KR20240068612A - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent device containing the same. By including the organic electroluminescent compound according to the present application, it has long lifespan and/or high luminous efficiency characteristics compared to conventional organic electroluminescent devices. An organic electroluminescent device having a can be provided.

Description

Organic electroluminescent compound and organic electroluminescent device comprising the same

The present invention relates to organic electroluminescent compounds and organic electroluminescent devices containing the same.

An electroluminescent device (EL device) is a self-luminous display device that has the advantages of a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak developed the first organic electroluminescent device using low-molecular aromatic diamine and aluminum complexes as materials for forming a light-emitting layer [Reference: Appl. Phys. Lett. 51, 913, 1987].

An organic electroluminescent device is a device that converts electrical energy into light by applying electricity to an organic luminescent material, and usually has a structure that includes an anode (anode), a cathode (cathode), and an organic layer between them. The organic material layer of the organic electroluminescent device includes a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., as needed. can do. Materials used in the organic material layer include hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials (including host and dopant materials), electron buffer materials, hole blocking materials, and electron depending on their functions. It can be divided into transmission materials, electron injection materials, etc. In such an organic electroluminescent device, holes are injected from the anode and electrons from the cathode are injected into the light-emitting layer by applying voltage, and excitons with high energy are formed by recombination of the holes and electrons. This energy causes the light-emitting organic compound to be excited, and as the excited state of the light-emitting organic compound returns to the ground state, the energy is emitted as light and emits light.

The light-emitting material of an organic electroluminescent device is the most important factor in determining the light-emitting efficiency of the device. The light-emitting material must have high quantum efficiency and high mobility of electrons and holes, and the formed light-emitting material layer must be uniform and stable. These light-emitting materials are divided into blue, green, or red light-emitting materials depending on the color of the light, and there are also yellow or orange light-emitting materials. Additionally, light-emitting materials can be divided into host materials and dopant materials in terms of functionality. Recently, the development of organic electroluminescent devices with high efficiency and long lifespan has emerged as an urgent task. In particular, considering the level of EL characteristics required for medium to large-sized OLED panels, the development of materials that are significantly superior to existing light emitting materials is urgently needed. .

Meanwhile, Korean Patent Publication No. 2017-0096769 and Korean Patent Registration No. 1814875 disclose heterocyclic compounds and organic electroluminescent devices containing them, but development to improve the performance of OLED devices is still required.

Korean Patent Publication No. 2017-0096769 (published on August 25, 2017) Korean Patent No. 1814875 (published on December 27, 2017)

The purpose of the present application is to provide an organic electroluminescent compound that is effective in producing an organic electroluminescent device having long lifespan and/or high luminous efficiency characteristics.

The present inventors completed the present invention by discovering that an organic electroluminescent compound represented by the following formula (1) achieves the above-mentioned purpose.

[Formula 1]

In Formula 1,

X is O or S;

R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) may be heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or may be connected to each other to form a ring;

One or more of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ are fused with each other to form a ring of the formula (2) below,

[Formula 2]

Among R ₅ to R ₈ that do not form a ring are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;

R ₉ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, , provided that at least one of R ₉ to R ₁₂ is ego;

L is a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene;

ETU is substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted benzofuropyrazinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted benzofuropyrimidinyl. , or substituted or unsubstituted benzothiopyrimidinyl.

The organic electroluminescent compound according to the present disclosure can provide an organic electroluminescent device with long lifespan and/or high luminous efficiency characteristics.

1 is a representative chemical formula of an organic electroluminescent compound according to the present disclosure.

The present application is described in more detail below, but this is for illustrative purposes only and should not be construed to limit the scope of the present application.

As used herein, “organic electroluminescent compound” refers to a compound that can be used in an organic electroluminescent device and, if necessary, may be included in any layer constituting the organic electroluminescent device.

As used herein, “organic electroluminescent material” refers to a material that can be used in an organic electroluminescent device, may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. You can.

As used herein, “(C1-C30)alkyl” means straight or branched chain alkyl having 1 to 30 carbon atoms in the chain, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl. As used herein, “(C2-C30)alkenyl” means straight-chain or branched-chain alkenyl having 2 to 30 carbon atoms in the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 20 carbon atoms. There are 10. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbut-2-enyl. As used herein, “(C2-C30)alkynyl” means a straight-chain or branched-chain alkynyl having 2 to 30 carbon atoms in the chain, where the carbon atoms are preferably 2 to 20, more preferably 2 to 20 carbon atoms. There are 10. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methylpent-2-ynyl. As used herein, “(C3-C30)cycloalkyl” refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As used herein, "(3-7 membered) heterocycloalkyl" has a ring skeleton of 3 to 7 atoms, preferably 5 to 7 atoms, and is a group consisting of B, N, O, S, Si and P, preferably O. , S and N, and includes cycloalkyl containing one or more heteroatoms selected from the group consisting of, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. As used herein, “(C6-C30)aryl(lene)” refers to a single-ring or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring carbon atoms, and may be partially saturated. The number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzoflu. Orenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobi. These include fluorenyl and azulenyl groups. More specifically, examples of the aryl include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl , benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl , 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o- Terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p- Terphenyl-2-yl, m-quarterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p -Tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p- tert -butylphenyl, p -(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4" -tert -butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl -2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl -2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, etc.

As used herein, “(3-30 membered) heteroaryl (lene)” refers to an aryl group having 3 to 30 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si and P. it means. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein includes forms where one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and also includes those having a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, and tetrazinyl. , triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. single ring heteroaryl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, iso Quinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, There are fused ring heteroaryls such as phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi Nyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imy Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3- Pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2 -Isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3 -Benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl , 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2- Quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl -1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, Azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl , 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4 -acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3- thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3- Methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2- tert -butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -Butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert -butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl , 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, etc. . As used herein, “halogen” includes F, Cl, Br and I atoms.

In addition, “ortho (o-)”, “meta (m-)”, and “para (p-)” are prefixes that indicate the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other. For example, when the substituents are in the 1st and 2nd positions in a benzene substituent, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions. For example, in a benzene substituent, when the substituents are at the 1st and 3rd positions, it is called a meta position. Para indicates that two substituents are at the 1 and 4 positions. For example, in a benzene substituent, when the substituents are at the 1 and 4 positions, it is called the para position.

In addition, 'substitution' in the expression "substituted or unsubstituted" described herein means replacing a hydrogen atom in a certain functional group with another atom or another functional group (i.e., a substituent). As used herein, substituted alkyl, substituted aryl(len), substituted heteroaryl(len), substituted silyl, substituted amino, substituted pyrimidine, substituted triazinyl, substituted quinazolinyl, substituted quinoxali. Nyl, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted dibenzoquinazolinyl, substituted benzofuropyrazinyl, substituted benzothiopyrazinyl, substituted benzofuro The substituents of pyrimidinyl and substituted benzothiopyrimidinyl are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2) -C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7) Circle) heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (3-30 membered)heteroaryl substituted or unsubstituted with (C6-C30)aryl, (3-30 membered)hetero Substituted or unsubstituted with aryl (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1- C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di- (C1-C30)alkylamino, mono- or di-(C6-C30)aryl unsubstituted or substituted with (C1-C30)alkyl Amino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)aryl boronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30) It is at least one selected from the group consisting of alkyl(C6-C30)aryl. According to one aspect of the present application, the substituents are each independently (C1-C20)alkyl, (C6-C25)aryl, (C6-C25)aryl (5-25 membered) heteroaryl substituted or unsubstituted, and (C1) -C10)alkyl(C6-C25)aryl or more. According to another aspect of the present application, the substituents are (5-20 membered) heteroaryl, each independently substituted or unsubstituted with (C1-C10)alkyl, (C6-C25)aryl, (C6-C18)aryl, and ( It is one or more of C1-C5)alkyl(C6-C25)aryl. For example, the substituents are each independently methyl, phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, and phenyl. It may be one or more of substituted carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzonaphthothiophenyl, and benzonaphthofuranyl.

Herein, the ring formed by linking adjacent substituents is a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring formed by linking or fusion of two or more adjacent substituents. meaning, and preferably may be a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring. Additionally, the ring formed may contain one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. For example, the fused ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, or a substituted or unsubstituted ring. fluorene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted indole ring, substituted or unsubstituted indene ring, substituted or unsubstituted benzene ring or substituted or It may be in the form of an unsubstituted carbazole ring.

In the formulas herein, heteroaryl(lene) and heterocycloalkyl may each independently include one or more heteroatoms selected from B, N, O, S, Si, and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1 -C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)aryl. At least one selected from the group consisting of amino may be combined.

In Formula 1, R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted. It may be ringed (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or may be connected to each other to form a ring. According to one aspect of the present application, R ₁ to R ₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5-30 members) It may be heteroaryl, or one or more of R ₁ and R ₂ , R ₂ and R ₃ , and R ₃ and R ₄ may be connected to each other to form a ring. According to another aspect of the present application, R ₁ to R ₄ are each independently hydrogen, deuterium, unsubstituted (C6-C18)aryl, or (5-25 members) substituted or unsubstituted with (C6-C18)aryl. It may be heteroaryl. For example, R ₁ to R ₄ may each independently be hydrogen, phenyl, naphthyl, biphenyl, phenanthrenyl, phenyl-substituted carbazolyl, dibenzothiophenyl, or dibenzofuranyl.

In Formula 1, one or more of R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ are fused with each other in Formula 2 below to form a ring. According to one aspect of the present application, R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ may be fused with each other in Formula 2 below to form a ring.

[Formula 2]

In Formula 1, those of R ₅ to R ₈ that do not fuse with Formula 2 to form a ring are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted. (C6-C30)aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to one aspect of the present application, R ₅ to R ₈ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C10)alkyl, substituted or unsubstituted (C6-C18)aryl, or substituted or unsubstituted It may be (5-20 won) heteroaryl. According to another aspect of the present application, R ₅ to R ₈ may each independently be hydrogen, deuterium, or unsubstituted (C6-C18)aryl. For example, R ₅ to R ₈ may each independently be hydrogen, phenyl, naphthyl, or biphenyl.

In Formula 1, R ₉ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted. It is substituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, am. At least one of R ₉ to R ₁₂ And, according to one aspect of the present application, any one of R ₉ to R ₁₂ is It can be. According to another aspect of the present application, R ₉ to R ₁₂ are each independently hydrogen, deuterium, or , provided that any one of R ₉ to R ₁₂ is It can be.

The L is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to one aspect of the present application, L is a single bond, substituted or unsubstituted (C6-C25)arylene, or substituted or unsubstituted (5-25 membered) heteroarylene. According to another aspect of the present application, L is a single bond, unsubstituted (C6-C18)arylene, or unsubstituted (5-20 membered) heteroarylene. For example, L can be a single bond, phenylene, naphthylene, biphenylene, or pyridylene.

The ETU is substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, Substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted benzopuropyrazinyl, substituted or unsubstituted benzothiopyrazinyl, substituted or unsubstituted benzofuropyrimi It is dinyl, or substituted or unsubstituted benzothiopyrimidinyl. According to one aspect of the present application, ETU is substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted benzofuropyrimidinyl, or substituted benzothiopyrimidinyl. The substituted triazinyl, substituted quinazolinyl, substituted quinoxalinyl, substituted benzoquinoxalinyl, substituted dibenzoquinoxalinyl, substituted benzoquinazolinyl, substituted benzofuropyrimidinyl, and substituted The substituents of the benzothiopyrimidinyl may each independently be one or more of substituted or unsubstituted (C6-C25)aryl and substituted or unsubstituted (5-30 membered)heteroaryl, and are preferably each independently phenyl. , naphthyl, biphenyl, phenanthrenyl, terphenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl substituted with phenyl, dibenzothiophenyl, dibenzofuran It may be one or more of 1, benzonaphthothiophenyl, and benzonaphthofuranyl. For example, ETU can be expressed in any of the following formulas.

In the above formula, R is each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30) (original) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted silyl, or substituted or unsubstituted amino. According to one aspect of the present application, R is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C10)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5-30) 1) It is heteroaryl. According to another aspect of the present application, R is each independently hydrogen, deuterium, (C6-C25)aryl substituted or unsubstituted with one or more of (C1-C10)alkyl and (C6-C18)aryl, or (C6- C18) It is a (5-30 membered) heteroaryl substituted or unsubstituted with aryl. For example, R is each independently substituted with hydrogen, phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, or phenyl. It may be carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzonaphthothiophenyl, or benzonaphthofuranyl.

The compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3.

[Formula 1-1] [Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, R ₅ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30) )aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino; R ₁ to R ₄ , L, ETU, and X are the same as defined in Formula 1. Additionally, in Formulas 1-1 to 1-3, preferred embodiments and specific examples of R ₁ to R ₁₂ , L, ETU, and X are as mentioned in Formula 1.

The compound represented by Formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto.

The organic electroluminescent compound of the present application can be prepared using synthetic methods known to those skilled in the art. For example, the organic electroluminescent compound of the present application can be synthesized as shown in Schemes 1 to 4 below, but is not limited thereto.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

In Schemes 1 to 4, R ₁ to R ₁₂ , X, L, and ETU are the same as defined in Formula 1, and Hal is halogen.

Although exemplary synthesis examples of the present invention represented by Formula 1 have been described above, they all include Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Specific synthesis examples based on intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN ₁ substitution reaction, SN ₂ substitution reaction, and Phosphine-mediated reductive cyclization reaction. Those skilled in the art will easily understand that the above reaction proceeds even if other substituents defined in Formula 1 are combined in addition to the substituents specified in .

Dopants that can be used in combination with the compounds herein can be one or more phosphorescent or fluorescent dopants, with phosphorescent dopants being preferred. The phosphorescent dopant is not particularly limited, but may be a complex of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, preferably iridium ( It may be an ortho-metalized complex compound of a metal atom selected from Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, more preferably, it may be an ortho-metalated iridium complex compound.

A compound represented by the following formula (101) may be used as a dopant included in the organic electroluminescent device of the present application, but is not limited thereto.

[Formula 101]

In Formula 101,

L is any one selected from structures 1 to 3 below;

[Structure 1] [Structure 2] [Structure 3]

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C6-C30)aryl, cyano, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₀ to R ₁₀₃ may have adjacent substituents connected to each other to form a substituted or unsubstituted fused ring with pyridine, for example, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzopuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted Noquinoline formation is possible;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, deuterium or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₄ to R ₁₀₇ may have adjacent substituents connected to each other to form a substituted or unsubstituted fused ring with benzene, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted It is possible to form a substituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothienopyridine;

R ₂₀₁ to R ₂₂₀ are each independently hydrogen, deuterium, halogen, deuterium or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, or substituted or unsubstituted (C6-C30)aryl, or adjacent substituents may be connected to each other to form a substituted or unsubstituted fused ring;

s is an integer from 1 to 3.

Specifically, specific examples of the dopant compound are as follows, but are not limited thereto.

The compound represented by Formula 1 herein may be included in one or more layers constituting the organic electroluminescent device, for example, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, It may be included in one or more layers selected from an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. Each of the above layers may be further composed of multiple layers.

In addition, the compound represented by Formula 1 herein is not limited thereto, but may be included in the light-emitting layer and/or the electron transfer zone. The compound represented by Formula 1 herein may be included as a host material in the light-emitting layer, and simultaneously or selectively, may be included as an electron buffer material and/or hole blocking material in the electron transfer band.

The electron transport zone of the present application may be composed of one or more layers selected from the group consisting of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and each of the layers may be composed of one or more layers. Preferably, the electron transfer zone includes an electron buffer layer and/or a hole blocking layer. Additionally, the electron transfer zone may further include one or more layers of an electron transfer layer and an electron injection layer.

Among the organic electroluminescent materials of the present disclosure, for example, hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. One or more materials may include a compound represented by Formula 1 above. The organic electroluminescent material may be one or more of a light emitting material, an electron buffer material, and a hole blocking material. The organic electroluminescent material may be composed solely of the compound represented by Formula 1, or may further include common materials included in organic electroluminescent materials. When two or more types of materials are included in one layer, they may be mixed and deposited to form a layer, or they may be co-deposited separately and simultaneously to form a layer.

The organic electroluminescent device of the present application includes a first electrode; second electrode; and one or more organic material layers interposed between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic material layer includes one or more light-emitting layers, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. It may further include one or more floors selected from the floors.

The first electrode and the second electrode may each be formed of a transparent conductive material, or may be formed of a transflective or reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-side emitting type. Additionally, the hole injection layer may be additionally doped with p-dopant, and the electron injection layer may be additionally doped with n-dopant.

The organic electroluminescent device of the present application may include the compound represented by Formula 1, and may further include common materials included in organic electroluminescent materials. An organic electroluminescent device containing the organic electroluminescent compound of the present application represented by Formula 1 may exhibit high luminous efficiency and/or long lifespan.

Additionally, the organic electroluminescent material according to an example of the present application can be used as a light emitting material for a white organic light emitting device. The white organic electroluminescent device is arranged in a side-by-side or stacking manner depending on the arrangement of the R (red), G (green), YG (yellow green), or B (blue) light emitting units. , or a color conversion material (CCM) method, etc. have been proposed, and the present invention can also be applied to such white organic electroluminescent devices.

The organic electroluminescent material according to an example of the present application may also be used in an organic electroluminescent device including quantum dots (QDs).

Additionally, the present application can provide a display device using the compound represented by Formula 1. In other words, it is possible to manufacture a display device or lighting device using the compound of the present application. Specifically, using the compounds of the present disclosure, a display device, such as a display device for a smartphone, tablet, laptop, PC, TV, or vehicle, or a lighting device, such as an outdoor or indoor lighting device, is manufactured. possible.

Hereinafter, for a detailed understanding of the present application, representative compounds of the present application are cited and the manufacturing method of the compound according to the present application and its physical properties are shown. However, the present application is not limited to the examples below.

[Example 1] Preparation of compound C-160

Preparation of compound 1-1

In a reaction vessel, benzo[b]thiophen-2-ylboronic acid (37 g, 205.05 mmol), 2-bromo-6-chlorobenzaldehyde (30 g, 136.7 mmol), tetrakis(triphenylphosphine)palladium ( 4.7 g, 4.1 mmol), potassium carbonate (47.2 g, 341.75 mmol), 400 mL of tetrahydrofuran, and 100 mL of distilled water were added and stirred at 100°C for 4 hours. After the reaction was completed, it was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound 1-1 (35 g, yield: 94%).

Preparation of Compound 1-2

Compound 1-1 (35 g, 128.32 mmol) and (methoxymethyl)triphenylphosphonium chloride (66 g, 192.48 mmol) were added to 350 mL of tetrahydrofuran in a reaction vessel, and then potassium- tert- at 0°C. 193 mL of butoxide 1M was added dropwise. After the dropwise addition, the reaction temperature was gradually raised to room temperature and stirred for an additional 2 hours. After the reaction was completed, extraction was performed with ethyl acetate and the organic layer was dried with magnesium sulfate. After removing the solvent using a rotary evaporator, the product was purified by column chromatography to obtain compound 1-2 (31 g, yield: 80%).

Preparation of compounds 1-3

After dissolving Compound 1-2 (31 g, 103.06 mmol) in chlorobenzene in a reaction vessel, 3.1 mL of Ethones reagent was slowly added dropwise. After the dropwise addition was completed, it was stirred for an additional 2 hours at room temperature. After the reaction was completed, it was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound 1-3 (24.4 g, yield: 88%).

Preparation of Compounds 1-4

In a reaction vessel, compound 1-3 (9.0 g, 29.77 mmol), bis(pinacolato)diborone (9.1 g, 35.72 mmol), tris(dibenzylideneacetone)dipalladium (1.1 g, 1.19 mmol), 2 -Add 150 mL of dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (1.0 g, 2.38 mmol), potassium acetate (8.8 g, 89.31 mmol), and 1,4-dioxane. Then, it was refluxed and stirred at 130°C for 6 hours. After the reaction was completed, it was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound 1-4 (9.0 g, yield: 84%).

Preparation of Compound C-160

In a reaction vessel, compound 1-4 (4.5 g, 12.49 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3, 5-triazine (6.6 g, 14.20 mmol), tetrakis(triphenylphosphine)palladium (0.4 g, 0.34 mmol), sodium carbonate (3.0 g, 28.38 mmol), 55 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water. After addition, it was stirred at 120°C for 4 hours. At the end of the reaction, the precipitated solid was washed with distilled water and methanol. Afterwards, it was purified by column chromatography to obtain compound C-160 (3.9 g, yield: 51%). The physical properties of synthesized compound C-160 are as follows.

[Example 2] Preparation of Compound C-5

Compound 1-4 (4.0 g, 11.1 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (4.6 g, 13.3 mmol), Pd(PPh ₃ ) ₄ (0.6 g, 0.56 mmol), and K ₂ CO ₃ (3.1 g, 22.2 mmol) were added with 5.0 mL of EtOH, 40 mL of toluene, and 11 mL of distilled water, and then refluxed and stirred for 6 hours. did. After completion of the reaction, the mixture was cooled to room temperature, stirred at room temperature, MeOH was added, and the resulting solid was filtered under reduced pressure and purified by column chromatography using MC/Hex to obtain compound C-5 (4.9 g, yield: 81%).

[Example 3] Preparation of compound C-146

Compound 1-3 (4.0 g, 14.9 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxabororane-2- 1) phenyl) -1,3,5-triazine (7.1 g, 16.4 mmol), Pd ₂ (dba) ₃ (0.7 g, 0.8 mmol), s-phos (0.6 g, 1.5 mmol), NaOtBu (3.5 g , 37.3 mmol), 80 mL of o-xylene was added and stirred under reflux for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, stirred at room temperature, MeOH was added, and the resulting solid was filtered under reduced pressure and purified by column chromatography using MC/Hex to obtain compound C-146 (3.6 g, yield: 45%).

[Example 4] Preparation of compound C-499

Compound 4-1 (5.40 g, 15.7 mmol), 2-(6-chloropyridin-3-yl)-4,6-diphenyl-1,3,5-triazine (5.41 g, 15.7 mmol) in a flask, Add 80 mL of bis(triphenylphosphine)palladium(II) dichloride (551 mg, 0.78 mmol), sodium carbonate (2.5 g, 23.5 mmol), and THF:distilled water (10:1 mixed solution) and dissolve for 6 hours. It was refluxed and stirred. After the reaction was completed, the extract was extracted with ethyl acetate and separated by column chromatography to obtain compound C-499 (3.0 g, yield: 36%).

[Example 5] Preparation of compound C-230

Synthesis of compound 5-1

In a flask, 6-chloro-3-iodo-2-methoxynaphthalene (30 g, 94.19 mmol), (2-fluorophenyl)boronic acid (13.1 g, 94.19 mmol), tetrakis(triphenylphosphine)palladium (5.4 g, 4.709 mmol), potassium carbonate (39 g, 282.5 mmol), 580 mL of toluene, 145 mL of ethanol, and 145 mL of water were added and dissolved, and then refluxed and stirred for 4 hours. After the reaction was completed, it was cooled to room temperature and extracted with ethyl acetate. Afterwards, it was separated by column chromatography to obtain compound 5-1 (18.5 g, yield: 68%).

Synthesis of compound 5-2

Compound 5-1 (18.5 g, 64.52 mmol) and pyridine hydrochloride (112 g, 967.9 mmol) were added to the flask, and then refluxed and stirred at 230°C for 3 hours. After the reaction was completed, it was cooled to room temperature and extracted with dimethyl chloride. After distillation under reduced pressure, hexane was added dropwise and filtered to obtain compound 5-2 (14.8 g, yield: 84%).

Synthesis of compound 5-3

Compound 5-2 (14.8 g, 54.27 mmol), potassium carbonate (3.75 g, 27.13 mmol), and 360 mL of dimethylformamide were added to the flask and stirred under reflux for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, water was added dropwise, and then filtered to obtain compound 5-3 (13 g, yield: 94%).

Synthesis of compound 5-4

Compound 5-3 (10 g, 39.57 mmol), bis(pinacolato)diborone (12 g, 47.48 mmol), and tris(dibenzylideneacetone)dipalladium (0) (1.4 g, 1.582 mmol) in a flask. , 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.3 g, 3.165 mmol), potassium acetate (11.6 g, 118.7 mmol), and 200 mL of 1,4-dioxane were added. The mixture was refluxed and stirred for 3 hours. After the reaction was completed, it was extracted with ethyl acetate and separated by column chromatography to obtain compound 5-4 (7.8 g, yield: 54%).

Synthesis of Compound C-230

Compound 5-4 (4.5 g, 13.07 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (5 g, 13.07 mmol), tetrakis( Triphenylphosphine)palladium (0.75 g, 0.653 mmol), potassium carbonate (5.4 g, 39.22 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of water were added and stirred under reflux for 2 hours. When the reaction was completed, it was cooled to room temperature, methanol was added dropwise, and then filtered. Afterwards, it was dissolved in dimethyl chloride and separated by column chromatography to obtain compound C-230 (3.7 g, yield: 53%).

Meanwhile, the present inventors compared the following B-type compound according to the present application with the following A-type compound not according to the present application and discovered the following facts.

A device containing a B-type compound as a red host material may have improved lifespan characteristics compared to a device containing an A-type compound as a red host material. This is not intended to be theoretically limited, but B-type compounds have longer conjugation and lower steric-hindrance energy than A-type compounds, and compounds with long conjugation stabilize electrons. This is thought to be because compounds with low steric hindrance energy are difficult to decompose at high temperatures.

Hereinafter, the characteristics of an organic electroluminescent device containing the compound of the present invention will be described for a detailed understanding of the present invention. However, the following examples only describe the characteristics of the OLED according to the present application for a detailed understanding of the present application, and the present application is not limited to the examples below.

[Device Manufacturing Examples 1 and 2] Manufacturing of OLED containing the compound according to the present application

An OLED device comprising a compound according to the present disclosure was manufactured. First, the transparent electrode ITO thin film (10Ω/□) obtained from OLED glass (manufactured by Geomatec) was ultrasonically cleaned using acetone, ethanol, and distilled water sequentially, and then stored in isopropanol before use. Next, after mounting the ITO substrate on the substrate holder of the vacuum deposition equipment, compound HI-1 is added to the cell in the vacuum deposition equipment, the chamber is evacuated until the vacuum degree reaches 10 ^-6 torr, and then a current is applied to the cell. and evaporated to deposit a first hole injection layer with a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Next, compound HT-1 was placed in a cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a 10 nm thick first hole transport layer on the second hole injection layer. Compound HT-2 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it to deposit a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was deposited thereon as follows. The compound listed in Table 1 below was placed as a host in a cell in the vacuum evaporation equipment, and compound D-71 was placed as a dopant in another cell, and then the two materials were evaporated at different rates to obtain a total amount of host and dopant. A 40 nm thick light emitting layer was deposited on the second hole transport layer by doping each dopant in an amount of 3% by weight. Subsequently, compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit a 35 nm thick electron transport layer on the emitting layer. Subsequently, compound EI-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to produce an OLED. .

[Device Manufacturing Example 3] Manufacturing of OLED containing a compound according to the present application

The first hole injection layer was deposited to a thickness of 60 nm, the first hole transport layer was deposited to a thickness of 20 nm, and compound HT-3 was used instead of compound HT-2 as the second hole transport layer to be 5 nm thick. An OLED was manufactured in the same manner as Device Manufacturing Example 1, except that a thick second hole transport layer was deposited, and the light emitting layer or electron transport layer was deposited as follows. Compound BH was added as a host to a cell in the vacuum evaporation equipment, and compound BD was added as a dopant to another cell. Then, the two materials were evaporated at different rates to add 2% by weight of each dopant based on the total amount of the host and dopant. A 20 nm thick light emitting layer was deposited on the second hole transport layer by positive doping. Subsequently, compound C-160 as an electron buffer layer (or hole blocking layer) was deposited on the emission layer to a thickness of 5 nm. In another two cells, compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 to deposit a 30 nm thick electron transport layer on the electron buffer layer (or hole blocking layer).

[Comparative Example 1] Manufacturing of OLED containing compounds not according to the present disclosure

An OLED was manufactured in the same manner as Device Preparation Example 1 except that Compound A was used as the host of the light-emitting layer.

[Comparative Example 2] Manufacturing of OLED containing compounds not according to the present disclosure

An OLED was manufactured in the same manner as Device Preparation Example 1, except that Compound B was used as the host of the light-emitting layer.

[Comparative Example 3] Manufacturing of OLED containing compounds not according to the present disclosure

Except that an electron buffer layer (or hole blocking layer) was not deposited, and a 35 nm thick electron transport layer was deposited on the light emitting layer by evaporating compound ET-1 and compound EI-1 at a rate of 1:1 as an electron transport layer. OLED was manufactured in the same manner as in Device Manufacturing Example 3.

The driving voltage based on 1,000 nit luminance of the OLED manufactured in Device Manufacturing Examples 1 and 2 and Comparative Examples 1 and 2, CIE color coordinates, and the time until the light intensity based on 5,000 nit luminance falls from 100% to 95% ( The results of lifespan (T95) are shown in Table 1 below.

[Table 1]

From Table 1, it can be seen that the organic electroluminescent device containing a compound according to the present application as a host material has a longer lifespan compared to the organic electroluminescent device containing a compound not according to the present application as a host material.

The driving voltage, luminous efficiency, and color coordinates of the OLEDs manufactured in Device Manufacturing Example 3 and Comparative Example 3 based on 1,000 nit luminance are shown in Table 2 below.

[Table 2]

From Table 2, it can be seen that the organic electroluminescent device containing the compound according to the present application as an electron buffer layer (or hole blocking layer) material exhibits higher luminous efficiency characteristics than the organic electroluminescent device not according to the present application.

Compounds used in the device manufacturing examples and comparative examples are shown in Table 3 below.

[Table 3]

Claims (3)

Organic electroluminescent compound represented by Formula 1:
[Formula 1]

In Formula 1,
X is O or S;
R ₁ to R ₄ are each independently hydrogen or deuterium;
R ₆ and R ₇ are fused with each other in the formula 2 below to form a ring,
[Formula 2]

R ₅ and R ₈ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;
R ₉ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, , provided that at least one of R ₉ to R ₁₂ is ego;
L is (C11-C18)arylene substituted or unsubstituted with deuterium;
ETU is It is displayed as
R is each independently (C6-C18)aryl substituted or unsubstituted with deuterium, dibenzofuranyl substituted or unsubstituted with deuterium, dibenzothiophenyl substituted or unsubstituted with deuterium, or a combination thereof, They may be the same or different from each other. Organic electroluminescent compound represented by Formula 1:
[Formula 1]

In Formula 1,
X is O or S;
R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) may be heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or may be connected to each other to form a ring; However, at least one of R ₁ to R ₄ is halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 members) ) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, or are connected to each other to form a ring;
R ₆ and R ₇ are fused with each other in the formula 2 below to form a ring,
[Formula 2]

R ₅ and R ₈ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino;
R ₉ to R ₁₂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) heteroaryl, substituted or unsubstituted silyl, or substituted or unsubstituted amino, , provided that at least one of R ₉ to R ₁₂ is ego;
L is a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene;
ETU is

It is displayed as
R is each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3) -C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted silyl, or substituted or unsubstituted amino. An organic electroluminescent compound selected from the group consisting of the following compounds.