KR102138430B1 - Organic light emitting device - Google Patents

Abstract

This specification is the first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a first compound and a second compound. to provide.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of No. 10-2017-0114012 filed with the Korean Patent Office on September 6, 2017, the entire contents of which are incorporated herein.

The present specification relates to an organic light emitting device.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet with the electrons. When it falls to the ground again, it will shine.

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

Korean Open Publication No. 10-2013-118059

The present specification provides an organic light emitting device.

This specification is the first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,

The organic layer includes a light emitting layer,

The light emitting layer provides an organic light emitting device comprising a first compound represented by the following Chemical Formula 1 and a second compound represented by any one of the following Chemical Formulas 2 to 5.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formula 1,

X1 is O or S,

L1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, or substituents in the same carbon combine with each other to form a substituted or unsubstituted spiro bond,

R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amide group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring, or substituents in the same carbon are bonded to each other to replace or unsubstituted spiro Form a bond,

m1, n1 and o1 are each independently an integer from 0 to 4,

p1 is an integer from 0 to 3,

t1 is 1 or 2,

t2 is an integer from 0 to 3,

When m1 is 2 or more, R1 is the same as or different from each other,

When n1 is 2 or more, R2 is the same as or different from each other,

When o1 is 2 or more, R3 is the same as or different from each other,

When p1 is 2 or more, R4 is the same as or different from each other,

When t1 is 2, structures in parentheses are the same or different from each other,

When t2 is 2 or more, L1 is the same as or different from each other,

In Chemical Formulas 2 to 5,

X ₂ to X ₄ are the same or different, each independently N or CR'R'',

R5 to R22, R7', R'and R'' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Or NRaRb, or may combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heteroring,

R21 and R22 are each bonded to a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring,

Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group,

L2 to L5 are the same as or different from each other, and each independently a direct bond; A divalent phosphine oxide group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroaryl group,

m2 and n2 are each independently an integer from 0 to 4,

u1 is an integer from 1 to 5,

u2 is an integer from 0 to 5,

u3 is an integer from 0 to 5,

u3' is an integer from 0 to 4,

u1+u2+u3≤6,

u1+u2+u3'≤5,

When m2 is 2 or more, R5 is the same as or different from each other,

When n2 is 2 or more, R6 is the same as or different from each other,

When u3 is 2 or more, R7 is the same as or different from each other,

When u3' is 2 or more, R7' is the same or different from each other.

The organic light emitting diode according to an exemplary embodiment of the present specification can improve the efficiency, improve the low driving voltage and / or life characteristics.

The organic light emitting diode according to an exemplary embodiment of the present specification is capable of adjusting the triplet energy of the host and the energy levels of HOMO and LUMO, and it is possible to improve efficiency and improve life characteristics in combination with an appropriate dopant compound.

FIG. 1 shows an example of an organic light emitting device including a substrate 1, a first electrode 2, an organic material layer 3, and a second electrode 4.
2 is an organic light emitting device comprising a substrate 1, a first electrode 2, a hole injection layer 31, a hole transport layer 32, a light emitting layer 33, an electron transport layer 34, and a second electrode 4 It is an example of.

Hereinafter, the present specification will be described in more detail.

This specification is the first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the first compound represented by Formula 1 and the Formulas 2 to 5 above. It provides an organic light emitting device comprising a second compound represented by any one. When the delayed fluorescent host represented by Chemical Formula 1 is used in the light emitting layer of the organic light emitting device, not only the efficiency of the organic light emitting device is improved, but also has a low driving voltage and has excellent lifespan characteristics.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

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

In the present specification, the first compound may be a “delayed fluorescent host”.

In the present specification, the second compound may be a “thermal stabilization delaying compound”. In the present specification, the thermal stabilization delay compound means a thermally activated delayed fluorescence (TADF) compound.

In the present specification, the second compound may be used as a dopant in the light emitting layer. In this case, the life and efficiency of the device can be improved. The second compound is included in the light-emitting layer and exhibits delayed fluorescence properties. In general, excitons in a triplet excited state are reverse-transitioned to a singlet excited state to transfer their energy as a dopant, resulting in high efficiency. It is possible to implement an organic light emitting device having a. Particularly, when the first compound is included as a host in the light emitting layer, and the second compound is included as a dopant, energy can be better transmitted and efficiency is increased.

As used herein, "delayed fluorescent host" means a host in which a transition from a triplet excited state to a singlet excited state occurs due to crossing between inverses or the like.

Inverse crossing in the present specification refers to a non-radiative process that changes from a triplet excited state to a singlet excited state.

In the present specification, the term "single-phase excited state" means an electronic state in which the quantum number S of all spin angular motions becomes zero.

In the present specification, the term "triplet excitation state" means an electronic state in which the sum of the quantum numbers of the spin angular momentum (synthetic spin angular momentum quantum number S) of the entire electron is 1.

1 and 2 are cross-sectional views schematically showing a structure of an organic light emitting device according to an exemplary embodiment of the present specification.

The organic light emitting device according to the exemplary embodiment of the present specification includes a substrate 1, a first electrode 2, a second electrode 4 facing the first electrode 2, and the first electrode 2 and An organic material layer 3 included between the second electrodes 4 is included, and the organic material layer includes a light emitting layer.

The first electrode 2 may be an anode to which a (+) voltage is applied, and the second electrode 4 may be a cathode to which a (-) voltage is applied. Conversely, the first electrode may be a cathode and the second electrode may be an anode. For convenience, a description will be given focusing on the case where the first electrode is the anode and the second electrode is the cathode.

When a voltage is applied to the first electrode 2 and the second electrode 4, holes in the organic material layer are transported by the hole transporting material and electrons are transported by the electron transporting material to generate excitons in the excited state in the light emitting layer.

Meanwhile, the organic material layer 3 may include a hole injection layer 31 and a hole transport layer 32 between the light emitting layer 33 and the first electrode 2, and the light emitting layer 33 and the second electrode 4 An electron transport layer 34 may be included therebetween. The hole transport layer is a region related to injection and transport of holes from the anode to the light emitting layer, and the electron transport layer is a region related to injection and transport of electrons from the cathode to the light emitting layer.

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

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

In this specification, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester groups; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In one embodiment of the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In one embodiment of the present specification, the ester group may be substituted with straight or branched or cyclic alkyl groups having 1 to 25 carbon atoms or aryl groups having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In one embodiment of the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In one embodiment of the present specification, the amide group may be substituted with nitrogen of the amide group for hydrogen, a straight chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In one embodiment of the present specification, the alkyl group may be a straight chain or a branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specific examples include methyl groups; Ethyl group; Propyl group; n-propyl group; Isopropyl group; Butyl group; n-butyl group; Isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl 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; 3,3-dimethylbutyl group; 2-ethylbutyl group; Heptyl group; n-heptyl group; 1-methylhexyl group; Cyclopentyl methyl group; Cyclohexylmethyl group; Octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; Isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but is not limited thereto.

In one embodiment of the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; Cyclobutyl group; Cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; Cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; Cycloheptyl group; Cyclooctyl group, and the like, but is not limited thereto.

In one embodiment of the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specifically, a methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; p-methylbenzyloxy group, and the like, but is not limited thereto.

In one embodiment of the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl groups; 1-propenyl group; Isopropenyl group; 1-butenyl group; 2-butenyl group; 3-butenyl group; 1-pentenyl group; 2-pentenyl group; 3-pentenyl group; 3-methyl-1-butenyl group; 1,3-butadienyl group; Allyl group; 1-phenylvinyl-1-yl group; 2-phenylvinyl-1-yl group; 2,2-diphenylvinyl-1-yl group; 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group; 2,2-bis(diphenyl-1-yl)vinyl-1-yl group; Steel benyl group; Styrene group and the like, but is not limited thereto.

In one embodiment of the present specification, the silyl group may be represented by the formula of -SiR ₁₀₀ R ₁₀₁ R ₁₀₂ , wherein R ₁₀₀ , R ₁₀₁ and R ₁₀₂ are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyl dimethyl silyl group; Propyl dimethyl silyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but is not limited thereto.

In one embodiment of the present specification, the boron group may be -BR ₁₀₃ R ₁₀₄ , wherein R ₁₀₃ and R ₁₀₄ are the same or different, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methyl anthracenylamine group; Diphenylamine group; N-phenyl naphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenyl fluorenylamine group, and the like, but is not limited thereto.

In one embodiment of the present specification, the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

In an exemplary embodiment of the present specification, the N-aryl heteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.

In one embodiment of the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In one embodiment of the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the above-described alkyl group. Specifically, an alkyl thioxy group is a methyl thioxy group; Ethyl thioxy group; tert-butyl thioxy group; Hexyl thioxy group; And octyl thiooxy groups, and alkyl sulfoxy groups include mesyl; Ethyl sulfoxyl group; Profiling; Butyl sulfoxyl group, but is not limited thereto.

In one embodiment of the present specification, the phosphine oxide group is specifically a diphenylphosphine oxide group; A dinaphthylphosphine oxide group, but is not limited thereto.

In one embodiment of the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic.

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

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, a polycyclic aryl group is a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group and the like, but is not limited thereto.

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

,

,

,

,

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

,

And

It can be back. However, it is not limited thereto.

In one embodiment of the present specification, the “adjacent” group is a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituted in the atom substituted by the substituent. It may mean a substituent. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In one embodiment of the present specification, the aryl group in the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the N-aryl alkylamine group, the N-aryl heteroarylamine group, and the arylphosphine group are the same as those of the above-described aryl group. . Specifically, as the aryloxy group, a phenoxy group; p-tolyloxy group; m-tolyloxy group; 3,5-dimethylphenoxy group; 2,4,6-trimethylphenoxy group; p-tert-butylphenoxy group; 3-biphenyloxy group; 4-biphenyloxy group; 1-naphthyloxy group; 2-naphthyloxy group; 4-methyl-1-naphthyloxy group; 5-methyl-2-naphthyloxy group; 1-anthryloxy group; 2-anthryloxy group; 9-anthryloxy group; 1-phenanthryloxy group; 3-phenanthryloxy group; And 9-phenanthryloxy groups, and examples of the arylthioxy group include a phenylthioxy group; 2-methylphenyl thioxy group; 4-tert-butylphenyl thioxy group and the like, and aryl sulfoxy group is benzene sulfoxy group; p-toluene sulfoxyl group, but is not limited thereto.

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

In the exemplary embodiment of the present specification, the heteroaryl group includes one or more non-carbon atoms, that is, heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of O, N, Se, and S. can do. The number of carbon atoms is not particularly limited, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrol group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazole group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline group (phenanthroline); Isooxazolyl group; Thiadiazolyl group; Phenothiazinyl group and dibenzofuranyl group, and the like, but is not limited thereto.

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

In one embodiment of the present specification, examples of the heteroaryl group in the N-aryl heteroarylamine group and the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

In an exemplary embodiment of the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.

In one embodiment of the present specification, the heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.

) 및 술포닐기를 포함하는 헤테로고리 구조, 예컨대,

,

등이 있다.In one embodiment of the present specification, the heterocyclic ring may be monocyclic or polycyclic, aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group. Other examples of heterocycles include hydroacrylyl groups (e.g.,

) And sulfonyl groups, including heterocyclic structures, such as

,

And so on.

In one embodiment of the present specification, in the substituted or unsubstituted ring formed by adjacent groups being bonded to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or substituted or unsubstituted heterocyclic ring.

In one embodiment of the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group, except for the non-monovalent.

In an exemplary embodiment of the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group, except that it is not monovalent.

In the exemplary embodiment of the present specification, the heterocycle contains one or more non-carbon atoms, heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of O, N, Se, and S. can do. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group or heterocyclic group except for non-monovalent.

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 4 to 20 carbon atoms.

In one embodiment of the present specification, L1 combines substituents in the same carbon with each other to form a substituted or unsubstituted spiro bond.

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

In one embodiment of the present specification, L1 is a substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted fluorenylene group.

In one embodiment of the present specification, L1 is any one of the following structures substituted or unsubstituted.

를 의미하고,In the above structural formula, A is of formula 1

Means,

를 의미한다.B is of Formula 1

Means

In one embodiment of the present specification, L1 is a biphenylene group unsubstituted or substituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group; Or a fluorenylene group unsubstituted or substituted with a cyano group, an alkyl group, an aryl group, or a heteroaryl group.

In one embodiment of the present specification, L1 is a biphenylene group unsubstituted or substituted with a cyano group or a heteroaryl group; Or a fluorenylene group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group.

In one embodiment of the present specification, L1 is a cyano group or a biphenylene group unsubstituted or substituted with a 6 to 20 carbon atoms heteroaryl group; Or a fluorenylene group unsubstituted or substituted with a cyano group, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, L1 is a biphenylene group unsubstituted or substituted with a cyano group or a carbazole group; Or a fluorenylene group unsubstituted or substituted with a cyano group, a methyl group or a phenyl group.

In one embodiment of the present specification, L1 is a biphenylene group substituted with a cyano group.

In one embodiment of the present specification, L1 is a biphenylene group substituted with a carbazole group.

In one embodiment of the present specification, L1 is a biphenylene group.

In one embodiment of the present specification, L1 is a fluorenylene group substituted with a cyano group.

In one embodiment of the present specification, L1 is a fluorenylene group substituted with a methyl group.

,

및

중에서 선택될 수 있고,

는 주쇄와 연결되는 부위와 결합하는 것를 의미한다.In one embodiment of the present specification, L1 is substituted or unsubstituted with a cyano group or a methyl group

,

And

Can be selected from

Means binding to a site connected to the main chain.

In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1A to 1D.

[Formula 1A]

[Formula 1B]

[Formula 1C]

[Formula 1D]

In the formulas 1A to 1D, the description of the substituent is as in the formula (1).

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Cyano group; A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Or a substituted or unsubstituted silyl group; It is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Cyano group; Methyl group; Ethyl group; Propyl group; t-butyl group; A silyl group unsubstituted or substituted with a methyl group having 1 to 4 carbon atoms; Phenyl group; Or a biphenyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Cyano group; Methyl group; t-butyl group; Trimethylsilane group; Phenyl group; Or a biphenyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Cyano group; Or a phenyl group.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; It is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R3 is hydrogen; Cyano group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R3 is hydrogen; Cyano group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen; Cyano group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R3 is hydrogen; Cyano group; Or a phenyl group.

In one embodiment of the present specification, R4 is hydrogen.

는 아래 화학식 중 어느 하나로 표시될 수 있다.In one embodiment of the present specification, Chemical Formula 1

Can be represented by any of the following formula.

In the above structural formula, Y ₁ is O, S or NR _x R _y ,

The definitions of R1', R2', R12', R _x and R _y are the same as the definitions of R1 to R4 above,

m1' and n1' are each an integer of 0 to 4,

mn1 is an integer from 0 to 2,

When m1' is 2 or more, R1' is the same as or different from each other,

When n1' is 2 or more, R2' is the same as or different from each other,

When mn1 is 2, R12' is the same as or different from each other,

은 화학식 1의 L1에 결합하는 부위를 의미한다.

Means a site that binds to L1 in Formula 1.

는 아래 화학식 중 어느 하나로 표시될 수 있다.In one embodiment of the present specification, Chemical Formula 1

Can be represented by any of the following formula.

And In the above formula, Y ₂ is O, S, or NR _x 'R _y',

The definition of R4', R _x 'and R _y ' is the same as the definition of R1 to R4 above,

o1 is an integer from 0 to 4,

p1' is an integer from 0 to 5,

When o1 is 2 or more, R3 is the same as or different from each other,

When p1' is 2 or more, R4' is the same as or different from each other,

은 화학식 1의 L1에 결합하는 부위를 의미한다.

Means a site that binds to L1 in Formula 1.

In one embodiment of the present specification, t1 is 1.

In one embodiment of the present specification, t1 is 2, and structures in parentheses are the same or different from each other.

In one embodiment of the present specification, t2 is 1.

In one embodiment of the present specification, t2 is 2 or 3, and L1 is the same as or different from each other.

In one embodiment of the present specification, the second compound is represented by any one of Formulas 2 to 5.

In one embodiment of the present specification, X ₂ to X ₄ are the same or different, and each independently N or CR'R''.

In one embodiment of the present specification, X ₂ is N, and X ₃ and X ₄ are the same or different, and each independently CR'R''.

In one embodiment of the present specification, X ₂ and X ₃ are N, and X ₄ is CR'R''.

In one embodiment of the present specification, X ₃ is N, and X ₂ and X ₄ are the same or different, and each independently CR'R''.

In one embodiment of the present specification, X ₂ to X ₄ are N.

In one embodiment of the present specification, R5 to R22, R7', R'and R'' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R5 to R22, R7', R'and R'' are the same as or different from each other, and each independently hydrogen; Fluorine group; Cyano group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted methyl group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R5 to R22, R7', R'and R'' are the same as or different from each other, and each independently hydrogen; Fluorine group; Cyano group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted methyl group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R5 to R22, R7', R'and R'' are the same as or different from each other, and each independently hydrogen; Fluorine group; Cyano group; Phenyl group; A triazine group unsubstituted or substituted with an aryl group having 6 to 12 carbon atoms; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R5 to R22, R7', R'and R'' are the same as or different from each other, and each independently hydrogen; Fluorine group; Cyano group; Phenyl group; A triazine group unsubstituted or substituted with a phenyl group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R'and R'' are hydrogen.

In one embodiment of the present specification, R5 to R9 and R7' are the same as or different from each other, and each independently hydrogen; Cyano group; Fluorine group; An alkyl group having 1 to 6 carbon atoms unsubstituted or substituted with an alkyl group; An aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, R5 to R9 and R7' are the same as or different from each other, and each independently hydrogen; Cyano group; Fluorine group; Methyl group; t-butyl group; A phenyl group unsubstituted or substituted with an alkyl group; Biphenyl group; Or a carbazole group unsubstituted or substituted with an aryl group.

In one embodiment of the present specification, R5 to R9 and R7' are the same as or different from each other, and each independently hydrogen; Cyano group; Fluorine group; Methyl group; t-butyl group; A phenyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; Biphenyl group; Or a carbazole group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R5 to R9 and R7' are the same as or different from each other, and each independently hydrogen; Cyano group; Fluorine group; Methyl group; t-butyl group; A phenyl group unsubstituted or substituted with a methyl group; Biphenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.

In one embodiment of the present specification, R10 to R12 are the same as or different from each other, and each independently hydrogen; Fluorine group; Cyano group; Phenyl group; A triazine group unsubstituted or substituted with a phenyl group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R10 to R12 are the same as or different from each other, and each independently hydrogen; Phenyl group; A carbazole group unsubstituted or substituted with an aryl group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R10 to R12 are the same as or different from each other, and each independently hydrogen; Phenyl group; A carbazole group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R10 to R12 are the same as or different from each other, and each independently hydrogen; Phenyl group; A carbazole group unsubstituted or substituted with a phenyl group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R13 to R22 are the same as or different from each other, and each independently hydrogen; Cyano group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R21 and R22 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or it may form a substituted or unsubstituted heterocycle.

In one embodiment of the present specification, R13 to R22 are the same as or different from each other, and each independently hydrogen; Cyano group; A phenyl group unsubstituted or substituted with a cyano group; Or NRaRb, and Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ra and Rb are hydrogen; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, the NRaRb may be represented by any one of the following Chemical Formulas 6 to 12.

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In one embodiment of the present specification, R25 to R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Or a substituted or unsubstituted alkenyl group having 1 to 4 carbon atoms, R27 and R28 may combine with each other to form a hydrocarbon ring or a heterocycle.

In one embodiment of the present specification, R25 to R31 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted methyl group; A substituted or unsubstituted t-butyl group; Or a substituted or unsubstituted vinyl group, R27 and R28 may combine with each other to form a hydrocarbon ring or a heterocycle.

In one embodiment of the present specification, R25 to R31 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; A phenyl group unsubstituted or substituted with a methyl group or a cyano group; Biphenyl group; A carbazole group unsubstituted or substituted with a phenyl group; Methyl group; t-butyl group; Or a cyano group substituted or unsubstituted vinyl group, R27 and R28 may be bonded to each other to form a hydrocarbon ring or a heterocycle.

In one embodiment of the present specification, R25 to R31 are the same as or different from each other, and each independently hydrogen; Halogen group; Cyano group; A phenyl group unsubstituted or substituted with a methyl group or a cyano group; Biphenyl group; A carbazole group unsubstituted or substituted with a phenyl group; Methyl group; t-butyl group; Or a vinyl group substituted with a cyano group, R27 and R28 may combine with each other to form a hydrocarbon ring or a heterocycle.

In one embodiment of the present specification, R25 and R26 are the same as or different from each other, and each independently hydrogen; Or a methyl group.

In one embodiment of the present specification, R30 and R31 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R30 and R31 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R30 and R31 are phenyl groups.

q and r are each independently an integer from 0 to 4.

s is an integer from 0 to 2.

When q is 2 or more, R25 is the same as or different from each other.

When r is 2 or more, R26 is the same as or different from each other.

When s is 2, R29 is the same or different from each other.

In one embodiment of the present specification, L2 to L5 are the same as or different from each other, and each independently a direct bond; A divalent phosphine oxide group; A substituted or unsubstituted arylene group; Or it may be a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L2 to L4 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or it may be a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L2 to L4 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or it may be a carbazole group.

In one embodiment of the present specification, L2 to L4 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or it may be a carbazole group.

In one embodiment of the present specification, L5 is a direct bond; Or a divalent phosphine oxide group.

In one embodiment of the present specification, the energy level difference (ΔEst) between the lowest triplet state (T1) and the singlet excited state (S1) of the second compound may be 0.3 eV or less, preferably 0.2 eV or less . The difference in energy levels between the lowest triplet state (T1) and the singlet excitation state (S1) of the thermal stabilization delay compound may be small, so that the inverse crossover from the triplet state to the singlet excitation state may be facilitated.

In the present specification, the second compound is a thermal stabilization delay compound.

The singlet excitation state of the first compound generated by the increase of the inverse crossing can transfer energy to the second compound. Due to the energy transfer, more of the second compound in the singlet excited state may be generated, thereby increasing the fluorescence emission efficiency.

In the present specification, HOMO (highest occupied molecular orbital) means a molecular orbital function (highest occupied molecular orbital) in the region with the highest energy in the region where electrons can participate in binding, and LUMO (lowest unoccupied molecular orbital). Column means a molecular orbital function (lowest unoccupied molecular orbital) in which the electron is in the lowest energy region of the semi-bonding region, and the HOMO energy level means the distance from the vacuum level to the HOMO. In addition, LUMO energy level means the distance from a vacuum level to LUMO.

In one embodiment of the present specification, the thermal stabilization delay compound has a singlet energy of 2.0eV to 3.2eV, a triplet energy of 2.1eV to 3.3eV, and a HOMO energy level of 4.5eV. To 6.0eV, LUMO energy level may be 1.8eV to 3.0eV, but is not limited thereto.

In one embodiment of the present specification, a bandgap means a difference in energy levels between HOMO and LUMO, that is, a HOMO-LUMO gap.

In one embodiment of the present specification, HOMO and LUMO energy levels and energy of the lowest triplet state (T1) and the lowest excited singlet state (S1) of each compound are calculated through quantum chemical calculations.

In one embodiment of the present specification, the lowest triplet state T1 is the energy of the triplet state with the lowest energy.

In one embodiment of the present specification, the lowest excited singlet state S1 is the energy of the singlet state having the lowest energy.

In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds.

In one embodiment of the present specification, the second compound may be one of the following compounds.

In one embodiment of the present specification, the light emitting layer further includes a phosphorescent dopant.

In one embodiment of the present specification, the phosphorescent dopant is an iridium complex.

In one embodiment of the present specification, the content of the second compound is greater than the content of the phosphorescent dopant.

In one embodiment of the present specification, the phosphorescent dopant may be any one of the following structures, but is not limited thereto.

In one embodiment of the present specification, the light emitting layer of the organic light emitting device is 0.01 to 50 parts by weight, preferably 0.01 to 30 parts by weight, more preferably 1 to 100 parts by weight of the first compound To 20 parts by weight.

In one embodiment of the present specification, the light emitting layer of the organic light emitting device is 0.01 to 5 parts by weight of the phosphorescent dopant based on 100 parts by weight of the first compound, preferably 0.01 to 3 parts by weight, more preferably 0.1 to 2 parts by weight.

In one embodiment of the present specification, the first compound and the second compound may be prepared by materials and methods known in the art.

In one embodiment of the present specification, the first compound represented by Chemical Formula 1 may be prepared by a manufacturing method described later. For example, the compound of Formula 1 may have a core structure as shown in the following scheme. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art. Reaction types and reaction conditions may be those known in the art.

In the above reaction formula, Y10 to Y30 are the same as or different from each other, and may be chlorine, bromine or iodine, respectively.

The definition of the remaining substituents in the above reaction formula is as in Formula 1.

In one embodiment of the present specification, the organic material layer further includes at least one selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a hole blocking layer.

In one embodiment of the present specification, the organic light emitting device may have the structures (1) to (10) below.

(1) substrate/first electrode/light emitting layer/second electrode;

(2) substrate/first electrode/hole injection layer/light emitting layer/second electrode;

(3) substrate/first electrode/hole transport layer/light emitting layer/second electrode;

(4) substrate/first electrode/hole injection layer/hole transport layer/light emitting layer/second electrode;

(5) substrate/first electrode/light emitting layer/electron transport layer/second electrode;

(6) substrate/first electrode/light emitting layer/electron injection layer/second electrode;

(7) substrate/first electrode/light emitting layer/hole blocking layer/second electrode;

(8) substrate/first electrode/light emitting layer/electron transport layer/electron injection layer/second electrode;

(9) substrate/first electrode/light emitting layer/hole blocking layer/electron transport layer/second electrode;

(10) A substrate/first electrode/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/second electrode, etc. may have a structure. And sequentially stacking the second electrodes. At this time, an anode is formed by depositing metal or conductive metal oxides or alloys thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And, it can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, a light emitting layer may be formed by a vacuum coating method as well as a solution coating method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

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

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole is transported to the light emitting layer by transporting holes from an anode or a hole injection layer, and the mobility of holes is large. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons This is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

The hole blocking layer is a layer that prevents the cathode from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.

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

<Synthesis example>

Synthesis Example 1: Synthesis of Compound 1

Intermediate 1-1 Intermediate 1-2 Compound 1

Intermediate 1-1 3.9 g (12.0 mmol), Intermediate 1-2 5.4 g (12.0 mmol), 2M K ₂ CO ₃ aqueous solution 12 mL (24.0 mmol), tetrahydrofuran 50 mL, 5 mol% Pd (PPh ₃ ) ₄ (Tetrakis(triphenylphosphine)palladium(0)) 0.58 g (0.5 mmol) was added, and the mixture was refluxed and stirred for 8 hours under a nitrogen atmosphere. After the reaction was completed, the mixture was cooled to room temperature, 50 mL of distilled water was added, and extracted with chloroform (CHCl ₃ ). After drying over anhydrous magnesium sulfate, filtered and concentrated. Next, it was purified by column chromatography (hexane: methylene chloride = volume ratio of 4:1). After drying, compound 1 (4.53 g, yield 58%) was obtained. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=650.

Synthesis Example 2: Synthesis of Compound 2

Intermediate 2-1 Intermediate 2-2 Compound 2

Intermediate 2-1 3.87 g (10.0 mmol), Intermediate 2-2 2.87 g (12.0 mmol), 2M K ₂ CO ₃ aqueous solution 10 mL (20.0 mmol), tetrahydrofuran 50 mL, 5 mol% Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) was added, and the mixture was refluxed and stirred under a nitrogen atmosphere for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, 50 mL of distilled water was added, and extracted with chloroform (CHCl ₃ ). After drying over anhydrous magnesium sulfate, filtered and concentrated. Next, it was purified by column chromatography (hexane:ethyl acetate = 1:1 volume ratio). After drying, compound 2 (3.10 g, yield 64%) was obtained. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=485.

Synthesis Example 3: Synthesis of Compound 3

Intermediate 2-1 Intermediate 1-2 Compound 3

Intermediate 2-1 3.9 g (12.0 mmol), Intermediate 1-2 5.4 g (12.0 mmol), 2M K ₂ CO ₃ aqueous solution 12 mL (24.0 mmol), tetrahydrofuran 50 mL, 5 mol% Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) was added, and the mixture was refluxed and stirred under a nitrogen atmosphere for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, 50 mL of distilled water was added, and extracted with chloroform (CHCl ₃ ). After drying over anhydrous magnesium sulfate, filtered and concentrated. Next, it was purified by column chromatography (hexane:methylene chloride = volume ratio of 4:1). After drying, compound 3 (4.68 g, yield 60%) was obtained. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=650.

Synthesis Example 4: Synthesis of Compound 4

Intermediate 1-1 Intermediate 2-2 Compound 4

Intermediate 1-1 7.74 g (20.0 mmol), Intermediate 2-2 5.74 g (24.0 mmol), 2M K ₂ CO ₃ aqueous solution 20 mL (40.0 mmol), tetrahydrofuran 100 mL, 5 mol% Pd (PPh ₃ ) ₄ 1.6 g (1.0 mmol) was added, and the mixture was refluxed and stirred under a nitrogen atmosphere for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, 100 mL of distilled water was added, and extracted with chloroform (CHCl ₃ ). After drying over anhydrous magnesium sulfate, filtered and concentrated. Next, it was purified by column chromatography (hexane:ethyl acetate = 1:1 volume ratio). After drying, compound 4 (6.40 g, yield 66%) was obtained. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=485.

Synthesis Example 5: Synthesis of Compound 5

1) Synthesis of Intermediate 5-1

Intermediate 5-1

Dibenzo[b,d]furan-1-ylboronic acid 4.2 g (20.0 mmol), 3-bromo-5-iodo benzonitrile 6.5 g (21.0 mmol) and potassium carbonate 8.3 g (60.0 mmol) are tetrahydrofuran 100 It was dissolved in a mixed solvent of 30 mL of distilled water, and 0.6 g (0.5 mmol) of Pd(PPh ₃ ) ₄ was added and refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, it was purified by column chromatography to obtain Intermediate 5-1 (2.5 g, yield 36.4%).

2) Synthesis of Compound 5

Intermediate 5-1 Intermediate 2-2 Compound 5

Intermediate 5-1 2.53 g (7.3 mmol), intermediate 2-2 2.30 g (8.0 mmol), 2M K ₂ CO ₃ aqueous solution 10 mL (20.0 mmol), tetrahydrofuran 50 mL, 5 mol% Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) was added, and the mixture was refluxed and stirred under a nitrogen atmosphere for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, 50 mL of distilled water was added, and extracted with chloroform (CHCl ₃ ). After drying over anhydrous magnesium sulfate, filtered and concentrated. Next, it was purified by column chromatography (hexane:ethyl acetate = 1:2). After drying, compound 5 (1.86 g, yield 50%) was obtained. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=510.

Synthesis Example 6: Synthesis of Compound 6

1) Synthesis of Intermediate 6-1

Intermediate 6-1

Dibenzo[b,d]furan-4-ylboronic acid 4.2 g (20.0 mmol), 3-bromo-5-iodo benzonitrile 6.5 g (21.0 mmol), potassium carbonate 8.3 g (60.0 mmol) tetrahydrofuran 100 It was dissolved in a mixed solvent of 30 mL of distilled water, and 0.6 g (0.5 mmol) of Pd(PPh ₃ ) ₄ was added and refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, it was purified by column chromatography to obtain intermediate 6-1 (2.4 g, yield 34.6%).

2) Synthesis of Compound 6

Intermediate 6-1 Intermediate 2-2 Compound 6

Intermediate 6-1 2.53 g (7.3 mmol), intermediate 2-2 2.30 g (8.0 mmol), 2M K ₂ CO ₃ aqueous solution 10 mL (20.0 mmol), tetrahydrofuran 50 mL, 5 mol% Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) was added, and the mixture was refluxed and stirred under a nitrogen atmosphere for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, 50 mL of distilled water was added, and extracted with chloroform (CHCl ₃ ). After drying over anhydrous magnesium sulfate, filtered and concentrated. Next, it was purified by column chromatography (hexane:methylene chloride = 2:1). After drying, compound 6 (1.79 g, yield 48%) was obtained. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=510.

Synthesis Example 7: Synthesis of Compound 7

1) Synthesis of Intermediate 7-1

Intermediate 1-1 Intermediate 7-1

Intermediate 1-1 6.5 g (20 mmol), bis(pinacholate)diboron 6.6 g (26.0 mmol), [1,1-bis(diphenylphosphino)ferrocene]dicolopalladium(II) 1.1 g(1.5 mmol) and toluene (40 mL) and stirred under reflux. After the reaction was completed, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure, and separated into a column. Did.

2) Synthesis of Compound 7

Intermediate 7-1 Intermediate 7-2 Compound 7

4.4 g (12.0 mmol) of compound 7-1, 5.9 g (12.0 mmol) of compound 7-2, and 5.0 g (36 mmol) of potassium carbonate were dissolved in a mixed solvent of tetrahydrofuran and 300 mL of distilled water, and Pd (PPh ₃ ) ₄ 1.4 g (1.2 mmol) was added and refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration and purification by column chromatography, compound 7 (5.5 g, yield 70.4%) was prepared. As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=650.

Synthesis Example 8: Synthesis of Compound 8

1) Synthesis of Intermediate 8-1

Intermediate 6-1 Intermediate 8-1

Intermediate 6-1 7.0 g (20 mmol), bis(pinacholate)diboron 6.6 g (26.0 mmol), [1,1-bis(diphenylphosphino)ferrocene]dicolopalladium(II) 1.1 g(1.5 mmol) and toluene (40 mL) and stirred under reflux. After the reaction was completed, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure, and separated into a column. The obtained developing solution was concentrated under reduced pressure, crystallized with hexane, and filtered to obtain intermediate 8-1 (5.8 g, yield 74%). Did.

2) Synthesis of Compound 8

Intermediate 8-1 Intermediate 7-2 Compound 8

4.7 g (12.0 mmol) of compound 8-1, 5.9 g (12.0 mmol) of compound 7-2, and 5.0 g (6 mmol) of potassium carbonate were dissolved in a mixed solvent of tetrahydrofuran (100 mL) and 300 mL of distilled water, and Pd (PPh ₃ ) ₄ 1.4 g (1.2 mmol) was added and refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, purified by column chromatography to prepare compound 8 (5.3 g, yield 65.2%). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=675.

Synthesis Example 9: Synthesis of Compound 9

1) Synthesis of Intermediate 9-1

Intermediate 9-1

5.0 g (24.05 mmol) of 1-bromo-3-chloro-5-fluorobenzene, 4.01 g (24.05 mmol) of 9H-carbazole and 15.7 g (48.1 mmol) of Cesium carbonate were added to Dimethylformamide (50 ml) and stirred at reflux. After completion of the reaction, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure, separated into a column, and the obtained developing solution was concentrated under reduced pressure, crystallized with hexane, and filtered to obtain intermediate 9-1 (6.2 g, yield 73%). Did.

2) Synthesis of Intermediate 9-2

Intermediate 9-1 Intermediate 9-2

6.2 g (17.47 mmol) of Intermediate 9-1, 1.23 g (10.48 mmol) of Zinc Cyanide and 2.08 g (1.8 mmol) of Pd(PPh ₃ ) ₄ were added and refluxed for 6 hours. After the reaction was completed, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure, and separated into a column. The obtained developing solution was concentrated under reduced pressure, crystallized with hexane, and filtered to obtain intermediate 9-2 (3.6 g, yield 68%). Did.

3) Synthesis of Compound 9

Intermediate 9-2 Intermediate 7-1 Compound 9

3.6 g (11.92 mmol) of intermediate 9-2 and 4.4 g (11.92 mmol) of intermediate 7-1 were dissolved in 60 ml of tetrahydrofuran, and mixed with a solution of 4.9 g (35.76 mmol) of potassium carbonate dissolved in 30 ml of distilled water and stirred. After adding 1.4 g (1.2 mmol) of Pd(PPh ₃ ) ₄ to the mixture, it was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, purified by column chromatography to prepare compound 9 (4.7 g, yield 77%). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=510.

Synthesis Example 10: Synthesis of Compound 10

1) Synthesis of Intermediate 10-1

Intermediate 10-1

9H-carbazole-3-carbonitrile 5.0 g (26.03 mmol), 1-chloro-3-fluorobenzene 3.4 g (26.03 mmol) and Cesium carbonate 16.9 g (52.06 mmol) were added to Dimethylformamide (50 ml) and stirred at reflux. After the reaction was completed, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure and separated into a column, and then the obtained developing solution was concentrated under reduced pressure, crystallized with hexane, and filtered to obtain intermediate 10-1 (5.4 g, yield 69%). Did.

2) Synthesis of Compound 10

Intermediate 7-1 Intermediate 10-1 Compound 10

6.6 g (17.87 mmol) of Intermediate 7-1, 5.4 g (17.87 mmol) of Intermediate 10-1 was dissolved in 60 ml of tetrahydrofuran, and 7.4 g (53.61 mmol) of potassium carbonate was dissolved in 30 ml of distilled water and stirred. After adding 1.9 g (1.7 mmol) of Pd(PPh ₃ ) ₄ thereto, the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, purified by column chromatography to prepare compound 10 (6.4 g, yield 71%). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=510.

Synthesis Example 11: Synthesis of Compound 11

1) Synthesis of Intermediate 11-1

Intermediate 11-1

2-phenyl-9H-carbazole 5 g (20.57 mmol), 1-chloro-3-fluorobenzene 2.7 g (20.57 mmol) and Cesium carbonate 13.4 g (41.14 mmol) were added to Dimethylformamide (50 ml) and stirred at reflux. After the reaction was completed, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure and separated into a column, and then the obtained developing solution was concentrated under reduced pressure, crystallized with hexane, and filtered to obtain intermediate 11-1 (4.8 g, yield 67%). Did.

2) Synthesis of Compound 11

Intermediate 7-1 Intermediate 11-1 Compound 11

5 g (13.59 mmol) of intermediate 7-1, 4.8 g (13.59 mmol) of intermediate 11-1 were dissolved in 50 ml of tetrahydrofuran, and 5.6 g (40.77 mmol) of potassium carbonate was dissolved in 25 ml of distilled water and stirred. After adding 1.5 g (1.3 mmol) of Pd(PPh ₃ ) ₄ to the mixture, it was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, purified by column chromatography to prepare compound 11 (5.3 g, yield 70%). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=561.

Synthesis Example 12: Synthesis of Compound 12

1) Synthesis of Intermediate 12-1

Intermediate 12-1

2-bromo-7-iodo-9,9-dimethyl-9H-fluorene 5 g (12.56 mmol), dibenzo[b,d]furan-1-ylboronic acid 2.7 g (12.56 mmol) dissolved in 50 ml of tetrahydrofuran, carbonated Potassium 5.2 g (37.68 mmol) was mixed with a solution dissolved in 25 ml of distilled water and stirred. After adding 1.4 g (1.2 mmol) of Pd(PPh ₃ ) ₄ to the mixture, it was refluxed for 12 hours. After cooling to room temperature, the water layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, purified by column chromatography to obtain intermediate 12-1 (3.5 g, yield 64%).

2) Synthesis of Compound 12

Intermediate 12-1 Compound 12

3.5 g (7.99 mmol) of intermediate 12-1, 1.9 g (7.99 mmol) of 2-phenyl-9H-carbazole and 1.2 g (11.98 mmol) of sodium t-butoxide were dissolved in 35 ml of toluene and Pd(t-Bu ₃ P) ₂ 0.04 g (0.08 mmol) was added and refluxed for 6 hours. Upon completion of the reaction, the reaction solution was filtered through silica gel/celite, concentrated under reduced pressure, and purified by column chromatography to prepare compound 12 (3.8 g, yield 80%). As a result of the mass spectrum measurement of the obtained solid, a peak was confirmed at M/Z=601.

<Experimental Example>

[Example 1]

Example 1-1: Preparation of an organic light emitting device to which the compound 1 is applied

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

On this prepared ITO transparent electrode, DNTPD was vacuum vacuum-deposited to a thickness of 600 Pa to form a hole injection layer. On the hole injection layer, 50 B of BPBPA and 600 PC of PCZAC were sequentially vacuum-deposited to form a hole transport layer. Subsequently, compound 1 and 4CzIPN were vacuum-deposited in a weight ratio of 20:1 on the hole transport layer at a thickness of 200 mm 2 to form a light emitting layer.

DBFTrz and ZADN were sequentially formed on the light emitting layer to form an electron transport layer with a thickness of 350 Pa. On the electron transport layer, lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1,000 순차적 were sequentially deposited to form an electron injection layer and a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 Å/sec, and the aluminum was maintained at a deposition rate of 2 Å/sec, and the vacuum degree during deposition was 1 Х 10 ^An organic light emitting device was manufactured by maintaining ^-7 to 5 Х 10 ^-8 torr.

[DNTPD]: N,N′-diphenyl-N,N′'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′'-diamine

[BPBPA]: N-(4-Bromophenyl)-[1,1'-biphenyl]-4-amine

[PCZAC]: 9,9-dimethyl-10-(9-phenyl-9H-carbazol-3-yl)-9,10-dihydroacridine)

[DBFTrz]: 2,8-bis(4,6-diphenyl-1,3,5-triazin-2-yl)dibenzo[b,d]furan

[ZADN]: 2-[4-(9,10-Di-naphthalen-2-yl-anthracen-2-yl)-phenyl]-1-phenyl-1H-benzoimidazole

[4CzIPN]

Example 1-2: Preparation of an organic light emitting device to which the compound 2 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 2 instead of the compound 1 in Example 1-1.

Example 1-3: Fabrication of organic light emitting device to which compound 3 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 3 instead of the compound 1 in Example 1-1.

Example 1-4: Preparation of an organic light emitting device to which the compound 4 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 4 instead of the compound 1 in Example 1-1.

Example 1-5: Preparation of an organic light emitting device to which the compound 5 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 5 instead of the compound 1 in Example 1-1.

Example 1-6: Preparation of an organic light emitting device applying the compound 6

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 6 instead of the compound 1 in Example 1-1.

Example 1-7: Preparation of an organic light emitting device applying the compound 7

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 7 instead of the compound 1 in Example 1-1.

Example 1-8: Preparation of an organic light emitting device to which the compound 8 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 8 instead of the compound 1 in Example 1-1.

Example 1-9: Preparation of an organic light emitting device to which the compound 9 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 9 instead of the compound 1 in Example 1-1.

Example 1-10: Preparation of an organic light emitting device to which the compound 10 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 10 instead of the compound 1 in Example 1-1.

Example 1-11: Preparation of an organic light emitting device applying the compound 11

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 11 instead of the compound 1 in Example 1-1.

Example 1-12: Preparation of an organic light emitting device applying the compound 12

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound 12 instead of the compound 1 in Example 1-1.

[Comparative Example 1]

Comparative Example 1: Preparation of an organic light emitting device to which Comparative Compound 1 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using GH 1 (CBP) instead of the compound 1.

[GH 1(CBP)]

[Comparative Example 2]

Comparative Example 2: Preparation of an organic light emitting device to which Comparative Compound 2 is applied

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using GH 2 (DCz) instead of the compound 1.

[GH 2(DCz)]

Current-voltage-luminance (IVL) and color coordinates of the organic light-emitting devices manufactured by Examples 1-1 to 1-12 and Comparative Examples 1 and 2 using a PR-655 IVL meter manufactured by Photo Research (CIE), quantum efficiency (QE), luminous efficiency (LE), and current efficiency (J) characteristics were measured, and the results are shown in Tables 1 and 2 below.

compound
(Host) Voltage (V)
(@10mA/cm ² ) Efficiency (cd/A)
(@10mA/cm ² ) Color coordinate (x, y)
(CIE) Example 1-1 Compound 1 4.8 33.7 0.34, 0.61 Example 1-2 Compound 2 4.7 34.1 0.33, 0.65 Example 1-3 Compound 3 4.3 35.5 0.31, 0.60 Example 1-4 Compound 4 4.5 32.9 0.35, 0.61 Example 1-5 Compound 5 4.8 34.8 0.33, 0.62 Example 1-6 Compound 6 4.7 35.0 0.33, 0.60 Example 1-7 Compound 7 4.5 35.4 0.34, 0.64 Example 1-8 Compound 8 4.9 33.8 0.34, 0.65 Example 1-9 Compound 9 4.7 35.1 0.32, 0.65 Example 1-10 Compound 10 4.4 36.0 0.35, 0.63 Example 1-11 Compound 11 4.5 35.9 0.34, 0.58 Example 1-12 Compound 12 4.5 34.5 0.33, 0.59 Comparative Example 1 GH 1 (CBP) 6.1 28.7 0.33, 0.57 Comparative Example 2 GH 2 (DCz) 6.4 27.1 0.32, 0.58

Quantum efficiency (%) Luminous efficiency (lm/W) Current efficiency (Cd/A) 1000cd max. 1000cd max. 1000cd max. Example 1-1 19.2 23.7 23.4 28.1 44.4 48.8 Example 1-2 19.6 24.8 25 32.5 49.1 53.3 Example 1-3 20.5 26.9 26.5 33.9 51.9 55.4 Example 1-4 18.9 24.3 28.3 35 51.7 53 Example 1-5 19.7 23.5 24.8 27.4 45 48.7 Example 1-6 20.1 26.3 25.7 30.8 48.7 50.4 Example 1-7 20.2 26.6 25.1 31.6 47.8 51.8 Example 1-8 19.6 25.6 26.4 30.4 48.5 53.6 Example 1-9 20.0 24.7 25.1 31.7 46.1 50.9 Example 1-10 19.9 26.0 24.9 29.8 50.4 53.1 Example 1-11 18.7 25.5 24.4 30.0 48.6 51.8 Example 1-12 19.0 25.4 26.3 28.7 46.3 54.1 Comparative Example 1 15.7 19.1 21.2 23.3 40.1 43.7 Comparative Example 2 14.9 19.3 20.5 24.7 41.9 44.0

As can be seen from the results of Examples 1-1 to 1-12 and Comparative Examples 1 and 2 of Tables 1 and 2, the compound represented by Formula 1 was used as a host for the delayed fluorescent emission layer, and any of Formulas 2 to 5 was used. It can be seen that the organic light emitting device including the second compound represented by one as a dopant has improved luminous efficiency while lowering the driving voltage. Specifically, the compound represented by Formula 1 of the present invention is dibenzofuran, dibenzothiophene , Arylene linkage or combination of carbazole has a polarity (bipolar), and by introducing a substituent such as cyano group (-CN) has a mild n-type characteristics, holes and electrons in the light emitting layer It is easy to adjust the balance of (electron). On the other hand, in the case of the compound containing the carbazole and triazine groups of Comparative Example 2, the n-type properties were too enhanced, making it difficult to control the balance of holes and electrons in the light emitting layer.

Claims (14)

A first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,
The organic layer includes a light emitting layer,
The light emitting layer includes a first compound and a second compound,
The first compound is represented by any one of the following compounds,
The second compound is an organic light emitting device represented by the following formula 2 or formula 3:

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,
X ₂ to X ₄ are the same or different, each independently N or CR'R'',
R5 to R9, R7', R'and R'' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; Or NRaRb, or may combine with an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heteroring,
Ra and Rb together with the nitrogen atom to which they are attached may form a substituted or unsubstituted heterocyclic group,
m2 and n2 are each independently an integer from 0 to 4,
u1 is an integer from 1 to 5,
u2 is an integer from 0 to 5,
u3 is an integer from 0 to 5,
u3' is an integer from 0 to 4,
u1+u2+u3≤6,
u1+u2+u3'≤5,
When m2 is 2 or more, R5 is the same as or different from each other,
When n2 is 2 or more, R6 is the same as or different from each other,
When u3 is 2 or more, R7 is the same as or different from each other,
When u3' is 2 or more, R7' is the same as or different from each other. delete delete delete delete The method according to claim 1, wherein the NRaRb is an organic light emitting device represented by any one of the following formulas 6 to 12:
[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Chemical Formulas 6 to 12,
R25 to R31 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituted or unsubstituted alkyl group,
R27 and R28 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring,
q and r are each independently an integer from 0 to 4,
s is an integer from 0 to 2,
When q is 2 or more, R25 is the same as or different from each other,
When r is 2 or more, R26 is the same or different from each other,
When s is 2, R29 is the same or different from each other. The method according to claim 1, The second compound of the lowest triplet state (T1) and the singlet excited state (S1) of the energy level difference (ΔEst) of less than 0.3 eV organic light emitting device. delete A first electrode; A second electrode; And an organic material layer provided between the first electrode and the second electrode,
The organic layer includes a light emitting layer,
The light emitting layer includes a first compound and a second compound,
The first compound is represented by any one of the following compounds,

The second compound is an organic light emitting device that is represented by any one of the following compounds:

. The method according to claim 1 or claim 9, The light emitting layer is an organic light emitting device that further comprises a phosphorescent dopant. The organic light emitting device of claim 10, wherein the phosphorescent dopant is an iridium complex. The method according to claim 10, The content of the second compound is greater than the content of the phosphorescent dopant organic light emitting device. The organic light emitting diode of claim 1 or 9, wherein the second compound is contained in an amount of 0.01 to 50 parts by weight based on 100 parts by weight of the first compound. The method according to claim 1 or claim 9, The organic layer is an organic light emitting device further comprises at least one selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a hole blocking layer.

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