituted or unsubstituted with deuterium,
One of A and B is a substituted or unsubstituted aromatic hydrocarbon ring of 3 or more rings; Or an organic light-emitting device that is a substituted or unsubstituted heterocycle of three or more rings. The organic light-emitting device according to claim 1, wherein Formula 1 is any one selected from the following compounds:
































The organic light-emitting device according to claim 1, wherein Formula 2 is any one selected from the following compounds:








The organic light-emitting device according to claim 1, wherein the organic material layer in contact with the anode among the organic material layers includes a carbazole-based compound. The organic light-emitting device according to claim 1, wherein the organic material layer includes a hole transport layer and a hole control layer, and the hole transport layer includes a compound represented by Formula 1. The organic light-emitting device according to claim 1, wherein the triplet energy of Formula 1 is 2.4 eV to 2.8 eV. The organic light-emitting device of claim 1, wherein the light-emitting layer includes a host and a dopant, and the host includes a compound represented by Formula 2. The organic light-emitting device of claim 1, wherein the light-emitting layer includes two or more mixed hosts, and at least one of the two or more mixed hosts includes a compound represented by Formula 2. The method of claim 1, wherein the light-emitting layer includes two or more types of mixed hosts, at least one of the two or more types of mixed hosts includes the compound represented by Formula 2, and the remainder is an anthracene-based compound that does not contain deuterium as a substituent. An organic light-emitting device comprising a compound, and at least one anthracene-based compound containing deuterium as a substituent and different from Formula 2 above. The organic light-emitting device according to claim 1, wherein the organic light-emitting device has a maximum emission wavelength (λ _max ) of an emission spectrum of 400 nm to 470 nm. The organic light emitting device of claim 1, wherein the light emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant. The organic light-emitting device of claim 1, wherein the light-emitting layer includes a host and a dopant, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound. The organic light emitting device of claim 20, wherein the non-pyrene-based compound includes a boron-based compound. The organic light emitting device of claim 1, wherein the organic light emitting device includes an electron transport region provided between the cathode and the light emitting layer, and the electron transport region includes a compound represented by the following formula (3):
[Formula 3]

In Formula 3,
X1 is N or Q101, X2 is N or Q102, X3 is N or Q103,
At least one of X1 to X3 is N,
Q101 to Q103 and Q1 to Q3 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; hydroxyl group; Cyano group; nitro group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The organic light-emitting device of claim 22, wherein the electron transport region includes a compound represented by Formula 3, an organic alkali metal complex, or a mixture thereof. The organic light-emitting device according to claim 1, wherein one of A and B is a phenanthrene ring, a triphenylene ring, or a dibenzofuran ring.