CN113950754A

CN113950754A - Organic light emitting device

Info

Publication number: CN113950754A
Application number: CN202180003753.6A
Authority: CN
Inventors: 河宰承; 洪玩杓; 李豪中
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2020-01-20
Filing date: 2021-01-20
Publication date: 2022-01-18
Anticipated expiration: 2041-01-20
Also published as: WO2021150090A1; CN113950754B; KR20230078609A; KR20210093788A; KR102655910B1; KR102655907B1

Abstract

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

Description

Organic light emitting device

Technical Field

This application claims priority to korean patent application No. 10-2020-.

The present description relates to organic light emitting devices.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.

There is a continuing demand for the development of new materials for organic light emitting devices as described above.

Disclosure of Invention

Technical subject

The present specification provides an organic light emitting device.

Means for solving the problems

An embodiment of the present specification provides an organic light emitting device including: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; and a hole transport region including 2 or more organic layers provided between the light-emitting layer and the anode, wherein an organic layer in contact with the light-emitting layer among the organic layers contains a compound represented by the following chemical formula 1, and the light-emitting layer contains a compound represented by the following chemical formula 2.

[ chemical formula 1]

In the above-described chemical formula 1,

any one of R8 and R9 is a group represented by the following chemical formula a, a group other than the group represented by the following chemical formula a among the above-mentioned R8 and R9, R1 to R7, and R10 to R18, which are the same as or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or a group other than the group represented by the following chemical formula a among the above-mentioned R8 and R9, adjacent groups among R1 to R6, R7, and R10 to R18 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring,

[ chemical formula a ]

In the chemical formula a described above,

l1 to L3, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar1 and Ar2, which are the same or different from each other, are each independently deuterium, a halogen group, hydroxyl, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

l1 to l3 are each an integer of 1 to 3,

when L1 is 2 or more, the 2 or more L1 s may be the same or different from each other,

when L2 is 2 or more, the 2 or more L2 s may be the same or different from each other,

when L3 is 2 or more, the 2 or more L3 s may be the same or different from each other,

represents a site that binds to R8 or R9 of the above chemical formula 1,

[ chemical formula 2]

In the above-described chemical formula 2,

at least one of G1 to G10 is a group represented by the following chemical formula b, the remainder being the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[ chemical formula b ]

In the chemical formula b described above,

a and B are the same as or different from each other and are a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

l4 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

l4 is an integer from 1 to 3,

when L4 is 2 or more, the 2 or more L4 s may be the same or different from each other,

represents a site that binds to at least one of G1 to G10 of the above chemical formula 2,

the deuterium substitution rate of the above chemical formula 2 is 40% to 100%.

Effects of the invention

The organic light emitting device according to one embodiment of the present specification includes the compound of chemical formula 1 in an organic layer in contact with a light emitting layer and includes the compound of chemical formula 2 in the light emitting layer, and thus has a low driving voltage and an improved light efficiency, and the life characteristics of the device can be improved by utilizing the thermal stability of the compound.

Drawings

Fig. 1 to 4 illustrate an example of an organic light emitting device according to an embodiment of the present specification.

FIG. 5 is a diagram showing an MS chart of Compound A.

[ description of symbols ]

1: substrate

2: anode

3: hole transport region

4: luminescent layer

5: cathode electrode

3-1: hole transport layer

3-2: hole-regulating layer

6: hole injection layer

7: electron transport region

7-1: electronically regulated layer

7-2: electron transport layer

8: electron injection layer

Detailed Description

The present specification will be described in more detail below.

In the present specification, "deuterated" or "deuterated" means that a hydrogen of a position of a compound which can be substituted is replaced by deuterium.

In the present specification, "deuterated" refers to a compound or group in which all hydrogens in the molecule are replaced with deuterium, and has the same meaning as "100% deuterated".

In the present specification, "X% deuterated", "deuteration degree X%", or "deuterium substitution rate X%" means that X% of hydrogens at positions that can be substituted in the structure are substituted with deuterium. For example, when the structure is a dibenzofuran, "25% deuterated" the dibenzofuran, "25% deuterated of the dibenzofuran," or "25% deuterium substitution rate" of the dibenzofuran means that 2 of 8 hydrogens of the dibenzofuran at the substitutable position are substituted with deuterium.

In the present specification, "deuteration degree" or "deuterium substitution rate" can be determined by nuclear magnetic resonance spectroscopy (¹H NMR), TLC/MS (Thin Layer Chromatography/Mass Spectrometry), GC/MS (Gas Chromatography/Mass Spectrometry), or the like.

Specifically, the method is carried out by nuclear magnetic resonance spectroscopy (¹H NMR) analysis of "deuteration" or "deuterium substitution rate", DMF (dimethylformamide) may be added as an Internal standard (Internal standard) and passed¹The integration ratio on H NMR, the deuteration degree or deuterium substitution rate was calculated from the integrated amount of the total peak (peak).

When "deuteration degree" or "deuterium substitution rate" is analyzed by TLC/MS (thin layer chromatography/mass spectrometry), the substitution rate can be calculated based on the maximum value (median) of the distribution of molecular weights at the end of the reaction. For example, in analyzing the deuteration degree of the following compound a, the molecular weight of the following starting material was 506, and when it was pointed out that the maximum value (middle value) of the molecular weight of the following compound a in the MS chart of fig. 5 was 527, 21 of the hydrogens (26) of the positions that can be substituted of the following starting material were substituted with deuterium, and thus it could be calculated that about 81% of the hydrogens were deuterated.

In the present specification, D means deuterium.

In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.

In the present specification, the above-mentioned "layer" is used interchangeably with "film" mainly used in the art, and means a coating layer covering a target area. The size of the above "layer" is not limited, and the size of each "layer" may be the same or different. According to an embodiment, the size of the "layer" may be equal to the whole device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel (sub-pixel).

In the present specification, the meaning that a specific substance a is contained in a B layer is that i) the case where 1 or more substances a are contained in a B layer of one layer, and ii) the case where a B layer is composed of 1 or more layers and substances a are contained in 1 or more layers of a plurality of B layers are all included.

In the present specification, the meaning that the specific substance a is contained in the C layer or the D layer is that all cases where i) the substance a is contained in 1 or more of the 1 or more C layers, ii) the substance a is contained in 1 or more of the 1 or more D layers, or iii) the substance a is contained in the 1 or more C layers and the 1 or more D layers, respectively, are included.

In this specification, "or/and" means an inclusive "or/and" rather than an exclusive "or/and". For example, condition a or B satisfies any one of the following: a is true (or present) and B is false (or not present); a is false (or not present) and B is true (or present); both a and B are true (or present).

In the present specification, "a mixture of them" or "mixed" means that 2 or more substances are contained. The above-mentioned "mixture" or "mixing" may include a uniformly and/or non-uniformly mixed state, a dissolved state, a uniformly and/or non-uniformly dispersed state, and the like, but is not limited thereto.

In the present specification, unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. Methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, but are suitable for use with the methods and materials described below. All publications, patent applications, patents, and other references mentioned in this specification are herein incorporated in their entirety by reference into the specification, to the extent that a particular phrase (passage) is not specifically recited, in conflicting disclosure, priority is given to this specification, including definitions. Moreover, the materials, methods, and examples are illustrative only and not intended to be limiting.

In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.

In the context of the present specification,

indicating the site of attachment.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or more substituents selected from deuterium, a halogen group, hydroxyl, cyano, nitro, alkyl, cycloalkyl, alkoxy, alkenyl, haloalkyl, silyl, boryl, amino, aryl, and heteroaryl, or substituted with substituents formed by connecting 2 or more substituents among the above-exemplified substituents, or does not have any substituent.

In the present specification, the connection of 2 or more substituents means that hydrogen of any one substituent is connected to other substituents. For example, 2 substituents attached to a phenyl group and a naphthyl group can be

Such a substituent. Further, the connection of 3 substituents includes not only the connection of (substituent 1) - (substituent 2) - (substituent 3) continuously but also the connection of (substituent 2) and (substituent 3) in (substituent 1). For example, phenyl, naphthyl and isopropyl are linked to form

Such a substituent. The same definition as above applies to the case where 4 or more substituents are bonded.

In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

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

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2, 3-dimethylcyclohexyl group, a 3,4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, the above-mentioned haloalkyl group means hydrogen substituted with at least one halogen group in place of the alkyl group in the above definition of the alkyl group.

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

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

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. The number of carbon atoms is preferably 10 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a phenalene group, a perylenel group, a perylene group, a light-emitting element, and a light-emitting element,

And a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

In the case where the above-mentioned fluorenyl group is substituted, there are

And the like, but is not limited thereto.

In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.

In the present specification, the heteroaryl group contains 1 or more non-carbon atoms, that is, heteroatoms, and specifically, the above-mentioned heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,

Azolyl group,

Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthridinyl, phenanthrolinyl, isoquinoyl

Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiapyrrolyl, thiophenyl

Thienyl (phenoxathiine), thiophen

Examples of the oxazinyl group include, but are not limited to, an oxazinyl group, a phenothiazinyl group, a dihydroindenocarbazolyl group, a spirofluorenylxanthyl group, and a spirofluorenylthioxanthyl group.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like. Examples of the alkyl group can be applied to the alkyl group in the alkylsilyl group, examples of the aryl group can be applied to the aryl group in the arylsilyl group, and examples of the heteroaryl group can be applied to the heteroaryl group in the heteroarylsilyl group.

In the present specification, the boron group may be-BR₁₀₀R₁₀₁R is as defined above₁₀₀And R₁₀₁The same or different, may each be independently selected from the group consisting of hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group of carbon number 3 to 30, a substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the amine group may be selected from-NH₂The number of carbon atoms of the alkylamino group, the N-alkylarylamino group, the arylamine group, the N-arylheteroarylamino group, the N-alkylheteroarylamino group and the heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, ditolylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrylamino, N-biphenylphenanthrylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, N-biphenylfluorenylamino, and the like。

In the present specification, an N-alkylarylamino group means an amino group substituted with an alkyl group and an aryl group on the N of the amino group. The alkyl group and the aryl group in the above-mentioned N-alkylarylamino group are the same as those exemplified above.

In this specification, an N-arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group on the N of the amine group. The aryl and heteroaryl groups in the above N-arylheteroarylamino group are exemplified by the same aryl and heteroaryl groups as described above.

In the present specification, an N-alkylheteroarylamine group means an amine group substituted with an alkyl group and a heteroaryl group on the N of the amine group. The alkyl group and the heteroaryl group in the above-mentioned N-alkylheteroarylamino group are exemplified by the same alkyl groups and heteroaryl groups as those described above.

In the present specification, as examples of the alkylamino group, there are a substituted or unsubstituted monoalkylamino group, or a substituted or unsubstituted dialkylamino group. The alkyl group in the above-mentioned alkylamino group may be a linear or branched alkyl group. The alkylamino group containing 2 or more of the above alkyl groups may contain a linear alkyl group, a branched alkyl group, or may contain both a linear alkyl group and a branched alkyl group. For example, the alkyl group in the alkylamino group can be selected from the above-mentioned examples of alkyl groups.

In the present specification, as an example of the arylamine group, there is 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 2 or more of the above-mentioned aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, or a substituted or unsubstituted diheteroarylamino group. Heteroarylamine groups comprising more than 2 of the above-described heteroaryls may comprise a monocyclic heteroaryl, a polycyclic heteroaryl, or may comprise both a monocyclic heteroaryl and a polycyclic heteroaryl. For example, the heteroaryl group in the heteroarylamino group can be selected from the examples of the heteroaryl group described above.

In the present specification, the phrase "adjacent 2 groups combine with each other to form a ring" in a substituent means that adjacent groups combine with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the cycloalkyl groups and the aryl groups described above, except that the hydrocarbon ring has a valence of not 1.

In the present specification, the heterocyclic ring contains 1 or more heteroatoms other than carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocyclic ring may be selected from the heteroaryl groups, except that it has a valence of 1.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more heteroatoms. Examples of the aliphatic heterocyclic ring include ethylene oxide (oxirane), tetrahydrofuran, and 1, 4-bis

Examples of the alkyl group include, but are not limited to, alkyl (1,4-dioxane), pyrrolidine, piperidine, morpholine (morpholinone), oxepane, azocane, and thiacyclooctane.

In the present specification, arylene means a group having two binding sites on an aryl group, i.e., a 2-valent group. The above description of aryl groups applies, except that they are each a 2-valent group.

In this specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. The above description of heteroaryl groups applies in addition to each being a 2-valent group.

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

The organic light emitting device according to the above embodiment is characterized in that the compound of chemical formula 1 is contained between the anode and the light emitting layer, i.e., in the hole transport region, and the compound of chemical formula 2 is contained in the light emitting layer. By including the compound of formula 1 in the hole transport region of the organic light emitting device, thereby accelerating the injection and transport of holes, maximizing the transport of carriers into the inside of the light emitting layer, and thus the efficiency of the light emitting layer can be improved, and by including the compound of formula 2 in the light emitting layer, thereby a device having an excellent lifetime can be obtained.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 40% to 100%, preferably 40% to 99%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 45% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 50% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 65% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 70% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 80% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 90% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 2 is 100%.

The deuterium substitution rate can be calculated by the method described above. According to an additional example, the anthracene of chemical formula 2 above is directly substituted with at least one deuterium. The light-emitting layer of the organic light-emitting device is a light-emitting region and is a region where loss of molecules due to energy is large. Since carbon-deuterium bonds are stronger than carbon-hydrogen bonds, deuterium has a higher mass value than hydrogen, and Zero energy (Zero point energy) with carbon is reduced, so that the bond energy with the molecule is high, the carbon-hydrogen bonds contained in the molecule of the compound of the above chemical formula 2 are replaced with carbon-deuterium bonds to increase the bond energy of the molecule, so that a device having an excellent lifetime can be obtained.

The organic light emitting device including the compound of chemical formula 2 having the deuterium substitution rate according to an embodiment of the present specification has the effect of improving the lifetime.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 1 is 0% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 1 is 0.01% to 100%.

According to an embodiment of the present disclosure, the deuterium substitution rate of chemical formula 1 is 1% to 100%.

According to an embodiment of the present specification, at least one of hydrogens at a position of the chemical formula 1 which may be substituted is substituted with deuterium.

According to an embodiment of the present disclosure, any one of R8 and R9 is a group represented by chemical formula a, and the group other than the group represented by chemical formula a among R8 and R9, R1 to R7 and R10 to R18, which are the same or different from each other, are each independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, or the group other than the group represented by chemical formula a among R8 and R9, and adjacent groups among R1 to R6, R7 and R10 to R18 are bonded to each other to form a polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an embodiment of the present disclosure, the group other than the group represented by the following chemical formula a among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an embodiment of the present disclosure, the groups other than the group represented by the following chemical formula a among R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an embodiment of the present disclosure, the groups other than the group represented by the following chemical formula a, among the above-described R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a substituted or unsubstituted benzene ring.

According to an embodiment of the present disclosure, the groups other than the group represented by the following chemical formula a, among the above-described R8 and R9, and adjacent groups among R1 to R6, R7, and R10 to R18 are bonded to each other to form a benzene ring.

According to an embodiment of the present disclosure, R1 and R18 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

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

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

According to an embodiment of the present disclosure, R1 and R18 are bonded to each other to form an aromatic hydrocarbon ring.

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

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

According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

In the above chemical formulas 1-1 to 1-4,

r2 to R17, R101 and R118, which are identical to or different from one another, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,

l1 to L3, L1 to L3, Ar1 and Ar2 are as defined above for formula a.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, of the above-mentioned R8 and R9, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to an embodiment of the present disclosure, the group other than the group represented by the following chemical formula a among the above-mentioned R8 and R9, R1 to R7, and R10 to R18, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present disclosure, among the above-mentioned R8 and R9, a group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present disclosure, among the above-mentioned R8 and R9, a group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, of the above-mentioned R8 and R9, are each independently hydrogen, deuterium, an alkyl group, or an aryl group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, of R8 and R9, are each independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, of R8 and R9, are each independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, of R8 and R9, are each independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 10 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms which is substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, and R10 to R18, which are the same or different from each other, of the above-mentioned R8 and R9, are each independently hydrogen, deuterium, tert-butyl, or phenyl substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R7, R11, and R13 to R18, among the above-described R8 and R9, are hydrogen.

According to an embodiment of the present disclosure, R12 is hydrogen, tert-butyl or phenyl.

According to an embodiment of the present specification, the group other than the group represented by the following chemical formula a, R1 to R6, and R12 to R18, among the above-described R8 and R9, are hydrogen.

According to an embodiment of the present disclosure, R7 is phenyl substituted with deuterium.

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

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

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

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

According to one embodiment of the present disclosure, L1 to L3 are the same or different and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

According to an embodiment of the present disclosure, L1 to L3 are the same or different and each independently a direct bond, a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an embodiment of the present disclosure, L1 to L3 are the same or different and each independently a direct bond, a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an embodiment of the present disclosure, L1 to L3 are the same or different and are each independently a direct bond; arylene substituted or unsubstituted with 1 or more selected from deuterium, alkyl, and aryl; or a heteroarylene group substituted or unsubstituted with deuterium or alkyl.

According to an embodiment of the present disclosure, L1 to L3 are the same or different and are each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group of 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium or a linear or branched alkyl group of 1 to 30 carbon atoms.

According to an embodiment of the present disclosure, L1 to L3 are the same or different and are each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more selected from deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group of 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium or a linear or branched alkyl group of 1 to 20 carbon atoms.

According to an embodiment of the present disclosure, L1 to L3 are the same or different and are each independently a direct bond; phenylene substituted or unsubstituted with deuterium; biphenylene substituted or unsubstituted with deuterium; terphenylene substituted or unsubstituted with deuterium; a 2-valent fluorenyl group substituted with 1 or more selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a 2-valent benzofuranyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, L1 to L3 are the same or different and are each independently a direct bond; phenylene substituted or unsubstituted with deuterium; biphenylene substituted or unsubstituted with deuterium; terphenylene substituted or unsubstituted with deuterium; a 2-valent fluorenyl group substituted with 1 or more selected from deuterium, methyl, and phenyl; or a 2-valent benzofuranyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the L1 to L3 are the same as or different from each other, and each independently represents a directly bonded group, a phenylene group substituted with deuterium or unsubstituted, a biphenylene group, a terphenylene group, a 2-valent fluorenyl group substituted with 1 or more selected from a methyl group and a phenyl group, or a 2-valent benzofuranyl group.

According to one embodiment of the present disclosure, L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

According to one embodiment of the present disclosure, L1 is a direct bond, a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, L1 is a directly bonded, substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, or substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to one embodiment of the present disclosure, L1 is a directly bonded, substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms, or substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.

According to one embodiment of the present disclosure, L1 is a direct bond, an arylene group substituted or unsubstituted with deuterium, or a heteroarylene group.

According to one embodiment of the present disclosure, L1 is a directly bonded, deuterium substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms or monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, L1 is a directly bonded, deuterium substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms or monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to one embodiment of the present disclosure, L1 is a directly bonded, deuterium substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms or monocyclic or polycyclic heteroarylene group having 2 to 15 carbon atoms.

According to one embodiment of the present disclosure, L1 is a direct bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group substituted or unsubstituted with deuterium, or a benzofuranyl group having a valence of 2.

According to one embodiment of the present disclosure, L1 is a phenylene group, a biphenylene group, or a 2-valent benzofuranyl group which is directly bonded, substituted with deuterium, or unsubstituted.

According to an embodiment of the present disclosure, L2 and L3 are the same or different from each other and each independently is a direct bond, or a substituted or unsubstituted arylene group.

According to an embodiment of the present disclosure, L2 and L3 are the same or different and each independently a direct bond or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an embodiment of the present disclosure, L2 and L3 are the same or different and each independently a direct bond or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an embodiment of the present disclosure, L2 and L3 are the same or different from each other and are each independently a direct bond; or an arylene group substituted or unsubstituted with 1 or more selected from deuterium, an alkyl group and an aryl group.

According to an embodiment of the present disclosure, L2 and L3 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more members selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present disclosure, L2 and L3 are the same or different from each other and are each independently a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more members selected from deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present disclosure, L2 and L3 are the same or different from each other and are each independently a direct bond; phenylene substituted or unsubstituted with deuterium; biphenylene substituted or unsubstituted with deuterium; terphenylene substituted or unsubstituted with deuterium; or a 2-valent fluorenyl group substituted with 1 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 embodiment of the present disclosure, L2 and L3 are the same or different from each other and are each independently a direct bond; phenylene substituted or unsubstituted with deuterium; biphenylene substituted or unsubstituted with deuterium; terphenylene substituted or unsubstituted with deuterium; or a 2-valent fluorenyl group substituted by 1 or more selected from deuterium, methyl, and phenyl.

According to an embodiment of the present specification, the L2 and the L3 are the same as or different from each other, and each independently represents a direct bond, a phenylene group substituted with deuterium or unsubstituted, a biphenylene group, a terphenylene group, or a 2-valent fluorenyl group substituted with 1 or more selected from a methyl group and a phenyl group.

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

According to an embodiment of the present disclosure, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with 1 or more members selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group of 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more members selected from deuterium, a linear or branched alkyl group of 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms.

According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with 1 or more groups selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium, and a linear or branched alkylsilyl group having 1 to 30 carbon atoms; biphenyl substituted or unsubstituted with 1 or more selected from deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms; a terphenyl group; a tetra-biphenyl group; naphthyl substituted or unsubstituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; a triphenylene group; a fluorenyl group substituted with 1 or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms substituted with deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a carbazolyl group; a dibenzofuranyl group; benzofuranyl which is unsubstituted or substituted by a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or dibenzothienyl.

According to an embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with 1 or more selected from deuterium, tert-butyl, trimethylsilyl, methyl, and phenyl; biphenyl substituted or unsubstituted with 1 or more selected from deuterium and tert-butyl; a terphenyl group; a tetra-biphenyl group; naphthyl substituted or unsubstituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; a triphenylene group; fluorenyl substituted with 1 or more selected from deuterium, trideuteromethyl, methyl and phenyl; a carbazolyl group; a dibenzofuranyl group; benzofuranyl substituted or unsubstituted with phenyl; or dibenzothienyl.

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

According to an embodiment of the present disclosure, at least one of G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other, and each independently represents hydrogen, deuterium, or a substituted or unsubstituted aryl group.

According to an embodiment of the present disclosure, at least one of G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other, and each independently represents hydrogen, deuterium, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present disclosure, at least one of G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other and each independently represent hydrogen; deuterium; or a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more selected from deuterium and a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, at least one of G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group having 1 or more carbon atoms selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium; naphthyl substituted or unsubstituted by 1 or more selected from deuterium and monocyclic or polycyclic aryl groups of 6 to 30 carbon atoms substituted or unsubstituted by deuterium; biphenyl substituted or unsubstituted with 1 or more selected from deuterium and monocyclic or polycyclic aryl groups of 6 to 30 carbon atoms substituted or unsubstituted with deuterium; terphenyl substituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; a triphenylene group substituted or unsubstituted with deuterium; or a pyrenyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, at least one of G1 to G10 is a group represented by the following chemical formula b, and the others are the same or different from each other and each independently represent hydrogen; deuterium; phenyl substituted or unsubstituted with 1 or more selected from deuterium, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, and naphthyl substituted or unsubstituted with deuterium; naphthyl substituted or unsubstituted with 1 or more selected from deuterium, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, and naphthyl substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with 1 or more selected from deuterium and a phenyl group substituted or unsubstituted with deuterium; terphenyl substituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; a triphenylene group substituted or unsubstituted with deuterium; or a pyrenyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, G1 is a group represented by formula b.

According to an embodiment of the present disclosure, G3 is a group represented by formula b.

According to an embodiment of the present disclosure, G1 and G6 are the same or different from each other, and each is a group represented by the chemical formula b.

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

According to an embodiment of the present disclosure, L4 is a direct bond or a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, L4 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is directly bonded or substituted or unsubstituted.

According to one embodiment of the present disclosure, L4 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms which is directly bonded or substituted or unsubstituted.

According to one embodiment of the present disclosure, L4 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is directly bonded or substituted with deuterium or unsubstituted.

According to one embodiment of the present disclosure, L4 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms which is directly bonded or substituted with deuterium or unsubstituted.

According to an embodiment of the present disclosure, L4 is a direct bond, a phenylene group substituted or unsubstituted with deuterium, or a naphthylene group substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, a and B are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

According to an embodiment of the present disclosure, a and B are the same or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, a and B are the same as or different from each other, and each independently represents a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with 1 or more members selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with deuterium; or a monocyclic or polycyclic heterocycle of 2 to 30 carbon atoms substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, a and B are the same as or different from each other, and each independently represents 1 or more substituted or unsubstituted benzene rings selected from deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium; a naphthalene ring substituted or unsubstituted with deuterium; phenanthrene rings substituted or unsubstituted with deuterium; a triphenylene ring substituted or unsubstituted with deuterium; or a dibenzofuran ring substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, a and B are the same as or different from each other, and each independently represents 1 or more substituted or unsubstituted benzene rings selected from deuterium, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with deuterium; a naphthalene ring substituted or unsubstituted with deuterium; phenanthrene rings substituted or unsubstituted with deuterium; a triphenylene ring substituted or unsubstituted with deuterium; or a dibenzofuran ring substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, the chemical formula 1 is any one selected from the following compounds.

According to an embodiment of the present disclosure, the chemical formula 2 is any one selected from the following compounds.

According to one embodiment of the present disclosure, the compounds of

chemical formulas

1 and 2 can be produced using starting materials and reaction conditions known in the art. The kind and number of the substituents can be determined by appropriately selecting known starting materials by those skilled in the art. Further, the compounds of the

above chemical formulas

1 and 2 can be obtained from commercially available compounds.

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

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

In the above-mentioned structural formula, the polymer,

t1 to T3, which are identical to or different from each other, are each independently deuterium, a halogen group, hydroxyl, cyano, nitro, alkyl, cycloalkyl, alkoxy, alkenyl, haloalkyl, silyl, boryl, amine, aryl or heteroaryl, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,

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

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

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

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

According to one embodiment of the present disclosure, the organic layer includes a hole transport layer and a hole control layer, and the hole transport layer includes the compound represented by chemical formula 1.

According to one embodiment of the present disclosure, the organic layer includes a hole transport layer and a hole control layer, and the hole control layer includes a compound represented by the chemical formula 1.

The hole regulating layer according to an embodiment of the present specification includes a compound represented by the above chemical formula 1, and the deuterium substitution rate of the above chemical formula 1 is 1% to 100%.

According to one embodiment of the present disclosure, a hole transport region is provided between the anode and the light-emitting layer, the hole transport region includes the hole transport layer and a hole control layer, and the hole transport layer is provided in contact with the hole control layer.

According to one embodiment of the present specification, the hole-adjusting layer is provided in contact with the light-emitting layer.

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

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

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

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

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

Fig. 4 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 6, a hole transport region 3 including a hole transport layer 3-1 and a hole adjusting layer 3-2, a light emitting layer 4, an electron transport region 7 including an electron adjusting layer 7-1 and an electron transport layer 7-2, an electron injection layer 8, and a cathode 5 are sequentially stacked on a substrate 1. Fig. 4 is an exemplary structure according to an embodiment of the present disclosure, and may further include another organic layer.

According to one embodiment of the present disclosure, the thickness of the hole transport layer is 50nm to 200 nm.

According to one embodiment of the present disclosure, the thickness of the hole-control layer is 10nm to 150 nm.

The hole transport region is formed of plural or singular layers including a hole transport layer and a hole adjusting layer, and the thickness of the hole transport region may be determined based on an optimum point within the thickness in order to optimize optical characteristics of the organic light emitting device.

According to an embodiment of the present disclosure, the triplet energy of the chemical formula 1 is 2.4eV to 2.8 eV.

In the hole transport region according to one embodiment of the present specification, the layer in contact with the light-emitting layer, that is, the layer including the layer of the above chemical formula 1, has the above triplet energy range, generally exhibits relatively high singlet energy, and therefore generally has a low maximum occupied orbital energy. Therefore, carriers and excitons in the light-emitting layer are less likely to migrate or transition, and thus the efficiency of the fabricated organic light-emitting device can be improved, and stability can be brought about.

In the present specification, "energy level" refers to the magnitude of energy. Therefore, the energy level is interpreted as an absolute value representing the energy value. For example, a low or deep energy level means an increase in absolute value in a negative direction from the vacuum level.

In the present specification, HOMO (highest occupied molecular orbital) refers to a molecular orbital function (highest occupied molecular orbital) of a region with the highest energy in which an electron is located in a region that can participate in binding, LUMO (lowest unoccupied molecular orbital) refers to a molecular orbital function (lowest unoccupied molecular orbital) of a region with the lowest energy in which an electron is located in an anti-binding region, and HOMO level refers to a distance from a vacuum level to HOMO. Further, the LUMO level refers to the distance from the vacuum level to the LUMO. In order to grasp the electron distribution in the molecule and grasp the optical properties, a specific structure is required. The electronic structure has different structures in neutral, anionic, and cationic states depending on the charge state of the molecule. For driving the device, energy levels of a neutral state, a cation state, and an anion state are important, but typically, HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) of the neutral state are considered to be important physical properties. To determine the molecular structure of a chemical species, the input structure is optimized using a density functional theory (density functional theory). For the DFT calculation, the BPW91 algorithm (beck exchange function and per correlation function) and the DNP (double numerical basis of polarization function) basis set (basis set) are used. The BPW91 algorithm is disclosed in the paper "a.d. becke, phys.rev.a,38,3098 (1988)", and "j.p. perew and y.wang, phys.rev.b,45,13244 (1992)", the DNP basis set is disclosed in the paper "b.delley, j.chem. phys.,92,508 (1990)".

For the calculation by the density functional method, package (package) of "DMol 3" of Biovia corporation can be used. When the optimum molecular structure is determined by the method given above, the energy level that can be occupied by electrons can be obtained as a result.

In the present specification, triplet energy refers to an electron state in which the number of spin quanta in a molecule is 1. In order to obtain the physical properties of the excited state of the optimum molecular structure determined by the above method, the energy levels of the singlet state and the triplet state are calculated by a time dependent density functional theory (TD-DFT) method. The density functional calculations may be performed using the commercial calculation program "Gaussian 09" package developed by Gaussian (Gaussian) corporation. For time-dependent density functional calculations, the B3PW91 algorithm (Becke exchange function and persew correlation function) and the 6-31G base set were used. The basic set of 6-31G is disclosed in the paper "j.a. pople et al, j.chem.phys.56,2257 (1972)". For the optimal molecular structure determined using the density functional method, the energy possessed by electrons when they are arranged in a singlet state (single) and a triplet state (triplet) was calculated using the time-dependent density functional method (TD-DFT).

According to one embodiment of the present disclosure, the light-emitting layer includes a host and a dopant.

According to one embodiment of the present disclosure, the organic electroluminescent device includes the host and a dopant, and the host includes a compound represented by the chemical formula 2.

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

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

According to one embodiment of the present disclosure, the light emitting layer includes 2 or more kinds of mixed hosts, and 1 or more kinds of the 2 or more kinds of mixed hosts include the compound represented by chemical formula 2.

According to one embodiment of the present disclosure, the light emitting layer includes 2 or more kinds of mixed hosts, at least 1 of the 2 or more kinds of mixed hosts includes a compound represented by the chemical formula 2, and the rest includes an anthracene-based compound not including deuterium as a substituent.

According to one embodiment of the present disclosure, the light emitting layer includes 2 or more kinds of mixed hosts, at least 1 of the 2 or more kinds of mixed hosts includes a compound represented by the chemical formula 2, and the rest includes an anthracene-based compound including deuterium as a substituent and different from the chemical formula 2.

According to one embodiment of the present disclosure, the light emitting layer includes 2 or more kinds of mixed hosts, at least 1 of the 2 or more kinds of mixed hosts includes a compound represented by the chemical formula 2, and the rest includes 1 or more kinds selected from an anthracene-based compound not including deuterium as a substituent and an anthracene-based compound including deuterium as a substituent and different from the chemical formula 2.

At least 1 of the 2 or more kinds of mixed hosts includes the compound represented by the chemical formula 2, and the anthracene-based host used in the present technical field may be used without limitation as long as the rest is different from the chemical formula 2, and is not limited thereto.

The organic light emitting device using 2 or more kinds of mixed hosts according to an embodiment of the present specification mixes advantages of the respective hosts to improve the performance of the device, and for example, when 2 kinds of hosts are mixed, 1 kind of hosts having high efficiency and low voltage effects and 1 kind of hosts having long life effects are mixed, so that an organic light emitting device having high efficiency, low voltage, and long life effects can be manufactured.

According to one embodiment of the present disclosure, the organic light emitting device has a maximum emission wavelength (λ) of an emission spectrum_{Maximum of}) From 400nm to 470 nm.

According to one embodiment of the present disclosure, the light-emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes 1 or more selected from a pyrene-based compound and a non-pyrene-based compound.

The pyrene-based compound and the non-pyrene-based compound are not limited to the above compounds, and any compounds used in the art may be used.

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

According to one embodiment of the present disclosure, the light emitting layer includes a host including a compound represented by the chemical formula 2 and a dopant including 1 or more selected from pyrene-based compounds and non-pyrene-based compounds.

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

According to one embodiment of the present disclosure, the organic light emitting device includes an electron transport region disposed between the cathode and the light emitting layer.

According to one embodiment of the present disclosure, the organic light emitting device includes an electron transport region disposed between the cathode and the light emitting layer, the electron transport region including a compound represented by the following chemical formula 3.

[ chemical formula 3]

In the above-mentioned chemical formula 3,

x1 is N or Q101, X2 is N or Q102, X3 is N or Q103,

at least one of the above X1 to X3 is N,

q101 to Q103 and Q1 to Q3, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an embodiment of the present specification, the electron transport region is not limited to any one as long as it is a monocyclic six-membered heterocyclic compound, that is, a triazine derivative, a pyrimidine derivative, and a pyridine derivative.

According to one embodiment of the present disclosure, the electron transport region includes a compound represented by the chemical formula 3, an organic alkali metal complex, and a mixture thereof. At this time, as the organic alkali metal complex, lithium quinolate and aluminum quinolate may be used, but not limited thereto, and the content of the organic alkali metal complex is 10 to 90 wt%, preferably 30 to 70 wt%, based on the material of the organic layer.

According to an embodiment of the present disclosure, the electron transport region includes an electron transport layer and an electron adjustment layer.

According to an embodiment of the present disclosure, the organic light emitting device may include only the hole transport region and the light emitting layer as organic layers, but may further include additional organic layers. For example, additional hole injection layers, hole transport layers, electron blocking layers, light emitting layers, hole blocking layers, electron transport layers, electron injection layers, and the like may also be included.

According to an embodiment of the present disclosure, the organic light emitting device may further include an additional organic layer. The additional organic layer may have 1 or more layers of a light emitting layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron regulation layer, an electron blocking layer, a hole blocking layer, and a hole regulation layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.

In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.

In the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

In the organic light emitting device of the present specification, a layer adjacent to the light emitting layer among the organic layers includes the compound represented by the above chemical formula 1, and the light emitting layer includes the compound represented by the above chemical formula 2, and in addition, it can be manufactured using materials and methods known in the art.

For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. This can be produced as follows: the organic el display device is manufactured by forming an anode by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (e-beam evaporation) method, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.

In addition to these methods, an organic light-emitting device may be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂Multilayer structure materials such as/Al, Mg/Ag, etc., but not limited thereto.

A capping layer for protecting the electrode may be further formed on the cathode, and the capping material may be appropriately used as a material used in the art.

The hole injection layer is a layer for injecting holes from the electrode as a hole injection substance, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting species is between the work function of the anode species and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The electron blocking layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, and thus can improve the lifetime and efficiency of the device, and may be formed using a known material at an appropriate portion between the light emitting layer and the electron injection layer.

The light-emitting substance of the light-emitting layer is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and when the organic light-emitting device of the present specification includes an additional light-emitting layer in addition to the light-emitting layer including the compound represented by chemical formula 2, it is preferable that the substance has high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is 8-hydroxy-quinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is

Azole, benzothiazole and benzimidazole seriesA compound; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.

An electron adjusting layer may be further provided between the light emitting layer and the electron transporting layer. The electron adjusting layer substance may suitably use materials used in this technical field.

The electron transport material in the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material is a material that can satisfactorily receive electrons from the cathode and transfer the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

The hole blocking layer is a layer that prevents holes from reaching the cathode and can be formed under the same conditions as those of the hole injection layer. Specifically, there are

An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

The structure according to one embodiment of the present specification can function on a principle similar to that applied to an organic light-emitting device in an organic electronic device typified by an organic solar cell, an organic photoreceptor, an organic transistor, or the like.

Modes for carrying out the invention

The fabrication of the above-described organic light emitting device is specifically described in the following examples. However, the following examples are provided to illustrate the present specification, and the scope of the present specification is not limited thereto.

Production example (Synthesis of BH)

The reaction (1 equivalent), triflic acid (triflic acid) (catalyst (cat.)) was added to C₆D₆(10 to 50 times the mass of the reaction product) at 70 ℃ for 10 to 100 minutes. After the reaction is finished, D is added₂O (excess), stirring for 30 minutes, and then dropwise adding trimethylamine (excess). The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was washed with MgSO₄After drying, recrystallization was performed by heating with toluene, and the products in tables 1 and 2 below were obtained.

[ Table 1]

The degree of deuterium substitution differs depending on the reaction time of each product, and the substitution rate is determined by the maximum M/z (M +) value.

The above-mentioned reactants were synthesized by referring to the existing documents of this company such as KR1964435, KR1899728, KR1975945, KR2018-0098122, KR2018-0102937 and KR 2018-0103352. For deuterium substitution of the above product, reference is made to KR 1538534.

[ Table 2]

The above reactants were synthesized according to the prior literatures of this company such as KR1994238B1, KR1670193B1, KR1754445B1, and KR1368164B 1. For deuterium substitution of the above product, reference is made to the prior art document KR1538534B 1.

In addition, compounds 1-21 to 1-22 and BH3 (deuterium substitution rate 0%), BH4 (deuterium substitution rate 25%) and BH5 (deuterium substitution rate 35%) having deuterium substitution rates of 40% and 65%, respectively, were synthesized with reference to the above-mentioned prior art documents, and further comparative experiments of compounds having deuterium substitution rates different from each other were conducted.

The products of tables 1 and 2, compounds 1 to 21 and 1 to 22 were synthesized by referring to prior documents such as JP4070676B2, KR1477844B1, US6465115B2, JP3148176B2, JP4025136B2, JP4188082B2, JP5015459B2, KR1979037B1, KR1550351B1, KR1503766B1, KR0826364B1, KR0749631B1, KR1115255B1 and the like. Further, deuterium (-D) incorporated in the resultant synthesized in tables 1 and 2 above means that incorporation can be made at the indicated position, and does not mean that incorporation is necessary at the indicated position.

In addition, the following compounds 3-1 to 3-18, which are compounds represented by the above chemical formula 1 contained in the following hole transport region, were synthesized with reference to JP2015-530364A, US5840217A, WO2013-120577A, KR2016-0035610 a.

< comparative examples 1-1> production of organic light-emitting device

As anode, will be 70/1000

The ITO/Ag/ITO-evaporated substrate was cut into a size of 50 mm. times.50 mm. times.0.5 mm, and placed in distilled water in which a dispersant was dissolved, and washed by ultrasonic waves. The detergent used was a product of Fisher Co, and the distilled water was filtered 2 times using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.

On the anode thus prepared, HI-1 was added

Is formed by thermal vacuum evaporation, and on the hole injection layer, HT1 as a hole transport substance is formed in a thickness of

Vacuum evaporation is performed to form a hole transport layer. Next, EB1 is utilized

To form a hole-adjusting layer, followed by adding BH1 and a dopant BD1(2 wt.%) to the layer

The thickness of (2) is vacuum-evaporated to form a light-emitting layer. Then, HB1 was evaporated

An electron adjusting layer was formed, and a thickness was formed by mixing the compound ET1 and Liq at a mass ratio of 5:5

The electron transport layer of (1). In turn will

Magnesium and lithium fluoride (LiF) as electron injection layers in thickness<EIL>Formed into a film and then used as a cathode, to

Magnesium and silver (1:4) are formed, and then CP1 is evaporated

Thereby completing the device. In the above process, the evaporation speed of the organic material is maintained

In seconds.

< comparative examples 1-2 to 1-15 and examples 1-1 to 1-43>

Organic light-emitting devices were produced in the same manner as in comparative example 1-1 except that in comparative example 1-1, compounds of table 3 below were used as hosts of the light-emitting layer instead of BH1 and EB1 was used as a hole-regulating layer instead of EB1, respectively, and the structures of the organic light-emitting devices produced in comparative examples 1-1 to 1-15 and examples 1-1 to 1-43 are shown in table 3, and table 4 below is a 20mA/cm for comparative examples 1-1 to 1-15 and examples 1-1 to 1-43²The current density of (2) was measured, and the results of the measurement of the driving voltage, the luminous efficiency, and the time (LT95) at which the luminance was 95% of the initial luminance were obtained.

[ Table 3]

[ Table 4]

In the above tables 3 and 4, the organic light emitting device according to an embodiment of the present specification shows excellent hole injection and transport capability to the light emitting layer by using the compound of chemical formula 1 suitable for the hole transport region of the blue organic electroluminescent device and the compound of chemical formula 2 used as a host of the light emitting layer. In addition, the organic light emitting device according to the present specification shows superior characteristics in efficiency, driving voltage, stability, as compared to the organic light emitting device including chemical formula 1 or chemical formula 2, respectively, through the balance of holes and electrons according to the organic light emitting device of chemical structure.

In particular, the results regarding the device characteristics according to the deuterium substitution rate of the above chemical formula 2 can also be observed from the results of the above tables 3 to 4. Comparative examples 1-11 to 1-13 using compounds in which the deuterium substitution rates of the compounds 1 to 6 were unsubstituted (0%), 20% and 35%, respectively, exhibited significantly lower lifetimes as compared to examples 1-6, 1-42 and 1-43 using compounds in which the deuterium substitution rate was 40% or more, and were found to have no lifetime-increasing effect due to deuterium substitution. On the contrary, in examples 1 to 6, 1 to 42 and 1 to 43 in which the deuterium substitution rate of chemical formula 2 is 40% or more, the lifetime of the device is significantly improved as compared with comparative examples 1 to 11 to 1 to 13, and it is understood that the deuterium substitution rate of chemical formula 2 must be 40% or more, and the lifetime of the device is significantly improved.

Further, when the above examples 1 to 42 and 1 to 43 are compared with the comparative examples 1 to 14 and 1 to 15, it is understood that the life span of the examples 1 to 42 and 1 to 43 in which the substitution rate of deuterium of the above chemical formula 2 is 40% or more is greatly increased, and the efficiency and the driving voltage are also excellent.

< comparative example 2-1> production of organic light-emitting device

As anode, will be 70/1000

The ITO/Ag/ITO-evaporated substrate was cut into a size of 50 mm. times.50 mm. times.0.5 mm, and placed in distilled water in which a dispersant was dissolved, and washed by ultrasonic waves. The detergent used was a product of Hill corporation, and distilled water was filtered 2 times through a filter manufactured by Millipore corporation. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.

On the anode thus prepared, HI-1 was added

To form a hole-adjusting layer, followed by adding BH1 and a dopant BD2(2 wt.%) to the layer

To form electronsAdjusting the layer, mixing the compound ET1 and Liq at a mass ratio of 5:5 to form a thickness

The electron transport layer of (1). In turn will

Magnesium and silver (1:4) are formed, followed by CP1 evaporation

In seconds.

< comparative examples 2-2 to 2-10 and examples 2-1 to 2-41>

Organic light-emitting devices were produced in the same manner as in comparative example 2-1 except that in comparative example 2-1, compounds of table 5 below were used as hosts of the light-emitting layer instead of BH1 and EB1 was used as a hole-regulating layer instead of EB1, respectively, and the structures of the organic light-emitting devices produced in comparative examples 2-1 to 2-10 and examples 2-1 to 2-41 are shown in table 5, and table 6 below is a graph showing the structures of the organic light-emitting devices produced at 20mA/cm for comparative examples 2-1 to 2-10 and examples 2-1 to 2-41²The current density of (2) was measured, and the results of the measurement of the driving voltage, the luminous efficiency, and the time (LT95) at which the luminance was 95% of the initial luminance were obtained.

[ Table 5]

[ Table 6]

In the above tables 3 to 6, the organic light emitting device according to an embodiment of the present specification shows excellent hole injection and transport ability into the light emitting layer by using the compound of chemical formula 1 suitable for the hole transport region of the blue organic electroluminescent device and the compound of chemical formula 2 used as the host of the light emitting layer. In addition, the organic light emitting device according to the present specification shows superior characteristics in efficiency, driving voltage, stability, as compared to the organic light emitting device including chemical formula 1 or chemical formula 2, respectively, through the balance of holes and electrons according to the organic light emitting device of chemical structure.

Examples 1-1 to 1-38, 1-42, 1-43, and 2-1 to 2-38 described above were each produced by using the compound of the above chemical formula 1 alone as a hole transport layer and the compound of the above chemical formula 2 alone as a host of a light emitting layer. The structure of the device shows that BD1 or BD2 can be applied to various hole-regulating layers corresponding to the above chemical formula 1 and various blue host and blue fluorescent dopants corresponding to the above chemical formula 2. Further, examples 1-39 to 1-41 and 2-39 to 2-41 show that 2 hosts corresponding to chemical formula 2 are used as a mixed host, so that the performance of the device can be improved.

The above comparative examples 1-1 to 1-6, 1-11 to 1-13, and 2-1 to 2-6 are results of devices fabricated with a compound that is not a combination of the

compounds

1 and 2 according to an embodiment of the present specification, and anthracene of the aryl system example was used as a host of the light-emitting layer. This case all showed high voltage, low efficiency, low lifetime, showing low performance of the device.

The above comparative examples 1-7, 1-8, 1-14, 1-15, 2-7 and 2-8 are results of applying only the hole regulating layer corresponding to the above chemical formula 1, and a small driving voltage lowering tendency was observed as compared with the comparative examples 1-1 to 1-6, 1-11 to 1-13 and 2-1 to 2-6, but it was seen that the improvement of the device performance as a whole was not achieved. Further, the above-mentioned comparative examples 1-9, 1-10, 2-9 and 2-10 are results of applying only the blue host corresponding to the above chemical formula 2, and an improvement in the overall life can be observed as compared with comparative examples 1-1 to 1-6, 1-11 to 1-13 and 2-1 to 2-6.

Compared with the above comparative examples 1-1 to 1-15 and 2-1 to 2-10, examples 1-1 to 1-43 and 2-1 to 2-41, due to the combination of

chemical formulae

1 and 2 in the present specification, carriers, particularly holes, of the device are easily injected into the body, thereby playing a role in grasping the balance of the device, showing that the device performance can be improved as a whole.

The above-described examples 2-1 to 2-41 are the results of devices to which BD2 and the combination of

chemical formulas

1 and 2 of the present specification are applied, and it can be observed that the device balance of the combination is also excellent when various types of blue dopants are introduced.

Claims

1. An organic light emitting device comprising:

an anode;

a cathode;

a light emitting layer disposed between the anode and the cathode; and

a hole transport region including 2 or more organic layers disposed between the light emitting layer and the anode,

the organic layer in contact with the light emitting layer among the organic layers includes a compound represented by the following chemical formula 1,

the light emitting layer includes a compound represented by the following chemical formula 2:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

any one of R8 and R9 is a group represented by the following chemical formula a, a group other than a group represented by the following chemical formula a among the R8 and R9, R1 to R7, and R10 to R18, which are the same as or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or a group other than a group represented by the following chemical formula a among the R8 and R9, adjacent groups among R1 to R6, R7, and R10 to R18 are capable of bonding to each other to form a substituted or unsubstituted hydrocarbon ring,

chemical formula a

In the chemical formula a, the compound represented by the formula (a),

l1 to l3 are each an integer of 1 to 3,

when L1 is 2 or more, 2 or more L1 s may be the same or different from each other,

when L2 is 2 or more, 2 or more L2 s may be the same or different from each other,

when L3 is 2 or more, 2 or more L3 s may be the same or different from each other,

represents a site binding to R8 or R9 of the chemical formula 1,

chemical formula 2

In the chemical formula 2,

chemical formula b

In the chemical formula b, the first and second groups,

l4 is an integer from 1 to 3,

when L4 is 2 or more, 2 or more L4 s may be the same or different from each other,

represents a site binding to at least one of G1 to G10 of the chemical formula 2,

the deuterium substitution rate of chemical formula 2 is 40% to 100%.

2. The organic light emitting device according to claim 1, wherein the deuterium substitution rate of chemical formula 2 is 40% to 99%.

3. The organic light emitting device according to claim 1, wherein the deuterium substitution rate of chemical formula 1 is 1% to 100%.

4. The organic light-emitting device according to claim 1, wherein any one of R8 and R9 is a group represented by the chemical formula a, and a group other than the group represented by the chemical formula a, R1 to R7, and R10 to R18, which are the same as or different from each other, of the R8 and R9 are each independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted with deuterium or unsubstituted, or a group other than the group represented by the following chemical formula a, R1 to R6, R7, and adjacent groups among R10 to R18 in the R8 and R9 are combined with each other to form a polycyclic cyclic aromatic hydrocarbon having 6 to 20 carbon atoms.

5. The organic light emitting device of claim 1, wherein the L1-L3 are the same or different from each other, each independently being a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group of 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium or a linear or branched alkyl group of 1 to 30 carbon atoms.

6. The organic light-emitting device according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group of carbon number 6 to 30 substituted or unsubstituted with 1 or more selected from deuterium, a linear or branched alkyl group of carbon number 1 to 30 substituted with deuterium, a linear or branched alkyl group of carbon number 1 to 30, a linear or branched alkylsilyl group of carbon number 1 to 30, and a monocyclic or polycyclic aromatic group of carbon number 6 to 30; or a monocyclic or polycyclic heteroaryl group of 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more members selected from deuterium, a linear or branched alkyl group of 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms.

7. The organic light-emitting device according to claim 1, wherein at least one of G1 to G10 is a group represented by the following chemical formula b, and the others are the same as or different from each other, and are each independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more selected from deuterium and a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

8. The organic light-emitting device of claim 1, wherein L4 is a monocyclic or polycyclic arylene group of 6 to 30 carbon atoms directly bonded, or substituted or unsubstituted with deuterium.

9. The organic light-emitting device according to claim 1, wherein a and B are the same as or different from each other, and each independently is a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more selected from deuterium and a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or a monocyclic or polycyclic heterocycle of 2 to 30 carbon atoms substituted or unsubstituted with deuterium.

10. The organic light emitting device according to claim 1, wherein the chemical formula 1 is any one selected from the following compounds:

11. the organic light emitting device according to claim 1, wherein the chemical formula 2 is any one selected from the following compounds:

12. the organic light-emitting device according to claim 1, wherein an organic layer in the organic layer in contact with the anode contains a carbazole-based compound.

13. The organic light emitting device according to claim 1, wherein the organic layer comprises a hole transport layer containing the compound represented by chemical formula 1 and a hole adjusting layer.

14. The organic light emitting device according to claim 1, wherein the triplet energy of the chemical formula 1 is 2.4eV to 2.8 eV.

15. The organic light emitting device according to claim 1, wherein the light emitting layer comprises a host comprising the compound represented by chemical formula 2 and a dopant.

16. The organic light emitting device according to claim 1, wherein the light emitting layer comprises 2 or more kinds of mixed hosts, and 1 or more of the 2 or more kinds of mixed hosts comprises the compound represented by the chemical formula 2.

17. The organic light emitting device according to claim 1, wherein the light emitting layer comprises 2 or more mixed hosts, at least 1 of the 2 or more mixed hosts comprises the compound represented by chemical formula 2, and the rest comprises 1 or more selected from an anthracene-based compound not comprising deuterium as a substituent and an anthracene-based compound comprising deuterium as a substituent and different from the chemical formula 2.

18. The organic light emitting device of claim 1, wherein a maximum light emission wavelength λ of a light emission spectrum of the organic light emitting device_{Maximum of}From 400nm to 470 nm.

19. The organic light emitting device of claim 1, wherein the light emitting layer comprises a host and a dopant, the dopant being a fluorescent dopant.

20. The organic light-emitting device according to claim 1, wherein the light-emitting layer contains a host and a dopant containing 1 or more selected from a pyrene-based compound and a non-pyrene-based compound.

21. The organic light-emitting device according to claim 20, wherein the non-pyrene based compound comprises a boron based compound.

22. The organic light emitting device according to claim 1, wherein the organic light emitting device comprises an electron transport region disposed between the cathode and the light emitting layer, the electron transport region comprising a compound represented by the following chemical formula 3:

chemical formula 3

In the chemical formula 3, the first and second organic solvents,

x1 is N or Q101, X2 is N or Q102, X3 is N or Q103,

at least one of the X1 to X3 is N,

23. The organic light emitting device according to claim 22, wherein the electron transport region comprises a compound represented by the chemical formula 3, an organic alkali metal complex, and a mixture thereof.