KR20210010406A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device including the same. When the compound is used in an organic material layer of the organic light emitting device, lifespan characteristics thereof can be improved.

Description

Compound and organic light-emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present invention claims the benefit of the filing date of Korean Patent No. 10-2019-0087636 filed with the Korean Intellectual Property Office on July 19, 2019, the entire contents of which are incorporated herein.

The present specification relates to a compound and an organic light emitting device including the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

Development of a new material for the organic light emitting device as described above is continuously required. In particular, for blue organic materials, fluorescent materials are used due to the problem of lifespan, but technologies such as triplet-triplet annihilation (TTA) or triplet excitons using phosphorescent materials are used due to the low internal quantum efficiency of fluorescent materials. . Commercially available blue fluorescent organic materials have a structure with pyrene as a core, but have a wide ring width and thus may have disadvantages in manufacturing a top light emitting device. Therefore, the development of a blue organic material having a narrow ring width and high efficiency is required.

US Patent Application Publication No. 2004-0251816

The present specification provides a compound and an organic light emitting device including the same.

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

X is N or CR,

Z ₁ and Z ₂ are the same as or different from each other, and each independently O or CR'R",

R, R'and R" are the same as or different from each other, and each independently hydrogen, hydroxy group, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group , Or a substituted or unsubstituted amine group,

R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted hetero It is an aryl group, or may be combined with an adjacent substituent to form a substituted or unsubstituted aromatic ring,

a and b are integers from 0 to 4,

When a or b is plural, the substituents in parentheses are the same as or different from each other.

In addition, the present invention is a first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light emitting device.

The compound of the present specification has a structure in which nitrogen serving as a donor and ketone serving as an acceptor are bound together, and HOMO LUMO is separated in the opposite direction in the molecule. Through this, it is possible to develop a blue fluorescent material having a narrow half width and high efficiency.

1 and 2 illustrate an organic light-emitting device according to an exemplary embodiment of the present specification.

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

Compounds having the same structure as the following Y1, Y2, and Y3 have been developed, but Y1 has a high molecular weight to be used in an organic light emitting device, making it difficult to fabricate a device using it, and Y2 is the lifespan of the organic light emitting device due to functional groups such as Na and Br. It causes shortening of and Y3 has a disadvantage in that a short lifespan is caused due to instability of the molecular structure.

The present specification provides a compound represented by Formula 1 that compensates for the disadvantages of the compounds Y1 to Y3.

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

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. For example, the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

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

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

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

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkyl heteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; N-phenylnaphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but are not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRxRyRz, wherein Rx, Ry and Rz are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyldimethylsilyl group; Propyldimethylsilyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. More specifically, it is preferably 6 to 20 carbon atoms. Specifically, the monocyclic aryl group is a phenyl group; Biphenyl group; It may be a terphenyl group or the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferred that it has 10 to 30 carbon atoms, and more specifically, it is preferred that it has 10 to 20 carbon atoms. Specifically, the polycyclic aryl group includes a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenalenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group or the like, but is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

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

In the present specification, the heteroaryl group includes one or more atoms other than carbon, that is, heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrole group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyrido pyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazolyl group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline; Isoxazolyl group; Thiadiazolyl group; There may be a phenothiazinyl group and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aromatic ring is the same as the definition of the aryl group except that it is not monovalent.

In the exemplary embodiment of the present specification, X is N.

In the exemplary embodiment of the present specification, X is CR.

In the exemplary embodiment of the present specification, Z ₁ and Z ₂ are O.

In the exemplary embodiment of the present specification, Z ₁ and Z ₂ are CR'R".

In the exemplary embodiment of the present specification, Z ₁ is O, and Z ₂ is CR'R".

In the exemplary embodiment of the present specification, Z ₂ is O, and Z ₁ is CR'R".

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 2 to 5.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, R, R ₁ , R ₂ , a and b are as defined in Formula 1,

Ra to Rd are the same as or different from each other, and each independently hydrogen, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted It is an amine group.

In the exemplary embodiment of the present specification, R, R'and R" are the same as or different from each other, and each independently hydrogen, a hydroxy group, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted Or an unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, or an amine group substituted with a C6-C30 aryl group.

In the exemplary embodiment of the present specification, R, R'and R" are the same as or different from each other, and each independently hydrogen, a hydroxy group, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted Or an unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group containing N, O, or S.

In the exemplary embodiment of the present specification, R, R'and R" are the same as or different from each other, and each independently hydrogen, hydroxy group, nitrile group, halogen group, methyl group, ethyl group, propyl group, isopropyl group, butyl group , Terbutyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracene group, phenanthrene group, triphenylene group, fluorene group substituted with an alkyl group or aryl group, carbazole group, dibenzofuran group, or dibenzothiophene It is.

In the exemplary embodiment of the present specification, R is an amine group substituted with hydrogen, a hydroxy group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R is an amine group substituted with hydrogen, a hydroxy group, a nitrile group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R is an amine group substituted with hydrogen, a hydroxy group, a nitrile group, or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R is hydrogen; Hydroxy group; Nitrile group; Or an amine group substituted with a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, an anthracene group, a phenanthrene group, or a fluorene group.

In an exemplary embodiment of the present specification, R is hydrogen; Hydroxy group; Nitrile group; Or an amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group.

In an exemplary embodiment of the present specification, R is hydrogen; Hydroxy group; Nitrile group; Or a phenyl group or a biphenyl group substituted amine group.

In an exemplary embodiment of the present specification, R is hydrogen; Hydroxy group; Nitrile group; Or a diphenylamine group.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms A biphenyl group; a naphthyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; an anthracene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; a phenanthrene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; A fluorene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; Or a triphenylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms A biphenyl group; Or a naphthyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted amine group, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or may be combined with an adjacent substituent to form a substituted or unsubstituted aromatic ring.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Nitrile group; An alkyl group having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or may be combined with an adjacent substituent to form a substituted or unsubstituted aromatic ring.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Nitrile group; Methyl group; Terbutyl group; A substituted or unsubstituted phenyl group; An amine group substituted with a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, or an anthracene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted phenoxazine group; A substituted or unsubstituted phenothiazine group; A substituted or unsubstituted dihydrophenazine group; Or a substituted or unsubstituted dihydroacridine group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or an alkyl group; An amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; A carbazole group substituted with an alkyl group or an aryl group; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with an aryl group; Or a dihydroacridine group unsubstituted or substituted with an alkyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or an alkyl group having 1 to 10 carbon atoms; An amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; A carbazole group substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a dihydroacridine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or a methyl group; An amine group substituted with a phenyl group; A carbazole group substituted with a methyl group or a terbutyl group; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with a phenyl group; Or a dihydroacridine group unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as each other, and hydrogen; Nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or an alkyl group having 1 to 10 carbon atoms; An amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; A carbazole group substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a dihydroacridine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as each other, and hydrogen; Nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or a methyl group; An amine group substituted with a phenyl group; A carbazole group substituted with a methyl group or a terbutyl group; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with a phenyl group; Or a dihydroacridine group unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, R ₁ is hydrogen, R ₂ is a nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or an alkyl group having 1 to 10 carbon atoms; An amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; A carbazole group substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a dihydroacridine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ is hydrogen, R ₂ is a nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or a methyl group; An amine group substituted with a phenyl group; A carbazole group substituted with a methyl group or a terbutyl group; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with a phenyl group; Or a dihydroacridine group unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, R ₂ is hydrogen, R ₁ is a nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or an alkyl group having 1 to 10 carbon atoms; An amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; A carbazole group substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a dihydroacridine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R ₂ is hydrogen, R ₁ is a nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or a methyl group; An amine group substituted with a phenyl group; A carbazole group substituted with a methyl group or a terbutyl group; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with a phenyl group; Or a dihydroacridine group unsubstituted or substituted with a methyl group.

In the exemplary embodiment of the present specification, R ₁ is hydrogen, and R ₂ is an amine group substituted with an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ is hydrogen, and R ₂ is an amine group substituted with a phenyl group.

In the exemplary embodiment of the present specification, R ₂ is hydrogen, and R ₁ is an amine group substituted with an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₂ is hydrogen, and R ₁ is an amine group substituted with a phenyl group.

In the exemplary embodiment of the present specification, R ₁ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and R ₂ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ is a methyl group or terbutyl group, and R ₂ is a methyl group; Terbutyl group; Or a phenyl group unsubstituted or substituted with a nitrile group or a methyl group.

In the exemplary embodiment of the present specification, R ₂ is a methyl group or terbutyl group, and R ₁ is a methyl group; Terbutyl group; Or a phenyl group unsubstituted or substituted with a nitrile group or a methyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ may be combined with an adjacent substituent to form an aromatic ring having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ may be combined with an adjacent substituent to form a benzene ring.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Nitrile group; Methyl group; Terbutyl group; A phenyl group unsubstituted or substituted with a nitrile group or an alkyl group having 1 to 10 carbon atoms; An amine group substituted with a phenyl group, a biphenyl group, or a naphthyl group; A carbazole group substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; Phenox camera; Phenothiazine group; A dihydrophenazine group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a dihydroacridine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or may be combined with an adjacent substituent to form an aromatic ring having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the compound of Formula 1 is selected from the following structures.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

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

The organic light-emitting device of the present invention includes a first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers may include the aforementioned compound.

For example, the structure of the organic light-emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

1 illustrates a structure of an organic light-emitting device in which an anode 2, an emission layer 3, and a cathode 4 are sequentially stacked on a substrate 1.

1 illustrates an organic light-emitting device and is not limited thereto.

Figure 2 shows the anode (2), the hole injection layer (5), the first hole transport layer (6), the second hole transport layer (7), the light emitting layer (3), the electron injection layer and the electron transport layer (8) on the substrate (1). And a structure of an organic light-emitting device in which the cathode 4 is sequentially stacked is illustrated. The compound of the present specification is preferably included in the light emitting layer 3, but is not limited thereto.

In one embodiment of the present invention, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 1.

In an exemplary embodiment of the present invention, the light emitting layer includes a host and a dopant.

In an exemplary embodiment of the present invention, the emission layer includes the compound of Formula 1 as a dopant.

In an exemplary embodiment of the present invention, the emission layer includes a host and a dopant in a mass ratio of 99.9:0.01 to 80:20.

In one embodiment of the present invention, the emission layer includes a host and a dopant in a mass ratio of 99:1 to 80:20.

In an exemplary embodiment of the present invention, the emission layer includes a host and a dopant in a mass ratio of 99:1 to 90:10.

In one embodiment of the present invention, the emission layer includes an anthracene-based compound as a host.

The organic light-emitting device according to the exemplary embodiment of the present specification includes an emission layer, and the emission layer includes a compound represented by Formula 1 and a compound represented by Formula H below.

[Formula H]

In the formula H,

L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

k is 0 or 1.

In the exemplary embodiment of the present specification, when k is 0, the position of -L23-Ar23 is connected to hydrogen.

In the exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group containing N, O, or S.

In the exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; C6-C30 arylene group; Or a C2-C30 heteroarylene group including N, O, or S, and the arylene group or heteroarylene group is substituted or provided with a C1-C10 alkyl group, a C6-C30 aryl group, or a C2-C30 heteroaryl group. It is bright.

In the exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a C6-C30 aryl group unsubstituted or substituted with deuterium; Or a C2-C30 heteroaryl group unsubstituted or substituted with deuterium.

In the exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.

In the exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted deuterium monocyclic to tetracyclic aryl group; Or it is a monocyclic to 4 ring heteroaryl group substituted or unsubstituted with deuterium.

In the exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

In the exemplary embodiment of the present specification, Ar21 and Ar22 are different from each other.

In the exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is an aryl group unsubstituted or substituted with deuterium.

In the exemplary embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.

In the exemplary embodiment of the present specification, R21 to R27 are the same as or different from each other, and each independently hydrogen or deuterium.

In an exemplary embodiment of the present specification, R21 to R27 are hydrogen.

In the exemplary embodiment of the present specification, k is 0.

In an exemplary embodiment of the present invention, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer contains the compound of Formula 1 I can.

In an exemplary embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound of Formula 1 I can.

In an exemplary embodiment of the present invention, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the compound of Formula 1 above.

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. After depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an organic material layer including the compound of Formula 1 are formed thereon, and then a material that can be used as a cathode is deposited thereon. It can be produced by In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode, has the ability to transport holes, and as a hole injection material, a material capable of well injecting holes from the anode at a low voltage, and is a high-occupied hole injection material. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

In an exemplary embodiment of the present invention, the organic light-emitting device includes at least one hole transport layer.

In an exemplary embodiment of the present invention, the organic light emitting device includes a first hole transport layer and a second hole transport layer.

In an exemplary embodiment of the present invention, an arylamine compound is used as a material for the first hole transport layer and the second hole transport layer.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers is formed using the compound.

The present specification also provides a method of manufacturing an organic light-emitting device formed using the compound.

Dopant materials include aromatic compounds, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted The arylamine is a compound in which at least one arylvinyl group is substituted, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows. An anthracene-based compound may be used as the electron transport layer material, and the anthracene-based compound may be substituted with an N-containing heteroaryl group such as benzimidazole, and may be used together with lithium quinolate (Liq) in a mass ratio of 1:1.

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

A layer for simultaneously injecting and transporting electrons may be used separately from the electron transport layer and the electron injection layer. The electron injection and transport layer may be configured in addition to the electron transport layer and the electron injection layer, or may be configured instead of the electron transport layer or the electron injection layer. For example, the organic light emitting device may include all of an electron injection layer, an electron transport layer, an electron injection and transport layer, only one layer, or any two layers.

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

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

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

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.

The manufacturing method of the compound of Formula 1 and the manufacturing of an organic light emitting device using the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

In the following reaction scheme, various types of intermediates can be synthesized according to the type and number of substituents appropriately selecting a known starting material by a person skilled in the art. As for the reaction type and reaction conditions, those known in the art may be used.

<Synthesis Example>

Synthesis Example 1. Synthesis of Compound 1

Synthesis of Intermediate A-1

Compound A-1-1 dimethyl 2-(bis(3-bromophenyl)amino)isophthalate (3.61g, 10mmol) and sodium hydroxide (2.0g, 50mmol) were dissolved in ethanol:water 1:1 100ml solvent for 12 hours It was heated to reflux during the period. Acidified with concentrated hydrochloric acid and precipitated, which was collected by vacuum filtration, and then dried overnight (80°C) in an oven to obtain 3.26 g of compound A-1-2. Compound A-1-2, 2-(bis(3-bromophenyl)amino)isophthalic acid (2.67 g, 8 mmol) was dried in a reflux condenser with a 3-neck round bottom flask equipped with a magnetic stir bar and a drying tube. Disperse in dichloromethane (80mL). Two drops of N-dimethylformamide and oxalyl chloride (1.5 mL, 17.6 mmol) were added. The reaction was heated to reflux for 0.5 hours. Tin chloride (2.0 mL, 17.6 mmol) was added and the reaction was refluxed for an additional 3 hours. The reaction mixture was added dropwise to an aqueous sodium hydroxide solution (~1M) and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated. Subsequently, the crude was subjected to flash chromatography with a DCM:ether 3:1 eluent to obtain 8 g of a bright yellow-green solid A-1 1. MS: [M+H]+ = 452.

Synthesis of compound 1

Compound A-1 (1.02g, 2mmol), 9,9-dimethyl-9,10-dihydroacridine (0.94g, 4.5mmol), Pd ₂ (dba) ₃ (0.15g, 0.16mmol), tri- Thibutylphosphonium tetrafluoroborate (0.046g, 0.16mmol) and sodium thibutoxide (0.96g, 10mmol) were dissolved in toluene under argon. After stirring at 110° C. for 12 hours, the reaction was cooled at room temperature. The reaction mixture was filtered through a pad of Celite, washed with water and brine, and concentrated by evaporation. The crude product was subjected to column chromatography with an eluent of 1:4 ether:dichloromethane. After stirring with refluxed ethanol, it was filtered and dried in a vacuum oven to obtain 1.39 g of compound 1. MS: [M+H]+ = 711.

Synthesis Example 2. Synthesis of Compound 2

In the synthesis of compound 1, 9,9-dimethyl-9,10-dihydroacridine (0.94g) was prepared in the same manner except that 9H-carbazole (0.81g) was used to obtain compound 2. MS: [M+H]+ =627.

Synthesis Example 3. Synthesis of Compound 3

In the synthesis of compound 1, 9,9-dimethyl-9,10-dihydroacridine (0.94g) was prepared in the same manner except that 3,6-dimethyl-9H-carbazole (0.8g) was used. Compound 3 was obtained. MS: [M+H]+ = 683.

Synthesis Example 4. Synthesis of Compound 4

In the synthesis of compound 1, 9,9-dimethyl-9,10-dihydroacridine (0.94g) was prepared in the same manner except that diphenylamine (0.85g) was used to obtain compound 4. MS: [M+H]+ = 631.

Synthesis Example 5. Synthesis of Compound 5

In the synthesis of compound 1, in the same manner as 9,9-dimethyl-9,10-dihydroacridine (0.94 g), except that 5-phenyl-5,1-dihydrophenazine (0.96 g) was used. Prepared to obtain compound 5. MS: [M+H]+ = 809.

Synthesis Example 6. Synthesis of Compound 6

In the synthesis of compound 1, 9,9-dimethyl-9,10-dihydroacridine (0.94g) was prepared in the same manner, except that 10H-phenoxazine (0.83g) was used to obtain compound 6. MS: [M+H]+ = 691.

Synthesis example 7. Synthesis of compound 7

In the synthesis of intermediate A-1, instead of dimethyl 2-(bis(3-bromophenyl)amino)isophthalate (3.61g), dimethyl-2-(bis(3-tibutyl)phenyl)amino)isophthalate (3.03g) Except for using, it was prepared in the same manner to obtain compound 7. MS: [M+H]+ = 409.

Synthesis Example 8. Synthesis of Compound 8

Synthesis of Intermediate B-1

In the synthesis of Intermediate A-1, instead of dimethyl 2-(bis(3-bromophenyl)amino)isophthalate (3.61 g), dimethyl 2-(bis(4-bromophenyl)amino)isophthalate (3.76 g) was added. It was prepared in the same manner except for using, to obtain the intermediate B-1. MS: [M+H]+ = 452.

Synthesis of compound 8

Intermediate B-1 3,11-dibromoquinolino[3,2,1-di]acridine-5,9-dione (3.44g) and 1-aryl bromide (3.4g), potassium cyanide (5.1g ) Was dissolved in nitrile acetone (0.94mL/mmol), Bu ₃ SnCl, Pd2(dba)3, and t-Bu ₃ P were added and reacted at 80° C. for 17 hours to obtain compound 8. MS: [M+H]+ = 347.

Synthesis Example 9. Synthesis of Compound 9

Intermediate B-1 3,11-dibromoquinolino[3,2,1-di]acridine-5,9 dione (3.5g) and 4-cyanophenylboronic acid (7.7g), sodium hydroxide (12g) was dissolved in a toluene:water 1:1 solvent and reacted by adding a Pd catalyst to obtain compound 9. MS: [M+H]+ = 499.

Synthesis Example 10. Synthesis of Compound 10

Compound 10 was obtained in the same manner as in the synthesis of compound 9, except that o-tolylboronic acid (7.7g) was used instead of 4-cyanophenylboronic acid (7.7g). MS: [M+H]+ = 477.

Synthesis Example 11. Synthesis of Compound 11

Synthesis of Intermediate C-1

In the synthesis of intermediate A-1, instead of dimethyl 2-(bis(3-bromophenyl)amino)isophthalate (3.61g), dimethyl 4-(bis(3-bromophenyl)amino)pyridine-3,5-dicarboxyl Compound C-1 was obtained by the same preparation except that rate (3.4g) was used. MS: [M+H]+ = 454.

Synthesis of compound 11

Compound C-1 (1.03g, 2mmol), diphenylamine (0.85g), Pd ₂ (dba) ₃ (0.15g, 0.16mmol), tri-tibutylphosphonium tetrafluoroborate (0.046g, 0.16mmol) , Sodium thibutoxide (0.96g, 10mmol) was dissolved in toluene under argon. After stirring at 110° C. for 12 hours, the reaction was cooled at room temperature. The reaction mixture was filtered through a pad of Celite, washed with water and brine, and concentrated by evaporation. The crude product was subjected to column chromatography with an eluent of 1:4 ether:dichloromethane. After stirring with reflux ethanol, it was filtered and dried in a vacuum oven to obtain 1.33 g of compound 11. MS: [M+H]+ = 632.

Synthesis example 12. Synthesis of compound 12

In the synthesis of compound 11, instead of diphenylamine (0.85g), 9H-carbazole (0.81g) was used in the same manner to obtain compound 12. MS: [M+H]+ =628.

Synthesis example 13. Synthesis of compound 13

In the synthesis of compound 11, instead of diphenylamine (0.85g), 3,6-dimethyl-9H-carbazole (0.8g) was used in the same manner, except that compound 13 was obtained. MS: [M+H]+ = 684.

Synthesis example 14. Synthesis of compound 14

Synthesis of Intermediate D-1

In the synthesis of intermediate A-1, instead of dimethyl 2-(bis(3-bromophenyl)amino)isophthalate (3.61 g), dimethyl 2-(bis(3-bromophenyl)amino)-5-cyanoisophthalate ( 2.77g) was prepared in the same manner, except that the compound D-1 was obtained. MS: [M+H]+ = 478.

Synthesis of compound 14

Compound D-1 (1.1g, 2mmol), diphenylamine (0.85g), Pd ₂ (dba) ₃ (0.15g, 0.16mmol), tri-tibutylphosphonium tetrafluoroborate (0.046g, 0.16mmol) , Sodium thibutoxide (0.96g, 10mmol) was dissolved in toluene under argon. After stirring at 110° C. for 12 hours, the reaction was cooled at room temperature. The reaction mixture was filtered through a pad of Celite, washed with water and brine, and concentrated by evaporation. The crude product was subjected to column chromatography with an eluent of 1:4 ether:dichloromethane. After stirring with reflux ethanol, it was filtered and dried in a vacuum oven to obtain 1.7 g of compound 14. MS: [M+H]+ = 656.

Synthesis Example 15. Synthesis of Compound 15

In the synthesis of compound 14, except that 9H-carbazole (0.93g) was used instead of diphenylamine (0.85g), compound 15 was obtained. MS: [M+H]+ = 652.

When the preparation formula described in the examples of the present specification and the intermediates are appropriately combined based on common technical knowledge, all of the compounds of Formula 1 described in the present specification can be prepared.

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1300Å was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following compound HAT was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer. On it, 1000 Å of the following compound HT-A was vacuum-deposited as a first hole transport layer, and 100 Å of the following compound HT-B was subsequently deposited as a second hole transport layer. BH-1 as a host and Compound 1 as a dopant were vacuum-deposited at a weight ratio of 95:5 to form a light emitting layer having a thickness of 200 Å.

Then, as a layer for simultaneous electron injection and transport, the following compound ET-A and the following compound Liq were deposited in a 1:1 ratio (300Å by weight ratio, and lithium fluoride (LiF) and 1,000Å in a thickness of 10Å sequentially By depositing aluminum to a thickness to form a cathode, an organic light emitting device was manufactured.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 2.0 Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 1 × 10 ⁻ Maintaining ⁷ to 5 Х 10 ^-8 torr, an organic light emitting device was manufactured.

Example 2 to 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the dopant compound shown in Table 1 below was used instead of Compound 1 as the light emitting layer material in Example 1.

Comparative Examples 1 and 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the dopant compound shown in Table 1 below was used instead of Compound 1 as the light emitting layer material in Example 1.

The organic light-emitting devices fabricated in Examples 1 to 5 and Comparative Examples 1 and 2 were used with a Keithley 2635B system source meter and a PR670 detector at a current density of 10 mA/cm ² at the maximum peak position of the EL spectrum and the full width at half maximum. (FWHM), the luminous efficiency was measured, and the results are shown in Table 1 below.

Dopant
(Luminescent layer) 10mA / cm ² EL max peak
(nm) FWHM
(nm) Luminous efficiency
(Cd/A) Example 1 One 465 17 6.8 Example 2 7 467 15 6.2 Example 3 8 466 15 6.5 Example 4 12 464 17 6.2 Example 5 14 464 19 6.6 Comparative Example 1 BD-1 473 22 0.4 Comparative Example 2 BD-2 455 11 4.3

As shown in Table 1, the devices of Examples 1 to 5 using the compound having the structure of Formula 1 have higher efficiency than the devices of Comparative Examples 1 to 2. Compound BD-1 of Comparative Example 1 has a functional group such as Br. As a result, the reactivity of the compound increases, making it unstable. It can be seen that applying this to an organic light emitting device causes a significant decrease in efficiency of the device.

Compound BD-2 of Comparative Example 1 has an additional ring formed in its core structure, unlike the compound of Formula 1 in the present specification. The molecular structure becomes unstable due to the repulsive force between atoms constituting the core, and when used in an organic light emitting device, the efficiency decreases.

In the case of compounds 1, 7, 8, 12, and 14 of Formula 1 of the present specification, unlike compounds BD-1 and BD-2, the stability of molecules in the substituent and core structure is increased, so that luminous efficiency is significantly improved. have.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: first hole transport layer
7: second hole transport layer
8: electron injection and transport layer

Claims (11)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X is N or CR,
Z ₁ and Z ₂ are the same as or different from each other, and each independently O or CR'R",
R, R'and R" are the same as or different from each other, and each independently hydrogen, hydroxy group, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group , Or a substituted or unsubstituted amine group,
R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted hetero It is an aryl group, or may be combined with an adjacent substituent to form a substituted or unsubstituted aromatic ring,
a and b are integers from 0 to 4,
When a or b is plural, the substituents in parentheses are the same as or different from each other. The compound of claim 1, wherein Z ₁ and Z ₂ are O. The compound of claim 1, wherein Z ₁ and Z ₂ are CR'R". The compound of claim 1, wherein Z ₁ is O, and Z ₂ is CR'R". The compound of claim 1, wherein X is N. The compound of claim 1, wherein X is CR. The compound of claim 1, wherein R is an amine group substituted with hydrogen, a hydroxy group, a nitrile group, or an aryl group having 6 to 30 carbon atoms. The method according to claim 1, wherein R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted The aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a compound capable of forming a substituted or unsubstituted aromatic ring by bonding with an adjacent substituent. The compound of claim 1, wherein Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound of any one of claims 1 to 9 Light-emitting element. The organic light-emitting device of claim 10, wherein the organic material layer includes an emission layer, and the emission layer includes the compound.

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