KR102379743B1 - Organic light emitting device - Google Patents

Abstract

anode; cathode; and an organic layer interposed between the anode and the cathode, wherein the organic layer includes a mixed organic layer,
the mixed organic layer contains two or more compounds; A device in which the triplet energy of at least one of the two or more compounds is 2.2 eV or more is disclosed.

Description

Organic light emitting device

It relates to an organic light emitting device.

An organic light emitting device is a self-luminous device, and has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and multicolorization.

In the organic light emitting device, a first electrode is disposed on a substrate, and a hole transport region, a light emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. can have a structure with Holes injected from the first electrode move to the emission layer via the hole transport region, and electrons injected from the second electrode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer region to generate excitons. Light is generated as this exciton changes from an excited state to a ground state.

It is to provide a novel organic light emitting device.

According to one aspect, the anode; cathode; and an organic layer interposed between the anode and the cathode.

The organic layer is i) interposed between the anode and the light emitting layer, and a hole transport region including at least one of a hole injection layer, a hole transport layer, a buffer layer and an electron blocking layer, and ii) is interposed between the light emitting layer and the cathode, a hole blocking layer , an electron transport region comprising at least one of an electron transport layer and an electron injection layer;

a mixed organic layer is interposed between the light emitting layer and the electron transport region;

the mixed organic layer contains two or more compounds;

There is provided an organic light-emitting device in which triplet energy of at least one compound among the two or more compounds is 2.2 eV or more.

The light emitting device according to the exemplary embodiment of the present invention may have a low driving voltage, high efficiency, high luminance, and a long lifespan.

1 is a diagram schematically illustrating a structure of an organic light emitting device according to an exemplary embodiment.

In one aspect of the present invention, an organic light emitting device includes an anode; cathode; and an organic layer interposed between the anode and the cathode.

The organic layer is i) interposed between the anode and the light emitting layer, and a hole transport region including at least one of a hole injection layer, a hole transport layer, a buffer layer and an electron blocking layer, and ii) is interposed between the light emitting layer and the cathode, a hole blocking layer , an electron transport region comprising at least one of an electron transport layer and an electron injection layer;

a mixed organic layer is interposed between the light emitting layer and the electron transport region;

the mixed organic layer contains two or more compounds;

At least one of the two or more compounds has a triplet energy of 2.2 eV or more.

According to the prior art, by introducing an additional layer between the light emitting layer and the electron transport layer, device performance such as an increase in driving voltage due to the accumulation of holes may occur. In addition, recombination of holes and electrons may occur intensively on the cathode side of the light emitting layer where electron carriers are accumulated, leading to a decrease in light emission lifetime.

A compound composed of an EWG having electron transport ability and a hydrocarbon-based ring is generally used for the cathode side based on the light emitting layer, but the device of the present invention includes a mixed organic layer containing two or more kinds of compounds, and among the two or more kinds of compounds A compound in which the triplet energy of at least one compound is 2.2 eV or higher is introduced.

The triplet energy of the one kind of compound may be 2.2 eV or more, and may be, for example, 2.2 eV to 4.0 eV, for example, 2.2 eV to 3.8 eV. When the triplet energy is within the above range, the light emitting device according to an embodiment of the present invention has a low driving voltage, high efficiency, high luminance, and a long lifespan.

According to one embodiment of the present invention, the light emitting layer may be a phosphorescent light emitting layer.

According to one embodiment of the present invention, the light emitting layer may be a fluorescent light emitting layer.

According to an embodiment of the present invention, the mixed organic layer may be in contact with the light emitting layer, and the triplet energy of at least one compound of the mixed organic layer may be greater than the triplet energy value of the dopant of the light emitting layer.

According to one embodiment of the present invention, the at least one compound may be an electron transport material or a hole transport material.

According to one embodiment of the present invention, the two or more kinds of compounds include a hole transporting compound and an electron transporting compound, and the hole transporting compound may be present in a weight ratio of 0.1 to 10 based on 1 by weight of the electron transporting compound. . When the weight ratio is within the above range, the light emitting device according to an embodiment of the present invention has a low driving voltage, high efficiency, high luminance, and a long lifespan.

According to one embodiment of the present invention, the two or more kinds of compounds include a hole transporting compound and an electron transporting compound, and the electron affinity (EA1) of the hole transporting compound and the electron affinity (EA2) of the electron transporting compound are The following relationship can be satisfied:

EA1 < EA2

The electron affinity EA1 of the hole-transporting material and the electron affinity EA2 of the electron-transporting material satisfy the relationship EA1 < EA2. The electrons injected from the cathode go through the electron transport layer and go through the electron-transporting material with a relatively high electron affinity as main. It migrates, and the additionally introduced hole transporting material serves to block some of the moving electrons.

In the device structure of the present invention, electron leakage occurs because electrons function as main carriers. By introducing a hole transporting material that blocks electrons between the light emitting layer/electron transport layer, some electrons are blocked in the mixed organic layer and Contributes to balancing the charge.

According to one embodiment of the present invention, the two or more kinds of compounds may include different electron transporting compounds.

According to one embodiment of the present invention, the light emitting layer is a phosphorescent light emitting layer, and may include an Ir, Pt, Cu or Os complex as a dopant.

According to one embodiment of the present invention, the thickness of the mixed organic layer may be 5 Å to 400 Å. For example, the thickness of the mixed organic layer may be 10 Å to 40 Å.

The triplet blocking function of the mixed organic layer according to an embodiment of the present invention is mainly determined by the skeletal structure of the mixed organic layer material. In general, when triplet excitons generated in the light emitting layer transfer their energy to an adjacent mixed organic layer, the triplet energy is transferred to the structure having the lowest triplet energy in each skeletal region of the mixed organic layer constituting material. . Therefore, in order to effectively confine the formed excitons in the light emitting layer, the triplet energy of the mixed organic layer material should be high, preferably 2.2 eV or more.

Specific skeletal structures having triplet energy of 2.2 eV or more include Benzene (3.66 eV), Phenathrene (2.70 eV), Naphthalene (2.63 eV), Chrysene (2.48 eV), Fluorene (2.94 eV), Triphenylene (2.90 eV), Fluoranthene ( 2.30 eV), Carbazole (3.18 eV), Dibenzofuran (2.97 eV), Dibenzothiophen (2.99 eV), Phenanthrorine (2.75 eV), Benzoimidazole (3.31 eV), and the like.

Therefore, it is preferable that the mixed organic layer material in the present invention consists of a skeleton having a high triplet energy or a compound in which the skeletons are substituted. A specific high T1 skeleton structure may be any one of the following formulas, but is not limited thereto.

According to an embodiment of the present invention, the mixed organic layer may include two or more of the following compounds:

According to an embodiment of the present invention, the emission layer may include dopants BD, Ir(ppy)3, or Ir(pq)2acac, but is not limited thereto.

According to one embodiment of the present invention, the light emitting layer may include one or more of the following compounds as a host, but is not limited thereto:

Hereinafter, the definition of a representative substituent among the substituents used in the present specification is as follows (the number of carbon atoms limiting the substituent is non-limiting and does not limit the characteristics of the substituent, and the definition of a substituent not defined in this specification is general by definition).

In the present specification, the C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, and the like. In the present specification, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula of -OA ₁₀₁ (here, A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group , an isopropyloxy group, and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group including one or more carbon double bonds in the middle or at the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group. etc. are included. In the present specification, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

In the present specification, the C ₂ -C ₆₀ alkynyl group refers to a hydrocarbon group including one or more carbon triple bonds in the middle or at the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group, a propynyl group (propynyl), and the like. In the present specification, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclo a heptyl group; and the like. In the present specification, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

In the present specification, the C ₂ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, and its Specific examples include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In the present specification, the C ₂ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one double bond in the ring, but not having aromaticity, and a specific Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, the C ₂ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, and at least in the ring has one double bond. Specific examples of the C ₂ -C ₁₀ heterocycloalkenyl group include a 2,3-hydrofuranyl group, a 2,3-hydrothiophenyl group, and the like. In the present specification, the C ₂ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkenyl group.

In the present specification, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group is a carbo group having 6 to 60 carbon atoms. It refers to a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be fused to each other.

In the present specification, the C ₂ -C ₆₀ heteroaryl group refers to a monovalent group including at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 2 to 60 carbon atoms. and C ₂ -C ₆₀ heteroarylene group means a divalent group including at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 2 to 60 carbon atoms do. Specific examples of the C ₂ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C ₂ -C ₆₀ heteroaryl group and the C ₂ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other.

In the present specification, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (here, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group is -SA ₁₀₃ (here , A ₁₀₃ is the above C ₆ -C ₆₀ aryl group).

In the present specification, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring-forming atom, and the entire molecule is non-aromatic. means a monovalent group having (eg, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, the monovalent non-aromatic condensed heteropolycyclic group includes two or more rings condensed with each other, and a hetero atom selected from N, O, P and S in addition to carbon as a ring forming atom, and , refers to a monovalent group (eg, having 2 to 60 carbon atoms) in which the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. In the present specification, the condensed divalent non-aromatic heteropolycyclic group refers to a divalent group having the same structure as the condensed monovalent non-aromatic heteropolycyclic group.

In the present specification, the substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocycloal Kenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₂ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group , a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed polycyclic group at least one substituent Is,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, - C ₁ -C ₆₀ alkyl group, C ₂ substituted with at least one of N(Q ₁₁ )(Q ₁₂ ), —Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), and —B(Q ₁₆ )(Q ₁₇ ) -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke group, substituted with at least one of -B(Q 26 )(Q 27 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non- aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group , a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, the above substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocyclo Alkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₂ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ arylox At least one of a group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed polycyclic group The substituent is

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaph Tyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazole Diary, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group , purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridi Nyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadia Zolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -N (Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alke a nyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, flu Orenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group , naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyra Zolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group , quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenane Trollinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, Cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di benzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, pr Thalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Zolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) ) and -B(Q ₂₆ )(Q ₂₇ ) substituted with at least one of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group , azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro -fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazole Diary, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, Isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di benzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

The Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azule Nyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoran Tenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group , pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group , carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazole Diary, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group , may be selected from an imidazopyrimidinyl group.

In the present specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, and "ter-Bu" or "But ^t " means a tert-butyl group.

In the present specification, "(organic layer) includes one or more condensed cyclic compounds" means "(organic layer) 1 type of condensed cyclic compound belonging to the scope of Formula 1 or two different types of fused cyclic compound belonging to the scope of Formula 1 above" may include more than one condensed cyclic compound".

In the present specification, the term “organic layer” refers to a single and/or a plurality of all layers interposed between the first electrode and the second electrode among the organic light emitting diodes. The material included in the layer of the "organic layer" is not limited to an organic material.

1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

Hereinafter, a structure and a manufacturing method of an organic light emitting device according to an exemplary embodiment of the present invention will be described with reference to FIG. 1 .

A substrate may be additionally disposed on a lower portion of the first electrode 110 or an upper portion of the second electrode 190 of FIG. 1 . As the substrate, a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, handling and waterproofness may be used.

The first electrode 110 may be formed, for example, by providing a material for the first electrode on the upper portion of the substrate using a deposition method or a sputtering method. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, may be used. Alternatively, in order to form the first electrode 110 that is a transflective electrode or a reflective electrode, as a material for the first electrode, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca) ), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) may be selected.

The first electrode 110 may have a single layer or a multilayer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

An organic layer 150 is disposed on the first electrode 110 . The organic layer 150 includes a light emitting layer.

The organic layer 150 includes a hole transport region interposed between the first electrode and the light emitting layer, an electron transport region interposed between the light emitting layer and the second electrode, and the light emitting layer; It may further include a mixed organic layer interposed between the electron transport regions.

The hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, and an electron blocking layer (EBL), and the electron transport region may include a hole blocking layer (HBL), an electron transport layer It may include at least one of (ETL) and an electron injection layer (EIL), but is not limited thereto.

The hole transport region may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region may have a single layer structure made of a plurality of different materials, or a hole injection layer/hole transport layer, a hole injection layer/hole transport layer/buffer layer that are sequentially stacked from the first electrode 110 . , a hole injection layer/buffer layer, a hole transport layer/buffer layer, or a hole injection layer/hole transport layer/electron blocking layer, but is not limited thereto.

When the hole transport region includes a hole injection layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, laser induced thermal imaging (LITI) The hole injection layer may be formed on the first electrode 110 by using various methods, such as.

When the hole injection layer is formed by vacuum deposition, deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., a vacuum degree of about 10 ^-8 to about 10 ^-3 torr, and about 0.01 to about 100 Å/sec. Within the deposition rate range of , the compound may be selected in consideration of a compound for a hole injection layer to be deposited and a structure of a hole injection layer to be formed.

When the hole injection layer is formed by the spin coating method, the coating conditions are within the range of a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80° C. to 200° C., the compound for the hole injection layer to be deposited and the hole to be formed. It may be selected in consideration of the injection layer structure.

When the hole transport region includes a hole transport layer, a vacuum deposition method, a spin coating method, a casting method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser thermal imaging (LITI) method, etc. The hole transport layer may be formed on the first electrode 110 or on the hole injection layer by using the same various methods. When the hole transport layer is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions of the hole transport layer refer to the deposition conditions and coating conditions of the hole injection layer.

The hole transport region is, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-NPB, TAPC, HMTPD, TCTA (4,4',4"- Tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine)), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: polyaniline/dodecylbenzenesulfonic acid), PEDOT/PSS ( Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonicacid:polyaniline/camphor) sulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), a compound represented by the following Chemical Formula 201 and a compound represented by the following Chemical Formula 202. can do:

<Formula 201>

<Formula 202>

In Formulas 201 and 202,

For descriptions of L ₂₀₁ to L ₂₀₅ , refer to the description of L ₁ in the present specification independently of each other;

xa1 to xa4 are each independently selected from 0, 1, 2 and 3;

xa5 is selected from 1, 2, 3, 4 and 5;

R ₂₀₁ to R ₂₀₄ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group , substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group is chosen

For example, in Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are each independently,

Phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorene group, dibenzofluorene group, phenanthrenylene group, anthracenylene group, pyrenylene group, chrysenylene group, pyridinyl a ren group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carba phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, Anthracenylene group, pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group , a carbazolylene group and a triazinylene group; is selected from;

xa1 to xa4 are each independently 0, 1 or 2;

xa5 is 1, 2 or 3;

R ₂₀₁ to R ₂₀₄ are each independently,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, azulenyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenane Trenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carba A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, substituted with at least one of a zolyl group and a triazinyl group , chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; may be selected from, but is not limited thereto.

The compound represented by Chemical Formula 201 may be represented by the following Chemical Formula 201A:

<Formula 201A>

For example, the compound represented by Formula 201 may be represented by Formula 201A-1 below, but is not limited thereto:

<Formula 201A-1>

The compound represented by Formula 202 may be represented by Formula 202A, but is not limited thereto:

<Formula 202A>

In Formulas 201A, 201A-1, and 202A, descriptions of L ₂₀₁ to L ₂₀₃ , xa1 to xa3 , xa5 and R ₂₀₂ to R ₂₀₄ in Formulas 201A, 201A-1 and 202A refer to those described herein, and R ₂₁₁ refers to the description of R ₂₀₃ , and , R ₂₁₃ to R ₂₁₆ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a car Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ - C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, It may be selected from a C ₆ -C ₆₀ aryl group thio group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 201A, 201A-1 and 202A,

L ₂₀₁ to L ₂₀₃ are each independently,

phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, pyrenylene group, chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria A phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, substituted with at least one selected from among the zinyl groups , pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, carbazolyl a ren group and a triazinylene group; is selected from;

xa1 to xa3 are each independently 0 or 1;

R ₂₀₃ , R ₂₁₁ and R ₂₁₂ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid carboxylic acid or a salt thereof, sulfonic acid or a salt thereof , phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthree Nyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, substituted with at least one selected from a diyl group and a triazinyl group , chrysenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group , a quinazolinyl group, a carbazolyl group and a triazinyl group; is selected from;

R ₂₁₃ and R ₂₁₄ are independently of each other,

C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, C ₁ -C ₂₀ alkyl group substituted with at least one selected from a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group and a C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

R ₂₁₅ and R ₂₁₆ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, C ₁ -C ₂₀ alkyl group substituted with at least one selected from a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group and a C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

xa5 is 1 or 2.

In Formulas 201A and 201A-1, R ₂₁₃ and R ₂₁₄ may be bonded to each other to form a saturated or unsaturated ring.

The compound represented by Formula 201 and the compound represented by Formula 202 may include the following compounds HT1 to HT20, but are not limited thereto.

The hole transport region may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If the hole transport region includes both a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å to about It may be 2000 Angstroms, for example about 100 Angstroms to about 1500 Angstroms. When the thickness of the hole transport region, the hole injection layer, and the hole transport layer satisfies the above-described ranges, a satisfactory level of hole transport characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include a charge-generating material to improve conductivity in addition to the above-described material. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane quinone derivatives such as phosphorus (F4-TCNQ) and the like; metal oxides such as tungsten oxide and molybdenum oxide; and the following compound HT-D1, but is not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transport region may further include at least one of a buffer layer and an electron blocking layer in addition to the hole injection layer and the hole transport layer as described above. The buffer layer may serve to increase light emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the light emitting layer. As a material included in the buffer layer, a material capable of being included in the hole transport region may be used. The electron blocking layer is a layer serving to prevent electron injection from the electron transport region.

The hole transport layer may be composed of a first hole transport layer and a second hole transport layer, may include the same material at the same time, may be composed of different materials.

A vacuum deposition method, a spin coating method, a casting method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, or a laser induced thermal imaging (LITI) method on the upper portion of the first electrode 110 or on the hole transport region ) to form the light emitting layer using various methods such as When the light emitting layer is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions of the light emitting layer refer to the deposition conditions and coating conditions of the hole injection layer.

When the organic light emitting device 10 is a full-color organic light emitting device, it may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each light emitting layer and each sub-pixel. Alternatively, the light emitting layer has a structure in which a red light emitting layer, a green light emitting layer, and a blue light emitting layer are stacked, or has a structure in which a red light emitting material, a green light emitting material, and a blue light emitting material are mixed without layer distinction, so that white light can be emitted.

The emission layer may include a host and a dopant.

The host may include at least one of the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP and TCP:

Alternatively, the host may include a compound represented by the following Chemical Formula 301.

<Formula 301>

Ar ₃₀₁ -[(L ₃₀₁ ) _xb1 -R ₃₀₁ ] _xb2

In Formula 301,

Ar ₃₀₁ is

Naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorine fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indeno anthracene;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl groupoxy group, C ₆ -C ₆₀ aryl group thio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocondensed polycyclic group, and -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ) (wherein Q ₃₀₁ to Q ₃₀₃ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group) substituted with at least one selected from naphthalene, heptalene, fluorene , spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphen and inde noanthracene; is selected from;

For the description of L ₃₀₁ , refer to the description of L ₂₀₁ in the present specification;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, C ₁ -C ₂₀ alkyl group substituted with at least one selected from a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group and a C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

xb1 is selected from 0, 1, 2 and 3;

xb2 is selected from 1, 2, 3 and 4.

For example, in Formula 301,

L ₃₀₁ is,

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra A phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group and a chrysenylene group; is selected from;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Substituted with at least one selected from a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group selected, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group and a chrysenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group substituted with at least one selected from a cenyl group, a pyrenyl group and a chrysenyl group group, pyrenyl group and chrysenyl group; may be selected from, but is not limited thereto.

For example, the host may include a compound represented by the following Chemical Formula 301A:

<Formula 301A>

For the description of the substituent in Formula 301A, refer to the description in the present specification.

The compound represented by Formula 301 may include at least one of the following compounds H1 to H42, but is not limited thereto:

Alternatively, the host may include at least one of the following compounds H43 to H49, but is not limited thereto:

The dopant may include at least one of a fluorescent dopant and a phosphorescent dopant.

The phosphorescent dopant may include an organometallic complex represented by the following Chemical Formula 401:

<Formula 401>

In Formula 401,

M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thorium (TM);

X ₄₀₁ to X ₄₀₄ are each independently nitrogen or carbon;

A ₄₀₁ and A ₄₀₂ rings independently of each other, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spiro-fluorene, substituted or unsubstituted indene , substituted or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted furan, substituted or unsubstituted imidazole, substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, substituted or unsubstituted isothiazole, substituted or unsubstituted oxazole, substituted or unsubstituted isoxazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted substituted or unsubstituted benzoimidazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted isobenzothiophene, substituted or unsubstituted benzo oxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran and selected from substituted or unsubstituted dibenzothiophenes;

said substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, substituted substituted thiazole, substituted isothiazole, substituted oxazole, substituted isoxazole, substituted pyridine, substituted pyrazine, substituted pyrimidine, substituted pyridazine, substituted quinoline, substituted isoquinoline, substituted benzo Quinoline, substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted iso At least one substituent of benzoxazole, substituted triazole, substituted oxadiazole, substituted triazine, substituted dibenzofuran and substituted dibenzothiophene is

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent ratio -Aromatic heterocondensed polycyclic group, -N (Q ₄₀₁ ) (Q ₄₀₂ ), -Si (Q ₄₀₃ ) (Q ₄₀₄ ) (Q ₄₀₅ ) and -B (Q ₄₀₆ ) (Q ₄₀₇ ), C substituted with at least one of ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₂ -C ₆₀ heteroaryl group, and a non-aromatic condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl groupoxy group, C ₆ -C ₆₀ aryl group thio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₄₁₁ )(Q ₄₁₂ ), -Si(Q ₄₁₃ )(Q ₄₁₄ )(Q ₄₁₅ ) and -B(Q ₄₁₆ )(Q ₄₁₇ ), C ₃ -C _{10 cycloalkyl group, C 2 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group , C 2} -C ₁₀ heterocycloalke, substituted with at least one of -B(Q 416 )(Q 417 ) Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non- aromatic heterocondensed polycyclic group; and

-N(Q ₄₂₁ )(Q ₄₂₂ ), -Si(Q ₄₂₃ )(Q ₄₂₄ )(Q ₄₂₅ ) and -B(Q ₄₂₆ )(Q ₄₂₇ ); is selected from;

L ₄₀₁ is an organic ligand;

xc1 is 1, 2 or 3;

xc2 is 0, 1, 2 or 3.

L ₄₀₁ may be any monovalent, divalent, or trivalent organic ligand. For example, L ₄₀₁ is a halogen ligand (eg Cl, F), a diketone ligand (eg acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (eg picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon It may be selected from a monoxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorus ligand (eg, phosphine, phosphite), but is not limited thereto.

When A ₄₀₁ in Formula 401 has two or more substituents, two or more substituents of A ₄₀₁ may be bonded to each other to form a saturated or unsaturated ring.

When A ₄₀₂ in Formula 401 has two or more substituents, two or more substituents of A ₄₀₂ may be bonded to each other to form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A₄₀₁ 및 A₄₀₂는 각각 이웃하는 다른 리간드의 A₄₀₁ 및 A₄₀₂와 각각 직접(directly) 또는 연결기(예를 들면, C₁-C₅알킬렌기, -N(R')-(여기서, R'은 C₁-C₁₀알킬기 또는 C₆-C₂₀아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands in Formula 401

may be the same as or different from each other. In Formula ₄₀₁ , when xc1 is 2 or more, A ₄₀₁ and A _{402 are} each directly or a linking group (eg, C ₁ -C ₅ alkylene group, -N (R′)- (wherein R′ is a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₂₀ aryl group) or —C(=O)-) may be interposed therebetween.

The phosphorescent dopant may include at least one of the following compounds PD1 to PD74, but is not limited thereto:

Alternatively, the phosphorescent dopant may include the following PtOEP:

The fluorescent dopant may include at least one of the following DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6 and C545T.

Alternatively, the fluorescent dopant may include a compound represented by the following Chemical Formula 501:

<Formula 501>

In Formula 501,

Ar ₅₀₁ silver

*naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, Fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indo noanthracene;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group and -Si(Q ₅₀₁ )(Q ₅₀₂ )(Q ₅₀₃ ) (wherein Q ₅₀₁ to Q ₅₀₃ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group) substituted with at least one selected from naphthalene, heptalene, fluorene , spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphen and inde noanthracene; is selected from;

For the description of L ₅₀₁ to L ₅₀₃ , refer to the description of L ₂₀₁ in the present specification, respectively;

R ₅₀₁ and R ₅₀₂ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group, triazinyl group, dibenzofuranyl group and dibenzothio groupphenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, tria A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, substituted with at least one selected from a zinyl group, a dibenzofuranyl group, and a dibenzothio group phenyl group , anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , a triazinyl group and a dibenzofuranyl group and a dibenzothio group phenyl group; is selected from;

xd1 to xd3 are each independently selected from 0, 1, 2 and 3;

xb4 is selected from 1, 2, 3 and 4.

The fluorescent host may include at least one of the following compounds FD1 to FD8:

The content of the dopant in the light emitting layer may be generally selected from about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

The light emitting layer may have a thickness of about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light emitting layer satisfies the above range, excellent light emitting characteristics may be exhibited without a substantial increase in driving voltage.

The above-described mixed organic layer may be disposed on the emission layer.

The mixed organic layer is formed by various methods such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI). It may be formed on the light emitting layer. When the light emitting layer is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions of the mixed organic layer refer to the deposition conditions and coating conditions of the hole injection layer.

The compound constituting the mixed organic layer is the same as described above.

The mixed organic layer may have a thickness of about 5 Å to about 400 Å, or about 10 Å to about 40 Å. When the thickness of the mixed organic layer satisfies the above range, satisfactory device characteristics can be obtained without a substantial increase in driving voltage.

The hole-transporting compound of the mixed organic layer may be present in a weight ratio of 0.1 to 10 based on 1 by weight of the electron-transporting compound, but is not limited thereto.

Next, an electron transport region may be disposed on the mixed organic layer.

The electron transport region may include at least one of a hole blocking layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

For example, the electron transport region may have a structure of an electron transport layer/electron injection layer or a hole blocking layer/electron transport layer/electron injection layer sequentially stacked from the emission layer, but is not limited thereto.

According to an embodiment, the organic layer 150 of the organic light emitting device includes an electron transport region interposed between the light emitting layer and the second electrode 190 . The electron transport region may include at least one of an electron transport layer and an electron injection layer.

The electron transport layer may include at least one of BCP, Bphen, and Alq ₃ , Balq, TAZ, and NTAZ.

Alternatively, the electron transport layer may include at least one compound selected from a compound represented by the following Chemical Formula 601 and a compound represented by the following Chemical Formula 602:

<Formula 601>

Ar ₆₀₁ -[(L ₆₀₁ ) _xe1 -E ₆₀₁ ] _xe2

In Formula 601,

Ar ₆₀₁ is

Naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indenoanthracene;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₂ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocondensed polycyclic group, and -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ) (wherein Q ₃₀₁ to Q ₃₀₃ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group) substituted with at least one selected from naphthalene, heptalene, fluorene , spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphen and inde noanthracene; is selected from;

For the description of L ₆₀₁ , refer to the description of L ₂₀₁ in the present specification;

E ₆₀₁ silver,

pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group , isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, Carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group , azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group , fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, Ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, Sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, iso Benzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imida A pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Lidinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group , acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group , oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group; is selected from;

xe1 is selected from 0, 1, 2 and 3;

xe2 is selected from 1, 2, 3 and 4.

<Formula 602>

In Formula 602,

X ₆₁₁ is N or C-(L ₆₁₁ ) _xe611 -R ₆₁₁ , X ₆₁₂ is N or C-(L ₆₁₂ ) _xe612 -R ₆₁₂ , X ₆₁₃ is N or C-(L ₆₁₃ ) _xe613 -R ₆₁₃ and , at least one of X ₆₁₁ to X ₆₁₃ is N;

For a description of each of L ₆₁₁ to L ₆₁₆ , refer to the description of L ₂₀₁ in the present specification;

R ₆₁₁ to R ₆₁₆ are each independently,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria substituted with at least one of the zinyl groups, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group , pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

xe611 to xe616 are each independently selected from 0, 1, 2 and 3.

The compound represented by Formula 601 and the compound represented by 602 may be selected from the following compounds ET1 to ET15:

The electron transport layer may have a thickness of about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the above range, a satisfactory electron transport characteristic may be obtained without a substantial increase in driving voltage.

The electron transport layer may further include a metal-containing material in addition to the above-described material.

The metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

The electron transport region may include a hole blocking layer. The hole blocking layer may be formed in order to prevent the diffusion of triplet excitons or holes into the electron transport layer when the light emitting layer uses a phosphorescent dopant.

When the electron transport region includes a hole blocking layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, laser induced thermal imaging (LITI) The hole blocking layer may be formed on the light emitting layer by using various methods, such as. When the hole blocking layer is formed by vacuum deposition and spin coating, the deposition conditions and coating conditions of the hole blocking layer refer to the deposition conditions and coating conditions of the hole injection layer.

The hole blocking layer may include, for example, at least one of the following BCP and Bphen, but is not limited thereto.

The hole blocking layer may have a thickness of about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

The electron transport layer is, using various methods such as a vacuum deposition method, a spin coating method, a casting method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser thermal imaging method (Laser Induced Thermal Imaging, LITI), etc., It may be formed on the light emitting layer or on the hole blocking layer. When the electron transport layer is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions of the electron transport layer refer to the deposition conditions and coating conditions of the hole injection layer.

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190 .

The electron injection layer is formed by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI). , may be formed on the electron transport layer. When the electron injection layer is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions of the electron injection layer refer to the deposition conditions and coating conditions of the hole injection layer.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li ₂ O, BaO, and LiQ.

The electron injection layer may have a thickness of about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, a satisfactory level of electron injection characteristics may be obtained without a substantial increase in driving voltage.

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. In this case, the material for the second electrode 190 includes a metal, an alloy, an electrically conductive compound, and a mixture thereof having a low work function. can be used Specific examples of the material for the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In). , magnesium-silver (Mg-Ag), and the like may be included. Alternatively, ITO or IZO may be used as the material for the second electrode 190 . The second electrode 190 may be a reflective electrode, a transflective electrode, or a transmissive electrode.

On the other hand, the organic layer of the organic light emitting device according to an embodiment of the present invention may be formed by a deposition method using a compound according to an embodiment of the present invention, or a compound according to an embodiment of the present invention prepared as a solution It can also be formed by a wet method of coating the

The organic light emitting diode according to the exemplary embodiment of the present invention may be provided in various types of flat panel display devices, for example, a passive matrix organic light emitting display device and an active matrix organic light emitting display device. In particular, when provided in an active matrix organic light emitting display device, the first electrode provided on the substrate side may be electrically connected to a source electrode or a drain electrode of the thin film transistor as a pixel electrode. In addition, the organic light emitting device may be provided in a flat panel display capable of displaying a screen on both sides.

In the above, the organic light emitting device has been described with reference to FIG. 1, but is not limited thereto.

Hereinafter, an organic light emitting diode according to an embodiment of the present invention will be described in more detail by way of example. (The compounds used in the following examples are all known compounds, and those skilled in the art can easily obtain them)

Example

blue device manufacturing

ITO/HTM (120)/Host+ BD　5%(30)/Buffer (20)/Alq3 (20)/LiF (1)/Al (200)

Example 1-1

A transparent electrode of indium tin oxide (ITO) having a thickness of 120 nm was formed on a glass substrate. Then, this was subjected to ultrasonic cleaning and pretreatment (UV-O ₃ treatment, heat treatment).

On the pretreated anode, the compound HTM was deposited to a thickness of 120 nm as a hole transport layer. Then, compound BD, which is a doping material, was co-deposited at 5% on MADN, which is a host material, to form a light emitting layer having a thickness of 30 nm. On this light emitting layer, as a buffer layer, compound BF1 and compound BF9 were vapor-deposited to a thickness of 20 nm in a ratio of 1:1, and then Alq was vapor-deposited to a thickness of 20 nm as an electron transport layer. Then, as a cathode, lithium fluoride was vapor-deposited to a thickness of 1 nm, followed by deposition of aluminum to a thickness of 200 nm to fabricate an organic light-emitting device.

Table 1 shows the comparison results by measuring the physical properties of the buffer layer material. The method of measuring the physical property value is as follows.

(1) Ionization potential (IP)

The organic material was irradiated with light, and the amount of electrons generated by charge separation at that time was measured.

(2) Energy Gap (Eg)

It was calculated from the edge of the UV absorption spectrum of the material.

(3) Electron affinity (EA)

The measured values of the ionization potential (IP) and the energy gap (Eg) were calculated by substituting them into the following equations.

EA(eV) = IP - Eg

(4) triplet energy (ET)

The conversion formula for triplet energy (ET) is as follows.

ET(eV) = 1239.85 / λedge

λedg denotes a wavelength value at the intersection of the tangent and the horizontal axis by drawing a tangent to the slope of the short wavelength side of the phosphorescence spectrum.

substance name EA (eV) IP (eV) Eg (eV) ET (eV) BF1 3 6.1 3.1 2.67 BF2 2.21 5.84 3.63 2.64 BF3 2.1 5.5 3.4 2.9 BF4 2.35 5.67 3.32 2.87 BF5 2.4 5.9 3.5 3 BF6 2 5.5 3.5 2.9 BF7 2.8 5.9 3.1 1.8 BF8 2.5 5.7 3.2 2.6 BF9 2.77 5.49 2.72 2.67 BF10 2.9 6.4 3.5 2.5 BF11 2.7 6.3 3.6 2.7 BF12 3 6.12 3.12 2.27

Examples 1-2 to 1-14, Comparative Examples 1-3

ITO/HTM (120)/Host+ BD　5%(30)/Buffer (20)/Alq3 (20)/LiF (1)/Al (200)

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the buffer layer on the light emitting layer was changed to the compound shown in Table 2.

EML Buffer efficiency
(cd/A) drive voltage
(V) T90
(hr) Example 1-1 MADN + BD BF1+BF9 5.5 4.5 98 Example 1-2 MADN + BD BF2+BF9 5.9 4.5 110 Example 1-3 MADN + BD BF3+BF9 5.7 4.6 85 Example 1-4 MADN + BD BF4+BF9 5.8 4.5 106 Example 1-5 MADN + BD BF5+BF9 5.5 4.6 94 Example 1-6 MADN + BD BF6+BF9 5.6 4.5 86 Example 1-7 MADN + BD BF4+BF7 5.6 4.3 81 Examples 1-8 MADN + BD BF5+BF8 5.8 4.4 103 Examples 1-9 MADN + BD BF6+BF8 5.5 4.4 98 Examples 1-10 MADN + BD BF4+BF10 5.7 4.4 92 Example 1-11 MADN + BD BF4+BF11 5.4 4.3 78 Example 1-12 MADN + BD BF4+BF12 5.6 4.6 96 Examples 1-13 MADN + BD BF7+BF9 5.4 4.2 82 Example 1-14 MADN + BD BF8+BF9 5.6 4.3 98 Comparative Example 1 MADN + BD Alq3 4.5 4.8 35 Comparative Example 2 MADN + BD BF7 4.8 4.7 48 Comparative Example 3 MADN + BD BF4 4.8 5.0 29

Efficiency (cd/A), voltage (V), and lifetime (time) were respectively evaluated for the devices of Examples and Comparative Examples, and the results are shown in Table 2 above.

Green device manufacturing

ITO/HTM (120)/Host+ Ir(ppy)3_10%　(30)/Buffer (20)/Alq3 (20)/LiF (1)/Al (200)

Examples 2-1 to 6, Comparative Examples 4 to 6

Organic light emission in the same manner as in Example 1-1, except that the light emitting layer host, dopant, and buffer layers were changed to the compound shown in Table 3, and the dopant material, Ir(ppy)3, was deposited at a ratio of 10%. A device was fabricated (if there are two hosts, the weight ratio is 1:1).

EML Buffer efficiency
(cd/A) drive voltage
(V) T90
(hr) Example 2-1 CBP + Ir(ppy)3 BF4+BF7 55 4.8 165 Example 2-2 CBP + Ir(ppy)3 BF5+BF8 57 5.0 138 Example 2-3 CBP + Ir(ppy)3 BF6+BF8 55 4.8 151 Example 3-1 PH1 + Ir(ppy)3 BF4+BF7 57 5.2 181 Example 3-2 PH1 + Ir(ppy)3 BF5+BF8 58 5.1 144 Example 3-3 PH1 + Ir(ppy)3 BF6+BF8 55 5.1 160 Example 4-1 PH2 + Ir(ppy)3 BF4+BF7 61 4.5 120 Example 4-2 PH2 + Ir(ppy)3 BF5+BF8 63 4.8 137 Example 4-3 PH2 + Ir(ppy)3 BF6+BF8 60 4.7 118 Example 5-1 CBP + PH1 + Ir(ppy)3 BF4+BF7 68 4.5 177 Example 5-2 CBP + PH1 + Ir(ppy)3 BF5+BF8 66 4.5 201 Example 5-3 CBP + PH1 + Ir(ppy)3 BF6+BF8 65 4.6 165 Example 6 BF5 +BF8 + Ir(ppy)3 BF5+BF8 63 4.3 173 Comparative Example 4 CBP + Ir(ppy)3 Alq3 44 5.7 49 Comparative Example 5 CBP + Ir(ppy)3 BF7 48 5.3 66 Comparative Example 6 CBP + Ir(ppy)3 BF4 52 6.1 87

Efficiency (cd/A), voltage (V), and lifetime (time) were respectively evaluated for the devices of Examples and Comparative Examples, and the results are shown in Table 3 above.

red device manufacturing

ITO/HTM (120)/Host+ Ir(pq)2acac_5%　(30)/Buffer (20)/Alq3 (20)/LiF (1)/Al (200)

Examples 7-1 to 9-3, Comparative Examples 7 to 9

Organic light emission in the same manner as in Example 1-1, except that the light emitting layer host, dopant and buffer layers were changed to the compound shown in Table 4, and the dopant material, Ir(pq)2acac, was deposited at a ratio of 5%. made a small

EML Buffer efficiency
(cd/A) drive voltage
(V) T90
(hr) Example 7-1 CBP + Ir(pq)2acac BF4+BF7 23.1 5.3 151 Example 7-2 CBP + Ir(pq)2acac BF5+BF8 22.5 5.4 163 Example 7-3 CBP + Ir(pq)2acac BF6+BF8 24.3 5.3 170 Example 8-1 PH1 + Ir(pq)2acac BF4+BF7 23.3 5.4 225 Example 8-2 PH1 + Ir(pq)2acac BF5+BF8 21.8 5.5 166 Example 8-3 PH1 + Ir(pq)2acac BF6+BF8 24.0 5.5 191 Example 9-1 PH2 + Ir(pq)2acac BF4+BF7 25.1 5.1 243 Example 9-2 PH2 + Ir(pq)2acac BF5+BF8 24.8 5.0 288 Example 9-3 PH2 + Ir(pq)2acac BF6+BF8 23.5 4.9 260 Comparative Example 7 CBP + Ir(pq)2acac Alq3 15.3 5.9 118 Comparative Example 8 CBP + Ir(pq)2acac BF7 19.8 5.3 95 Comparative Example 9 CBP + Ir(pq)2acac BF4 18.0 6.5 76

Efficiency (cd/A), voltage (V), and lifetime (time) were respectively evaluated for the devices of Examples and Comparative Examples, and the results are shown in Table 3 above.

Looking at the results of Tables 2 to 4, it can be seen that the device according to one embodiment of the present invention has superior efficiency and lifespan than the device of the comparative example.

Although the present invention has been described with reference to the above synthesis examples and examples, these are merely exemplary, and those of ordinary skill in the art to which the present invention pertains can make various modifications and equivalent other examples therefrom. will understand Therefore, the true technical protection scope of the present invention should be determined by the technical spirit of the appended claims.

10: organic light emitting device
110: first electrode
150: organic layer
190: second electrode

Claims (19)

anode;
cathode; and
An organic light emitting device having an organic layer including a light emitting layer interposed between the anode and the cathode,
the organic layer
i) a hole transport region interposed between the anode and the light emitting layer and including at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer;
ii) an electron transport layer interposed between the light emitting layer and the cathode; and at least one of a hole blocking layer and an electron injection layer;
any one of the following compounds 1-1 to 1-123; And a mixed organic layer comprising any one of compounds 2-1 to 2-84 is interposed between the light emitting layer and the electron transport region,
The mixed organic layer is an organic light emitting device in contact with the light emitting layer and the electron transport region;

delete delete delete delete delete delete The method of claim 1,
The light emitting layer is a phosphorescent light emitting layer, and an organic light emitting device comprising an Ir, Pt, Cu or Os complex as a dopant. delete The method of claim 1,
An organic light emitting device in which the light emitting layer includes a dopant BD:

The method of claim 1,
An organic light-emitting device in which the light-emitting layer includes a dopant Ir(ppy)3:

The method of claim 1,
An organic light-emitting device in which the light-emitting layer includes a dopant Ir(pq)2acac:

The method of claim 1,
An organic light emitting device in which the light emitting layer includes at least one of the following compounds as a host:

According to claim 1,
An organic light emitting device, wherein the hole transport region includes at least one of a compound represented by the following Chemical Formula 201A and a compound represented by the following Chemical Formula 202A:
<Formula 201A>

<Formula 202A>

In Formulas 201A and 202A,
L ₂₀₁ to L ₂₀₃ are each independently,
phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, pyrenylene group, chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria A phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, substituted with at least one selected from among the zinyl groups , pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, carbazolyl a ren group and a triazinylene group; is selected from;
xa1 to xa3 are each independently 0 or 1;
R ₂₀₂ to R ₂₀₄ , R ₂₁₁ and R ₂₁₂ are each independently,
Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolyl a nyl group, a carbazolyl group and a triazinyl group; is selected from;
R ₂₁₃ and R ₂₁₄ are independently of each other,
C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, C ₁ -C ₂₀ alkyl group substituted with at least one selected from a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group and a C ₁ -C ₂₀ alkoxy group;
Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;
R ₂₁₅ and R ₂₁₆ are independently of each other,
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, C ₁ -C ₂₀ alkyl group substituted with at least one selected from a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group and a C ₁ -C ₂₀ alkoxy group;
Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group and triazinyl group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;
xa5 is 1 or 2. 15. The method of claim 14,
An organic light emitting device wherein the compound represented by Formula 201A and the compound represented by Formula 202A are any one of the following compounds:

The method of claim 1,
The organic light emitting device in which the hole transport region includes a p-dopant. The method of claim 1,
The hole transport region includes a p-dopant, and the p-dopant is a quinone derivative, a metal oxide, or a cyano group-containing compound. The method of claim 1,
An organic light-emitting device in which the organic layer is formed through a wet process. A flat panel display comprising the organic light emitting device of claim 1, wherein a first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

Images