JP2019527198A - Heterocyclic compound and organic light emitting device including the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of Formula 1 and an organic light emitting device including the same.

Description

  This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0083728 filed with the Korean Patent Office on July 1, 2016, the entire contents of which are incorporated herein.

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

  The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light emission phenomenon is as follows. When an organic material layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are respectively injected from the cathode and the anode into the organic material layer. Electrons and holes injected into the organic layer are recombined to form excitons, which emit light while falling back to the ground state. An organic light emitting device using such a principle generally includes a cathode, an anode, and an organic material layer positioned between them, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, And an organic material layer including an electron injection layer.

  In order to improve the performance, lifetime or efficiency of organic light emitting devices, the development of organic thin film materials continues to be required.

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

前記化学式１において、
Ｒ５〜Ｒ８は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；アリールオキシ基；アルキルチオキシ基；アリールチオキシ基；アルキルスルホキシ基；アリールスルホキシ基；シリル基；ホウ素基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のアリール基；置換もしくは非置換のアルアルキル基；置換もしくは非置換のアルキルアミン基；置換もしくは非置換のアラルキルアミン基；置換もしくは非置換のヘテロアリールアミン基；置換もしくは非置換のアリールアミン基；置換もしくは非置換のアリールヘテロアリールアミン基；置換もしくは非置換のアリールホスフィン基；または置換もしくは非置換のヘテロ環基であり、
Ｌ１およびＬ２は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換のアリーレン基；または置換もしくは非置換の２価のヘテロ環基であり、
Ａｒ１は、置換もしくは非置換の炭化水素環基；または置換もしくは非置換のヘテロ環基であり、
Ｒ１〜Ｒ４は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロ環基であり、
ａおよびｂはそれぞれ、０〜４の整数であり、
ｃおよびｄは、０〜３の整数であり、
ａ〜ｄがそれぞれ２以上の場合、括弧内の置換基は、互いに同一または異なり、
ｎ１およびｎ２はそれぞれ、０または１であり、
ｎ１およびｎ２のうちの１以上は、１の整数であり、
Ｘ１およびＸ２は、水素であるか、互いに直接結合する。 One embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.
[Chemical Formula 1]

In Formula 1,
R5 to R8 are the same or different from each other, and are independently hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkylsulfoxy group, aryl Silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aralkyl A substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted heterocyclic group,
L1 and L2 are the same or different from each other and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group;
Ar1 is a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group;
R1 to R4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
a and b are each an integer of 0 to 4,
c and d are integers of 0 to 3,
when a to d are each 2 or more, the substituents in parentheses are the same or different from each other;
n1 and n2 are each 0 or 1,
1 or more of n1 and n2 is an integer of 1,
X1 and X2 are hydrogen or are directly bonded to each other.

  One embodiment of the present specification includes a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode. One or more layers of include an organic light-emitting device including the heterocyclic compound.

  The heterocyclic compound described in this specification can be used as a material for an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. The compounds described herein can be used as a hole injection, hole transport, hole injection and hole transport, electron suppressor, light emission, hole suppressor, electron transport or electron injection material.

An example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 is shown. An example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 is shown. 2 is a diagram showing NMR data of Compound 1. FIG. 4 is a diagram showing NMR data of Compound 2. FIG. FIG. 4 is a graph showing Mass data of Compound 10.

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

前記化学式１において、
Ｒ５〜Ｒ８は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；アリールオキシ基；アルキルチオキシ基；アリールチオキシ基；アルキルスルホキシ基；アリールスルホキシ基；シリル基；ホウ素基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のアリール基；置換もしくは非置換のアルアルキル基；置換もしくは非置換のアルキルアミン基；置換もしくは非置換のアラルキルアミン基；置換もしくは非置換のヘテロアリールアミン基；置換もしくは非置換のアリールアミン基；置換もしくは非置換のアリールヘテロアリールアミン基；置換もしくは非置換のアリールホスフィン基；または置換もしくは非置換のヘテロ環基であり、
Ｌ１およびＬ２は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換のアリーレン基；または置換もしくは非置換の２価のヘテロ環基であり、
Ａｒ１は、置換もしくは非置換の炭化水素環基；または置換もしくは非置換のヘテロ環基であり、
Ｒ１〜Ｒ４は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロ環基であり、
ａおよびｂはそれぞれ、０〜４の整数であり、
ｃおよびｄは、０〜３の整数であり、
ａ〜ｄがそれぞれ２以上の場合、括弧内の置換基は、互いに同一または異なり、
ｎ１およびｎ２はそれぞれ、０または１であり、
ｎ１およびｎ２のうちの１以上は、１の整数であり、
Ｘ１およびＸ２は、水素であるか、互いに直接結合する。 One embodiment of the present specification provides a compound represented by Formula 1 below.
[Chemical Formula 1]

In Formula 1,
R5 to R8 are the same or different from each other, and are independently hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkylsulfoxy group, aryl Silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aralkyl A substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted heterocyclic group,
L1 and L2 are the same or different from each other and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group;
Ar1 is a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group;
R1 to R4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
a and b are each an integer of 0 to 4,
c and d are integers of 0 to 3,
when a to d are each 2 or more, the substituents in parentheses are the same or different from each other;
n1 and n2 are each 0 or 1,
1 or more of n1 and n2 is an integer of 1,
X1 and X2 are hydrogen or are directly bonded to each other.

  Examples of the substituent will be described below, but are not limited thereto.

  In the present specification, the term “substitution” means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substituted position is the position at which the hydrogen atom is substituted, that is, the substitution The position is not limited as long as the group can be substituted. When two or more groups are substituted, the two or more substituents may be the same or different from each other.

  In this specification, the term “substituted or unsubstituted” refers to deuterium; halogen group; nitrile group; nitro group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted aryl group; Substituted with one or more substituents selected from the group consisting of unsubstituted heterocyclic groups, or substituted with a substituent to which two or more of the exemplified substituents are linked, or It means that it does not have any substituent. For example, “a substituent in which two or more substituents are linked” is an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, or an alkyl group. May be an aryl group formed.

  As used herein, an “adjacent” group refers to a substituent substituted by an atom directly linked to the atom to which the substituent is substituted, a substituent that is sterically closest to the substituent, or the It can mean other substituents in which the substituent is replaced by a substituted atom. For example, two substituents substituted in the ortho position on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as “adjacent” groups to each other. .

は、結合する部位を意味する。 In this specification,

Means a binding site.

  In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

In the present specification, the silyl group may be represented by a chemical formula of —SiR _a R _b R _c , wherein each of the R _a , R _b, and R _c is hydrogen; a substituted or unsubstituted alkyl group; It may be an unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. However, it is not limited to these.

In the present specification, a boron group may be represented by a chemical formula of —BR _a R _b , wherein R and R _b are each hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. There may be. Specific examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

  In the present specification, the alkyl group may be linear or branched, and the number of carbons is not particularly limited, but may be 1 to 50. According to one embodiment, the number of carbons is 1 It may be ~ 30. According to another embodiment, the carbon number may be 1-20. 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-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-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- Methylheptyl group, 1-ethyl - propyl, 1,1-dimethyl - propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group there are such as, but not limited to.

  In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group may have 3 to 30 carbon atoms, and according to another embodiment, 3 to 20 carbon atoms. Specifically, 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 a straight chain, a branched chain or a ring chain. Although carbon number of an alkoxy group is not specifically limited, A C1-C20 thing is preferable. Specifically, 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 The group may be a p-methylbenzyloxy group, but is not limited thereto.

In this specification, an amine group consists of —NH ₂ ; an alkylamine group; an N-arylalkylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group. The number of carbon atoms may be selected from the group, and the number of carbon atoms is not particularly limited. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, Examples include, but are not limited to, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, and triphenylamine group.

  In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but may be 2 to 40. There may be. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group and 3-methyl. -1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2- Examples include phenyl-2- (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, and styryl group. Not.

  In the present specification, the alkylamine group is not particularly limited in carbon number, but may be 1 to 40, and may be 1 to 20 according to one embodiment. Specific examples of the alkylamine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group. , Phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, etc., but are not limited thereto.

  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 including 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.

  Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine group, 9- Examples include, but are not limited to, methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, and triphenylamine group.

  In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.

  In the present specification, an arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

  In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The aryl phosphine 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.

  In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but may be 6 to 60 carbon atoms. According to one embodiment, the number of carbon atoms may be 6 to 30. Alternatively, according to another embodiment, it may be 6-20. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

  When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but may be 10 to 60 carbon atoms, and may be 6 to 30 according to one embodiment, It may be 20. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrycenyl group, fluorenyl group, or the like, but is not limited thereto.

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

などになってもよい。ただし、これらに限定されるものではない。 When the fluorenyl group is substituted,

It may be. However, it is not limited to these.

  In the present specification, the heterocyclic group includes one or more atoms that are not carbon and hetero atoms, and specifically, the hetero atoms are selected from the group consisting of O, N, Se, and S. One or more atoms may be included. The number of carbon atoms of the heterocyclic group is not particularly limited, but may be 2 to 60 carbon atoms, and according to one embodiment, may be 2 to 30 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, pyridazine Group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzoquinolinyl Group, benzopyridazinyl group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, i There are oxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, and dibenzofuranyl group, benzoimidazonaphthyrin group, phenanthroimidazole group, benzoimidazophenanthridine group, etc. It is not something.

  The heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic.

  In the present specification, the hydrocarbon ring may be aliphatic, aromatic, or a condensed ring of aliphatic and aromatic, and the cycloalkyl group or aryl group except for those that are not monovalent groups. May be selected from the examples. The heterocyclic group may be aliphatic, aromatic, or a condensed ring of aliphatic and aromatic, and is selected from the examples of the heterocyclic group except for those that are not monovalent groups. Also good.

  In the present specification, an aryloxy group, arylthioxy group, arylsulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group The description regarding the aryl group mentioned above is applicable to an aryl group.

  In the present specification, the above-described explanation of the alkyl group can be applied to the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group, and the alkyl group in the alkylamine group.

  In this specification, the heteroaryl group in a heteroaryl group, heteroarylamine group, and arylheteroarylamine group can apply the description regarding the heterocyclic group mentioned above.

  In the present specification, the alkenyl group in the arylalkenyl group and the arylalkenyl group can be applied to the explanation regarding the alkenyl group described above.

  In this specification, the description regarding the alkyl group mentioned above is applicable to the alkyl group in an arylalkyl group and a thioalkyl group.

  In the present specification, the description regarding the heteroaryl group described above is applicable except that the heteroarylene group is a divalent group.

  In the present specification, the description regarding the aryl group described above is applicable except that the arylene group is a divalent group.

  In one embodiment of the present specification, X1 and X2 are all hydrogen.

  In another embodiment, X1 and X2 are directly bonded to each other to form a 5-membered ring.

  In one embodiment of the present specification, n1 and n2 are 0 or 1, and at least one of n1 and n2 is an integer of 1.

  According to another embodiment, n1 and n2 are integers of one.

  According to one embodiment of the present specification, Ar 1 is a substituted or unsubstituted hydrocarbon ring group having 3 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

  In another embodiment, Ar 1 is a substituted or unsubstituted hydrocarbon ring group having 3 to 40 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

前記構造において、
Ｌ２、Ｒ３およびＲ４の定義は、前記化学式１における定義と同じであり、
Ｒ'およびＲ"は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；アリールオキシ基；アルキルチオキシ基；アリールチオキシ基；アルキルスルホキシ基；アリールスルホキシ基；シリル基；ホウ素基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のアリール基；置換もしくは非置換のアルアルキル基；置換もしくは非置換のアルキルアミン基；置換もしくは非置換のアラルキルアミン基；置換もしくは非置換のヘテロアリールアミン基；置換もしくは非置換のアリールアミン基；置換もしくは非置換のアリールヘテロアリールアミン基；置換もしくは非置換のアリールホスフィン基；または置換もしくは非置換のヘテロ環基であり、
前記構造は、さらに置換されていてもよい。 In one embodiment of the present specification, the Ar1-L2-NR3R4 has one of the following structures.

In the structure,
The definitions of L2, R3, and R4 are the same as the definitions in Chemical Formula 1,
R ′ and R ″ are the same as or different from each other, and are independently hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkylsulfoxy group Arylsulfoxy group; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted Substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine group; substituted or unsubstituted arylheteroarylamine A group; a substituted or unsubstituted arylphosphine group; Other is a substituted or unsubstituted heterocyclic group,
The structure may be further substituted.

  In one embodiment of the present specification, R ′ and R ″ are the same or different from each other, and each independently represents hydrogen; deuterium; halogen group; silyl group; boron group; substituted or unsubstituted alkyl group; Unsubstituted or substituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine A group; a substituted or unsubstituted arylheteroarylamine group; or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, R ′ and R ″ are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; An unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, R ′ and R ″ are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; substituted or unsubstituted. A cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

  In one embodiment of the present specification, R ′ and R ″ are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

  In another embodiment, R ′ and R ″ are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

  According to another embodiment, the R ′ and R ″ are the same or different from each other, and each independently represents a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted tert- It is a butyl group.

  In another embodiment, R ′ and R ″ are the same or different from each other, and are each independently a methyl group, an ethyl group, or a tert-butyl group.

［化学式１−Ｂ］

［化学式１−Ｃ］

［化学式１−Ｄ］

［化学式１−Ｅ］

［化学式１−Ｆ］

前記化学式１−Ａ〜１−Ｆにおいて、
Ｘ１、Ｘ２、Ｒ１〜Ｒ８、Ｌ１、Ｌ２、ｎ１およびｎ２は、前記化学式１における定義と同じであり、
Ｗ１〜Ｗ６は、互いに同一または異なり、それぞれ独立に、Ｏ、Ｓ、ＳｉＴ１Ｔ２、またはＣＴ３Ｔ４であり、
Ｔ１〜Ｔ４、Ｒ１０１〜Ｒ１０６は、互いに同一または異なり、それぞれ独立に、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
ｓ１およびｓ３はそれぞれ、０〜５の整数であり、
ｓ２およびｓ４はそれぞれ、０〜７の整数であり、
ｓ５およびｓ６はそれぞれ、０〜４の整数であり、
ｓ１〜ｓ６がそれぞれ２以上の整数の場合、括弧内の置換基は、互いに同一または異なる。 According to one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 may be any one selected from the following Chemical Formulas 1-A to 1-F.
[Chemical Formula 1-A]

[Chemical Formula 1-B]

[Chemical Formula 1-C]

[Chemical Formula 1-D]

[Chemical Formula 1-E]

[Chemical Formula 1-F]

In the chemical formulas 1-A to 1-F,
X1, X2, R1 to R8, L1, L2, n1, and n2 are the same as defined in Chemical Formula 1,
W1 to W6 are the same or different from each other, and are each independently O, S, SiT1T2, or CT3T4,
T1-T4 and R101-R106 are the same as or different from each other, and each independently represents hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; Or an unsubstituted heteroaryl group,
s1 and s3 are each an integer of 0 to 5,
s2 and s4 are each an integer of 0 to 7,
s5 and s6 are each an integer of 0 to 4,
When s1 to s6 are each an integer of 2 or more, the substituents in parentheses are the same or different from each other.

  According to one embodiment of the present specification, the s1 is 0 or 1.

  According to one embodiment of the present specification, the s2 is 0 or 1.

  According to one embodiment of the present specification, the s3 is 0 or 1.

  According to one embodiment of the present specification, the s4 is 0 or 1.

  According to one embodiment of the present specification, the s5 is 0 or 1.

  According to one embodiment of the present specification, the s6 is 0 or 1.

  According to one embodiment of the present specification, the T1 to T4 are the same or different from each other, and are each independently hydrogen; or a substituted or unsubstituted alkyl group.

  In another embodiment, the T1 to T4 are the same or different from each other, and are each independently hydrogen; or a substituted or unsubstituted alkyl group.

  According to another embodiment, the T1 to T4 are the same or different from each other, and are each independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

  In another embodiment, T1 to T4 are the same as or different from each other, and are each independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

  According to another embodiment, the T1 to T4 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted t- It is a butyl group.

  In another embodiment, T1 to T4 are methyl groups.

  In one embodiment of the present specification, R101 to R106 are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

  According to another embodiment, the R101 to R106 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; or a substituted or unsubstituted carbon group having 6 to 6 carbon atoms. 60 aryl groups.

  In another embodiment, the R101 to R106 are the same or different from each other, and are independently hydrogen; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted carbon group having 6 to 30 carbon atoms. An aryl group.

  According to another embodiment, R101-R106 are hydrogen.

  In one embodiment of the present specification, R 5 to R 8 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; silyl group; boron group; substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, R 5 to R 8 are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted carbon number. A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

  In one embodiment of the present specification, R5 to R8 are the same or different from each other, and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon number. A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

  In another embodiment, R5 to R8 are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon atom having 6 to 6 carbon atoms. 30 aryl groups; or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

  According to another embodiment, R5 to R8 are the same or different from each other, and are independently hydrogen; deuterium; substituted or unsubstituted methyl group; substituted or unsubstituted ethyl group; substituted or unsubstituted a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted dibenzofuran group.

  In another embodiment, the R5 to R8 are the same or different from each other, and are independently hydrogen, deuterium, methyl group, ethyl group, tert-butyl group, phenyl group, biphenyl group, naphthylene group, or dibenzofuran group. It is.

  According to another embodiment, R5 and R8 are the same or different from each other and are each independently hydrogen or a tert-butyl group.

  In one embodiment of the present specification, L 1 and L 2 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted carbon number 2 It is a bivalent heterocyclic group of -30.

  In another embodiment, L1 and L2 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; Substituted or unsubstituted naphthalene group; substituted or unsubstituted fluorenylene group; substituted or unsubstituted phenanthrenylene group; substituted or unsubstituted anthracenylene group; substituted or unsubstituted triphenylenyl group; substituted or unsubstituted thiophenylene A substituted or unsubstituted furanylene group; a substituted or unsubstituted pyrrolene group; a substituted or unsubstituted dibenzofuranylene group; a substituted or unsubstituted dibenzothiophenylene group; or a substituted or unsubstituted carbazolylene group.

  According to another embodiment, the L1 and L2 are the same or different from each other, and each independently represents a phenylene group; a biphenylylene group; a terphenylene group; a naphthalene group; a 9,9-diphenylfluorenyl group; -Dimethylfluorenyl group; phenanthrylene group; anthracenylene group; triphenylenyl group; thiophenylene group; furanylene group; pyrrolene group substituted or unsubstituted by methyl group or phenyl group; dibenzofuranylene group; dibenzothiophenylene group; A carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a direct bond; or one of the following structures.

  In one embodiment of the present specification, L1 and L2 are direct bonds.

  In one embodiment of the present specification, R1 to R4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted carbon group having 2 to 60 carbon atoms. It is a heterocyclic group.

  In one embodiment of the present specification, R1 to R4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted carbon group having 2 to 40 carbon atoms. It is a heterocyclic group. According to another embodiment, R1 to R4 are the same or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; Substituted or unsubstituted anthracenyl group; substituted or unsubstituted phenanthryl group; substituted or unsubstituted triphenylenyl group; substituted or unsubstituted fluoranthenyl group; substituted or unsubstituted chrysenyl group; substituted Or substituted pyrenyl group; substituted or unsubstituted fluorenyl group; substituted or unsubstituted indenofluorenyl group; substituted or unsubstituted benzofluorenyl group; substituted or unsubstituted pyridyl group; substituted or unsubstituted A substituted or unsubstituted pyridazinyl group; A substituted or unsubstituted pyrimidinyl group; a substituted or unsubstituted quinolinyl group; a substituted or unsubstituted quinoxalinyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; substituted or unsubstituted naphthobenzothiophene group; substituted or unsubstituted benzofuran group; substituted or unsubstituted benzothiophene group; substituted or unsubstituted benzimidazole A substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted fluorenobenzofuran group; or a substituted or unsubstituted benzofuranodibenzofuran group.

前記構造において、
Ｒ２０１〜Ｒ２９７は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；シリル基；ホウ素基；置換もしくは非置換のアミン基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
ａ１、ａ６、ａ１０、ａ２３およびａ２５はそれぞれ、０〜５の整数であり、
ａ２、ａ５、ａ８、ａ９、ａ１４、ａ１６、ａ１７、ａ２１、ａ２８〜ａ３５、ｂ１〜ｂ４、ｂ６〜ｂ９、ｂ１１〜ｂ１３、ｂ１５およびｂ１７〜ｂ３２はそれぞれ、０〜４の整数であり、
ａ３およびａ２２はそれぞれ、０〜７の整数であり、
ａ４、ａ７、ａ１２、ａ１５、ａ１９、ａ２６およびａ２７はそれぞれ、０〜３の整数であり、
ａ１１は、０〜９の整数であり、
ａ１３、ａ２０およびａ２４はそれぞれ、０〜６の整数であり、
ａ１８、ｂ５、ｂ１０、ｂ１４およびｂ１６はそれぞれ、０〜２の整数であり、
ａ１８、ｂ５、ｂ１０、ｂ１４およびｂ１６が２の場合、括弧内の置換基は、互いに異なり、
ａ１、ａ６、ａ１０、ａ２３、ａ２５、ａ２、ａ５、ａ８、ａ９、ａ１４、ａ１６、ａ１７、ａ２１、ａ２８〜ａ３５、ｂ１〜ｂ４、ｂ６〜ｂ９、ｂ１１〜ｂ１３、ｂ１５、ｂ１７〜ｂ３２、ａ３、ａ２２、ａ４、ａ７、ａ１２、ａ１５、ａ１９、ａ２６、ａ２７、ａ１１、ａ１３、ａ２０およびａ２４がそれぞれ２以上の場合、括弧内の置換基は、互いに同一または異なる。 In one embodiment of the present specification, R1 to R4 may be the same or different from each other, and may each independently be any one selected from the structures described below.

In the structure,
R201 to R297 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; nitrile group; nitro group; silyl group; boron group; substituted or unsubstituted amine group; A substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
a1, a6, a10, a23 and a25 are each an integer of 0 to 5,
a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are each an integer of 0 to 4,
a3 and a22 are each an integer of 0 to 7,
a4, a7, a12, a15, a19, a26 and a27 are each an integer of 0 to 3,
a11 is an integer of 0 to 9,
a13, a20 and a24 are each an integer of 0 to 6,
a18, b5, b10, b14 and b16 are each an integer of 0 to 2,
when a18, b5, b10, b14 and b16 are 2, the substituents in parentheses are different from each other;
a1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28-a35, b1-b4, b6-b9, b11-b13, b15, b17-b32, a3, When a22, a4, a7, a12, a15, a19, a26, a27, a11, a13, a20 and a24 are each 2 or more, the substituents in parentheses are the same or different from each other.

  In one embodiment of the present specification, R201 to R297 are the same or different from each other, and each independently represents hydrogen; deuterium; a silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group.

  In another embodiment, R201 to R297 are the same as or different from each other, and each independently represents hydrogen; deuterium; a silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon. A cycloalkyl group having 3 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

  In another embodiment, R201 to R297 are the same as or different from each other, and each independently represents hydrogen; deuterium; a silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted carbon. A cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

  In another embodiment, R201 to R297 are the same as or different from each other, and each independently represents hydrogen; deuterium; a silyl group substituted or unsubstituted with an alkyl group; substituted or unsubstituted alkyl having 1 to 20 carbons; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

  According to another embodiment, R201 to R297 are the same or different from each other, and each independently represents hydrogen; deuterium; a silyl group substituted with a methyl group; a substituted or unsubstituted methyl group; substituted or unsubstituted. Substituted or unsubstituted propyl group; substituted or unsubstituted t-butyl group; substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted cyclopentyl group; or substituted or unsubstituted A substituted cyclohexyl group.

  In another embodiment, R201 to R297 are the same or different from each other, and are independently hydrogen, deuterium, trimethylsilyl group, methyl group, t-butyl group, phenyl group, biphenyl group, or naphthyl group.

  In one embodiment of the present specification, each of the a1 to a35 and b1 to b32 is an integer of 0 to 2.

Further, according to one embodiment of the specification, the heterocyclic compound of Formula 1 may be any one selected from the following compounds.

  The heterocyclic compound which concerns on one embodiment of this specification is manufactured with the manufacturing method mentioned later. For example, the heterocyclic compound of Formula 1 has a core structure as in the following production example. Substituents are attached by methods known in the art, and the type, position or number of substituents can be altered by techniques known in the art.

  According to an embodiment of the present specification, the first electrode, the second electrode, and one or more organic layers disposed between the first electrode and the second electrode, One or more layers of the above provide an organic light emitting device including the heterocyclic compound according to an embodiment of the present specification.

  According to one embodiment of the present specification, the organic layer of the organic light emitting device of the present specification may have a single layer structure, or may have a multilayer structure in which two or more organic layers are stacked. . For example, the organic light emitting device of the present invention has a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. Can do. However, the structure of the organic light emitting device is not limited to this, and may include a smaller or larger number of organic layers.

  The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

  FIG. 1 illustrates an organic light emitting device structure in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In this structure, the compound may be included in the light emitting layer 3.

  FIG. 2 illustrates an organic light emitting device structure in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked on a substrate 1. Has been. In this structure, the compound may be contained in the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, or the electron transport layer 7.

  According to an embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or an electron block layer, and the hole injection layer, the hole transport layer, or the electron block layer includes: The heterocyclic compound represented by Formula 1 is included.

  According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1.

前記化学式２において、
Ｒ９は、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；アリールオキシ基；アルキルチオキシ基；アリールチオキシ基；アルキルスルホキシ基；アリールスルホキシ基；シリル基；ホウ素基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のアリール基；置換もしくは非置換のアルアルキル基；置換もしくは非置換のアルキルアミン基；置換もしくは非置換のアラルキルアミン基；置換もしくは非置換のヘテロアリールアミン基；置換もしくは非置換のアリールアミン基；置換もしくは非置換のアリールヘテロアリールアミン基；置換もしくは非置換のアリールホスフィン基；または置換もしくは非置換のヘテロ環基であり、
ｐは、０〜６の整数であり、
ｐが２以上の場合、括弧内の置換基は、互いに同一または異なり、
Ｌ３〜Ｌ６は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換のアリーレン基；または置換もしくは非置換のヘテロアリーレン基であり、
Ａｒ２〜Ａｒ５は、互いに同一または異なり、それぞれ独立に、水素；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基である。 According to an embodiment of the present specification, the organic layer includes a light emitting layer, the organic layer includes a heterocyclic compound represented by the chemical formula 1, and the light emitting layer is represented by the following chemical formula 2. A further compound.
[Chemical formula 2]

In Formula 2,
R9 represents hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, arylsulfoxy group, silyl group, boron group, substituted Or a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; a substituted or unsubstituted arylphosphine group; Or an unsubstituted heterocyclic group,
p is an integer of 0-6,
when p is 2 or more, the substituents in parentheses are the same or different from each other;
L3 to L6 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
Ar2 to Ar5 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

  According to one embodiment of the present specification, R9 is hydrogen; deuterium; halogen group; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted. Substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine group; substituted or unsubstituted arylheteroarylamine Group; or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, the R9s are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Group; or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, the R9s are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

  In one embodiment of the present specification, the R9s are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

  According to another embodiment, R9 is hydrogen.

  In one embodiment of the present specification, p is 0 or 1.

  In one embodiment of the present specification, L 3 to L 6 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted carbon number 2 ˜60 heteroarylene groups.

  In one embodiment of the present specification, the L3 to L6 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted carbon number 2 ˜40 heteroarylene groups.

  According to another embodiment, the L3 to L6 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted terphenylene. Substituted or unsubstituted naphthylene group; substituted or unsubstituted anthracenylene group; substituted or unsubstituted phenanthrylene group; substituted or unsubstituted triphenylene group; substituted or unsubstituted fluorenyl group; substituted or unsubstituted A substituted or unsubstituted furanylene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted dibenzofuranylene group; or a substituted or unsubstituted carbazolylene group.

  In another embodiment, L3 to L6 are the same or different from each other, and are each independently a direct bond; phenylene group; biphenylylene group; terphenylene group; naphthylene group; anthracenylene group; phenanthrylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; a thiophenylene group; a furanylene group; a dibenzothiophenylene group; a dibenzofuranylene group; or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to another embodiment, the L3 to L6 may be the same or different from each other, and each independently may be directly bonded; or may be selected from the following structures:

  According to one embodiment of the present specification, L3 is a direct bond.

  According to one embodiment of the present specification, L4 is a phenylene group.

  According to one embodiment of the present specification, L5 and L6 are direct bonds.

  In one embodiment of the present specification, Ar 2 to Ar 5 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted carbon group having 2 to 60 carbon atoms. A heteroaryl group;

  According to another embodiment, Ar2 to Ar5 are the same or different from each other, and each independently represents hydrogen; an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms; An aryl group having 6 to 60 carbon atoms; or an aryl group having 2 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms substituted or unsubstituted with an aryl group having 2 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.

  In another embodiment, Ar 2 to Ar 5 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Unsubstituted or substituted phenanthrene group; substituted or unsubstituted anthracene group; substituted or unsubstituted triphenylene group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted naphthobenzofuran group; substituted or unsubstituted dibenzothiophene group; Unsubstituted or substituted carbazole group; substituted or unsubstituted fluorene group; substituted or unsubstituted thiophene group; substituted or unsubstituted furan group; substituted or unsubstituted benzothiophene group; substituted or unsubstituted benzofuran group; Substituted benzoca Substituted or unsubstituted benzofluorene group; substituted or unsubstituted indolecarbazole group; substituted or unsubstituted pyridyl group; substituted or unsubstituted isoquinolyl group; substituted or unsubstituted quinolyl group; substituted or unsubstituted A quinazolyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted dihydroacridine group; A substituted xanthene group; or a substituted or unsubstituted dibenzosilole group.

  According to another embodiment, Ar 2 to Ar 5 are the same or different from each other, and are independently hydrogen; phenyl group; biphenyl group; naphthyl group substituted or unsubstituted by aryl group; phenanthrene group; anthracene group; An aryl group substituted or unsubstituted dibenzofuran group; a naphthobenzofuran group; an aryl group substituted or unsubstituted dibenzothiophene group; an alkyl group or an aryl group substituted or unsubstituted carbazole group; an alkyl group or an aryl group Substituted or unsubstituted fluorene group; substituted or unsubstituted thiophene group with aryl group; substituted or unsubstituted furan group with aryl group; benzothiophene group; benzofuran group; substituted or unsubstituted with alkyl group or aryl group Benzocarbazole An benzofluorene group substituted or unsubstituted with an alkyl group or an aryl group; an indolecarbazole group; a pyridyl group; an isoquinolyl group substituted or unsubstituted with an aryl group; a quinolyl group; a quinazolyl group substituted or unsubstituted with an aryl group; Substituted or unsubstituted triazine group with an aryl group; substituted or unsubstituted benzimidazole group with an aryl group; a benzoxazole group substituted or unsubstituted with an aryl group; a benzothiazole group substituted or unsubstituted with an aryl group; an alkyl group, or A dihydroacridine group substituted or unsubstituted with an aryl group; an alkyl group or a xanthene group substituted or unsubstituted with an aryl group; or a dibenzosilole group substituted or unsubstituted with an alkyl group or an aryl group.

  In another embodiment, Ar2 to Ar5 are the same or different from each other, and are independently hydrogen; phenyl group; biphenyl group; naphthyl group substituted or unsubstituted with phenyl group; phenanthrene group; anthracene group; Dibenzofuran group substituted or unsubstituted by phenyl group; naphthobenzofuran group; dibenzothiophene group substituted or unsubstituted by phenyl group; carbazole group substituted or unsubstituted by methyl group, ethyl group, or phenyl group; methyl group, or phenyl Substituted or unsubstituted fluorene group; phenyl group substituted or unsubstituted thiophene group; phenyl group substituted or unsubstituted furan group; benzothiophene group; benzofuran group; methyl group or phenyl group substituted or unsubstituted Benzocarbazo Benzofluorene group substituted or unsubstituted by methyl group or phenyl group; indolecarbazole group; pyridyl group substituted or unsubstituted by phenyl group or naphthyl group; isoquinolyl group substituted or unsubstituted by phenyl group; quinolyl group Substituted or unsubstituted quinazolyl group with phenyl group; substituted or unsubstituted triazine group with phenyl group; benzimidazole group substituted or unsubstituted with phenyl group; benzoxazole group substituted or unsubstituted with phenyl group; A substituted or unsubstituted benzothiazole group; a methyl group or a phenyl group substituted or unsubstituted dihydroacridine group; a methyl group or phenyl group substituted or unsubstituted xanthene group; or a methyl group or phenyl group substituted or Unsubstituted diben It is a silole group.

In one embodiment of the present specification, Ar 2 to Ar 5 may be the same or different from each other, and may be independently selected from hydrogen;

前記化学式３において、
Ｒ１０は、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；アリールオキシ基；アルキルチオキシ基；アリールチオキシ基；アルキルスルホキシ基；アリールスルホキシ基；シリル基；ホウ素基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアルケニル基；置換もしくは非置換のアリール基；置換もしくは非置換のアルアルキル基；置換もしくは非置換のアルキルアミン基；置換もしくは非置換のアラルキルアミン基；置換もしくは非置換のヘテロアリールアミン基；置換もしくは非置換のアリールアミン基；置換もしくは非置換のアリールヘテロアリールアミン基；置換もしくは非置換のアリールホスフィン基；または置換もしくは非置換のヘテロ環基であり、
ｑは、０〜７の整数であり、
ｑが２以上の場合、括弧内の置換基は、互いに同一または異なり、
Ｌ７〜Ｌ９は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換のアリーレン基；または置換もしくは非置換のヘテロアリーレン基であり、
Ａｒ６〜Ａｒ８は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基である。 According to an embodiment of the present specification, the organic layer includes a light emitting layer, the organic layer includes a heterocyclic compound represented by the chemical formula 1, and the light emitting layer is represented by the following chemical formula 3. A further compound.
[Chemical formula 3]

In Formula 3,
R10 represents hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, arylsulfoxy group, silyl group, boron group, substituted Or a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; a substituted or unsubstituted arylphosphine group; Or an unsubstituted heterocyclic group,
q is an integer of 0 to 7,
when q is 2 or more, the substituents in parentheses are the same or different from each other;
L7 to L9 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar6 to Ar8 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

  In one embodiment of the present specification, R10 represents hydrogen; deuterium; halogen group; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl. A substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, the R10s are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Group; or a substituted or unsubstituted heterocyclic group.

  In one embodiment of the present specification, the R10s are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

  In one embodiment of the present specification, the R10s are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

  In another embodiment, R10 is hydrogen.

  In one embodiment of the present specification, q is 0 or 1.

  In one embodiment of the present specification, L7 to L9 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted carbon number 2 ˜60 heteroarylene groups.

  In one embodiment of the present specification, L7 to L9 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted carbon number of 2 ˜40 heteroarylene groups.

  According to another embodiment, L7 to L9 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted terphenylene. Substituted or unsubstituted naphthylene group; substituted or unsubstituted anthracenylene group; substituted or unsubstituted phenanthrylene group; substituted or unsubstituted triphenylene group; substituted or unsubstituted fluorenyl group; substituted or unsubstituted A substituted or unsubstituted furanylene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted dibenzofuranylene group; or a substituted or unsubstituted carbazolylene group.

  In another embodiment, L7 to L9 are the same or different from each other, and are each independently a direct bond; a phenylene group; a biphenylylene group; a terphenylene group; a naphthylene group; an anthracenylene group; a phenanthrylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; a thiophenylene group; a furanylene group; a dibenzothiophenylene group; a dibenzofuranylene group; or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to another embodiment, the L7 to L9 may be the same or different from each other, and may be independently selected from a direct bond;

  In one embodiment of the present specification, L7 to L9 are direct bonds.

  In one embodiment of the present specification, Ar 6 to Ar 8 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted carbon group having 2 to 60 carbon atoms; A heteroaryl group;

  According to another embodiment, Ar6 to Ar8 are the same or different from each other, and each independently represents an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms, which is substituted or unsubstituted. An aryl group having 6 to 60 carbon atoms; or a heteroaryl group having 2 to 60 carbon atoms which is substituted or unsubstituted with an aryl group having 1 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.

  In another embodiment, Ar6 to Ar8 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted Substituted or unsubstituted anthracene group; substituted or unsubstituted triphenylene group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted naphthobenzofuran group; substituted or unsubstituted dibenzothiophene group; substituted or unsubstituted Substituted or unsubstituted fluorene group; substituted or unsubstituted thiophene group; substituted or unsubstituted furan group; substituted or unsubstituted benzothiophene group; substituted or unsubstituted benzofuran group; substituted or unsubstituted Benzocarbazo Substituted or unsubstituted benzofluorene group; substituted or unsubstituted indolecarbazole group; substituted or unsubstituted pyridyl group; substituted or unsubstituted isoquinolyl group; substituted or unsubstituted quinolyl group; substituted or unsubstituted A quinazolyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted dihydroacridine group; A substituted xanthene group; or a substituted or unsubstituted dibenzosilole group.

  According to another embodiment, the Ar6 to Ar8 are the same or different from each other, and each independently represents a phenyl group; a biphenyl group; an aryl group-substituted or unsubstituted naphthyl group; a phenanthrene group; an anthracene group; Dibenzofuran group substituted or unsubstituted by aryl group; naphthobenzofuran group; dibenzothiophene group substituted or unsubstituted by aryl group; alkyl group or carbazole group substituted or unsubstituted by aryl group; substituted by alkyl group or aryl group Or an unsubstituted fluorene group; an aryl group substituted or unsubstituted thiophene group; an aryl group substituted or unsubstituted furan group; a benzothiophene group; a benzofuran group; an alkyl group or an aryl group substituted or unsubstituted benzocarbazole Group; Indolecarbazole group; pyridyl group; isoquinolyl group substituted or unsubstituted with aryl group; quinolyl group; quinazolyl group substituted or unsubstituted with aryl group; aryl group Substituted or unsubstituted triazine group; aryl group substituted or unsubstituted benzimidazole group; aryl group substituted or unsubstituted benzoxazole group; aryl group substituted or unsubstituted benzothiazole group; alkyl group or aryl A dihydroacridine group substituted or unsubstituted by a group; a xanthene group substituted or unsubstituted by an alkyl group or an aryl group; or a dibenzosilole group substituted or unsubstituted by an alkyl group or an aryl group.

  In another embodiment, the Ar6 to Ar8 are the same or different from each other, and each independently represents a phenyl group; a biphenyl group; a naphthyl group substituted or unsubstituted with a phenyl group; a phenanthrene group; an anthracene group; a triphenylene group; Substituted or unsubstituted dibenzofuran group; naphthobenzofuran group; phenyl group substituted or unsubstituted dibenzothiophene group; methyl group, ethyl group, or phenyl group substituted or unsubstituted carbazole group; methyl group or phenyl group A substituted or unsubstituted fluorene group; a phenyl group substituted or unsubstituted thiophene group; a phenyl group substituted or unsubstituted furan group; a benzothiophene group; a benzofuran group; a methyl group or a phenyl group substituted or unsubstituted benzone Carbazole group Benzofluorene group substituted or unsubstituted by methyl group or phenyl group; indolecarbazole group; pyridyl group substituted or unsubstituted by phenyl group or naphthyl group; isoquinolyl group substituted or unsubstituted by phenyl group; quinolyl group; phenyl group A substituted or unsubstituted quinazolyl group; a phenyl group substituted or unsubstituted triazine group; a phenyl group substituted or unsubstituted benzimidazole group; a phenyl group substituted or unsubstituted benzoxazole group; a phenyl group substituted or unsubstituted Substituted benzothiazole group; Dihydroacridine group substituted or unsubstituted by methyl group or phenyl group; Xanthene group substituted or unsubstituted by methyl group or phenyl group; or Substituted or unsubstituted by methyl group or phenyl group Dibenzoshiro A Le group.

In one embodiment of the present specification, Ar6 to Ar8 may be the same or different from each other, and may be independently selected from the following structures.

  In one embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a host of the light emitting layer.

  According to an embodiment of the present specification, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer.

  According to an embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by the chemical formula 1 as a dopant of the light emitting layer, and the chemical formula 2 or the chemical formula 3 The compound represented by these is included as a host of a light emitting layer.

  According to an embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by the chemical formula 1 as a dopant of the light emitting layer, and the chemical formula 2 or the chemical formula 3 The compound represented by formula (1) can be included as a host of the light emitting layer, and the heterocyclic compound represented by Formula 1 can be doped by 2 to 10 wt%.

  According to an embodiment of the present specification, the organic material layer includes a hole blocking layer, an electron transporting layer, or an electron injection layer, and the hole blocking layer, the electron transporting layer, or the electron injection layer has the chemical formula. The heterocyclic compound represented by 1 is included.

  According to an embodiment of the present specification, the organic material layer further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. But you can.

  An organic light emitting device according to an embodiment of the present specification includes a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, The heterocyclic compound represented by Formula 1 is included.

  According to another embodiment, the organic light emitting device of the present invention includes a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, and the light emitting device. The layer may include the heterocyclic compound represented by Formula 1 as a dopant, and may further include a host.

  In another embodiment, the organic light emitting device of the present invention includes a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, The heterocyclic compound represented by Chemical Formula 1 may be included as a dopant and may further include a host, or the host may be a compound represented by Chemical Formula 2 or 3. In addition to the light emitting layer, the organic light emitting device may further include one or more organic material layers selected from a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer. However, the structure of the organic light emitting device is not limited to this.

  According to another embodiment, the organic light emitting device of the present invention includes a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode. One or more organic material layers selected from a hole injection layer and a hole transport layer may be included between the electrode and the light emitting layer, and an electron transport layer and an electron are interposed between the second electrode and the light emitting layer. One or more organic layers selected from among the injection layers may be included. However, the structure of the organic light emitting device of the present invention is not limited thereto.

  In another embodiment, the organic light emitting device of the present invention includes a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, the light emitting layer comprising: The heterocyclic compound represented by Chemical Formula 1 is included as a host, and one or more organic layers selected from a hole injection layer and a hole transport layer are included between the first electrode and the light emitting layer. One or more organic material layers selected from an electron transport layer and an electron injection layer may be included between the second electrode and the light emitting layer. However, the structure of the organic light emitting device of the present invention is not limited thereto.

  According to another embodiment, the organic light emitting device of the present invention includes a first electrode, a second electrode, and a light emitting layer provided between the first electrode and the second electrode, and the light emitting layer. Includes a heterocyclic compound represented by Chemical Formula 1 as a dopant, a compound represented by Chemical Formula 2 or 3 as a host of a light emitting layer, and a hole injection layer between the first electrode and the light emitting layer. And at least one organic material layer selected from the hole transport layer, and at least one organic material selected from the electron transport layer and the electron injection layer between the second electrode and the light emitting layer. Layers can be included. However, the structure of the organic light emitting device of the present invention is not limited thereto.

  The organic light emitting device of the present specification is an organic light emitting device in the art except that one or more of the organic layers includes the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by Formula 1. Manufactured with known materials and methods.

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

  For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation (PVD), a metal or conductive metal oxide on the substrate, Alternatively, these alloys are vapor-deposited to form a first electrode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a second electrode is formed thereon. It is manufactured by vapor-depositing a material that can be used as In addition to this method, an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a first electrode material from a second electrode material on a substrate. In addition, the heterocyclic compound represented by the chemical formula 1 is formed on the organic layer not only by a vacuum deposition method but also by a solution coating method at the time of manufacturing the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, ink jet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

  According to one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

  According to another embodiment of the present specification, the first electrode is a cathode and the second electrode is an anode.

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

In general, the cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF / Al or LiO ₂ / There are materials having a multilayer structure such as Al and Mg / Ag, but are not limited thereto.

  The hole injection layer is a layer for injecting holes from an electrode. As a hole injection material, it has the ability to transport holes, and the hole injection effect from the anode, the light emitting layer or the light emitting material A compound that has an excellent hole injection effect, prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and has an excellent thin film forming ability is preferable. Preferably, the hole injection material HOMO (high occluded molecular orbital) is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine organic material, hexanitrile hexaazatriphenylene organic material, quinacridone organic material, perylene organic material, Examples include, but are not limited to, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

  The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As the hole transport material, the light emitting layer receives hole transport from the anode or the hole injection layer. A substance that can be transferred to the group and has a high mobility for holes is preferable. Specific examples include, but are not limited to, arylamine organic materials, conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion.

The light-emitting substance of the light-emitting layer is a substance that can emit light in the visible light region by receiving and combining holes and electron transport from the hole transport layer and the electron transport layer, respectively, and has a quantum efficiency for fluorescence and phosphorescence A good material is preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole and benz Examples include, but are not limited to, imidazole compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, and the like.

  The light emitting layer may include a host material and a dopant material. Examples of the host material include a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan. Examples include, but are not limited to, compounds and pyrimidine derivatives.

  Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes an arylamino group such as pyrene, anthracene, chrysene, perifuranthene, and a styrylamine compound. Is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group The substituent to be substituted is substituted or unsubstituted. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material that can be well received by the electron injection from the cathode and transferred to the light emitting layer, and A substance with high mobility is preferred. Specific examples include 8-hydroxyquinoline Al complex; complexes including Alq _3; organic radical compounds; hydroxy flavone - there are metal complexes, but are not limited to only these. The electron transport layer can be used with any desired cathode material, as used by the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

  The electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, and has an excellent electron injection effect for a light emitting layer or a light emitting material. It is preferable to use a compound that prevents the exciton generated in step 1 from moving to the hole injection layer and has an excellent thin film forming ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone and their derivatives, metal complex compounds, And nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

  Examples of the metal complex compound include 8-hydroxyquinolinatolithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, and tris (8-hydroxyquino). Linato) 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-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum Bis (2-methyl-8-quinolinato) (2-naphth Acrylate), and the like gallium, but are not limited to these.

  The organic light emitting device according to the present specification may be a front light emitting type, a rear light emitting type, or a double side light emitting type depending on a material to be used.

  Hereinafter, the present specification will be described in detail by way of examples in order to specifically describe the present specification. However, the examples according to the present specification can be modified into various different forms, and the scope of the present specification is not construed to be limited to the examples described below. The examples herein are provided to provide a more thorough explanation of the specification to those having average knowledge in the art.

  <Synthesis example>

窒素雰囲気下、１Ｌフラスコに、２−ブロモ−５−クロロベンズアルデヒド（３０．０ｇ、１３７ｍｍｏｌ）、４−ジベンゾフラニルボロン酸（３１．９ｇ、１５０ｍｍｏｌ）をテトラヒドロフラン３７５ｍＬに完全に溶かした後、炭酸カリウム（５６．７ｇ、４１０ｍｍｏｌ）水溶液１２５ｍＬを添加し、テトラキス−（トリフェニルホスフィン）パラジウム（３．１６ｇ、２．７３ｍｍｏｌ）を添加した後、２４時間還流して撹拌した。反応完了後、常温に温度を下げてから、水とエチルアセテートで抽出して有機層を分離した。有機層は無水硫酸マグネシウムで処理後、濾過減圧濃縮した。固体はエチルアセテートで再結晶して、＜中間体１−１＞（３２．３ｇ、収率７７％）を得た。 Synthesis Example 1 Synthesis of Intermediate 1-1 Intermediate 1-1 was synthesized according to the following reaction formula.

Under a nitrogen atmosphere, 2-bromo-5-chlorobenzaldehyde (30.0 g, 137 mmol) and 4-dibenzofuranylboronic acid (31.9 g, 150 mmol) were completely dissolved in 375 mL of tetrahydrofuran in a 1 L flask, and then potassium carbonate. 125 mL of an aqueous solution (56.7 g, 410 mmol) was added, tetrakis- (triphenylphosphine) palladium (3.16 g, 2.73 mmol) was added, and the mixture was refluxed and stirred for 24 hours. After the completion of the reaction, the temperature was lowered to room temperature, followed by extraction with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate to obtain <Intermediate 1-1> (32.3 g, yield 77%).

  Mass [M + 1] = 307

１Ｌフラスコに、＜中間体１−１＞（３２．０ｇ、１０４ｍｍｏｌ）をテトラヒドロフラン４５０ｍＬに溶かした後、亜塩素酸ナトリウム（１４．２ｇ、１１５ｍｍｏｌ）、スルファミン酸（２０．３ｇ、２０９ｍｍｏｌ）を水（各７５ｍＬ）で希釈して添加し、４時間加熱撹拌した。反応完了後、常温に温度を下げてから、水とエチルアセテートで抽出して有機層を分離した。有機層は無水硫酸マグネシウムで処理後、濾過減圧濃縮した。固体はエチルアセテートとノルマルヘキサンで再結晶して、＜中間体１−２＞（２８．３ｇ、収率８４％）を得た。 Synthesis Example 2 Synthesis of Intermediate 1-2 Intermediate 1-2 was synthesized according to the following reaction formula.

In a 1 L flask, <Intermediate 1-1> (32.0 g, 104 mmol) was dissolved in 450 mL of tetrahydrofuran, and then sodium chlorite (14.2 g, 115 mmol) and sulfamic acid (20.3 g, 209 mmol) were added to water ( Diluted with 75 mL each) and added with stirring for 4 hours. After the completion of the reaction, the temperature was lowered to room temperature, followed by extraction with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and normal hexane to obtain <Intermediate 1-2> (28.3 g, yield 84%).

  Confirmed by TLC and HPLC

０．５Ｌフラスコに、＜中間体１−２＞（２８ｇ、８６．８ｍｍｏｌ）、メタンスルホン酸３５０ｍＬを入れて、８０℃で９時間加熱撹拌した。反応完了後、常温に温度を下げてから、水にゆっくり滴加して固体を生成した。生成された固体は水とエタノールで洗って、＜中間体１−３＞（２４．３ｇ、収率９２％）を得た。 Synthesis Example 3 Synthesis of Intermediate 1-3 Intermediate 1-3 was synthesized according to the following reaction formula.

<Intermediate 1-2> (28 g, 86.8 mmol) and 350 mL of methanesulfonic acid were placed in a 0.5 L flask, and the mixture was heated and stirred at 80 ° C. for 9 hours. After the reaction was completed, the temperature was lowered to room temperature and then slowly added dropwise to water to form a solid. The produced solid was washed with water and ethanol to obtain <Intermediate 1-3> (24.3 g, yield 92%).

  Mass [M + 1] = 305

窒素雰囲気下、０．５Ｌフラスコに、＜中間体１−３＞（９．５０ｇ、３１．２ｍｍｏｌ）をジクロロメタン３００ｍＬに入れて撹拌した後、ジクロロメタン５０ｍＬに希釈したブロミン９．９７ｇ（６２．３ｍｍｏｌ）をゆっくり滴加した後、４８時間常温で撹拌した。この後、生成された個体は濾過後、ジクロロメタンおよびノルマルヘキサンで洗った。固体はトルエンとノルマルヘキサンで再結晶して、＜中間体１−４＞（７．０ｇ、収率５９％）を得た。 Synthesis Example 4 Synthesis of Intermediate 1-4 Intermediate 1-4 was synthesized according to the following reaction formula.

In a 0.5 L flask, <Intermediate 1-3> (9.50 g, 31.2 mmol) was placed in 300 mL of dichloromethane and stirred in a 0.5 L flask, and then 9.97 g (62.3 mmol) of bromine diluted in 50 mL of dichloromethane. Was slowly added dropwise, followed by stirring at room temperature for 48 hours. Thereafter, the produced solid was filtered and washed with dichloromethane and normal hexane. The solid was recrystallized from toluene and normal hexane to obtain <Intermediate 1-4> (7.0 g, yield 59%).

  Mass [M + 1] = 383

窒素雰囲気下、０．５Ｌフラスコに、９−（２−ブロモフェニル）−９Ｈ−カルバゾール（７．５３ｇ、２３．４ｍｍｏｌ）とテトラヒドロフラン１８０ｍＬを入れて、−７８℃に冷却した。冷却された反応溶液にノルマルブチルリチウム（１０．８ｍＬ、２７．０ｍｍｏｌ）を滴加した後、１時間撹拌した。この後、＜中間体１−４＞を入れて、常温で撹拌した。反応完了後、飽和炭酸水素ナトリウムを入れて反応を終結した後、エチルアセテートと水で抽出した。有機層は無水硫酸マグネシウムで処理後、濾過減圧濃縮した。固体はエチルアセテートとノルマルヘキサンで再結晶して、＜中間体１−５＞（７．６０ｇ、収率６７％）を得た。 Synthesis Example 5 Synthesis of Intermediate 1-5 Intermediate 1-5 was synthesized according to the following reaction formula.

Under a nitrogen atmosphere, 9- (2-bromophenyl) -9H-carbazole (7.53 g, 23.4 mmol) and 180 mL of tetrahydrofuran were placed in a 0.5 L flask and cooled to -78 ° C. Normal butyl lithium (10.8 mL, 27.0 mmol) was added dropwise to the cooled reaction solution, followed by stirring for 1 hour. Thereafter, <Intermediate 1-4> was added and stirred at room temperature. After completion of the reaction, saturated sodium hydrogen carbonate was added to terminate the reaction, followed by extraction with ethyl acetate and water. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and normal hexane to obtain <Intermediate 1-5> (7.60 g, yield 67%).

  Mass [M + 1] = 626

０．２５Ｌフラスコに、＜中間体１−５＞（７．６０ｇ、１２．１ｍｍｏｌ）と酢酸（１００ｍＬ）、硫酸２滴を入れて、３時間加熱撹拌した。反応完了後、固体を濾過後、水とエタノールで洗った後、エチルアセテートとノルマルヘキサンで再結晶して、＜中間体１−６＞（７．０４ｇ、収率９５％）を得た。 Synthesis Example 6 Synthesis of Intermediate 1-6 Intermediate 1-6 was synthesized according to the following reaction formula.

<Intermediate 1-5> (7.60 g, 12.1 mmol), acetic acid (100 mL) and 2 drops of sulfuric acid were placed in a 0.25 L flask, and the mixture was heated and stirred for 3 hours. After completion of the reaction, the solid was filtered, washed with water and ethanol, and recrystallized with ethyl acetate and normal hexane to obtain <Intermediate 1-6> (7.04 g, yield 95%).

  Mass [M + 1] = 608

窒素雰囲気下、１Ｌフラスコに、２−（４−ブロモフェニル）ナフタレン（２３．０ｇ、０．０８１ｍｏｌ）、４−ｔブチルアニリン（１３．３ｇ、０．０８９ｍｏｌ）、ソジウムタートブトキシド（２３．４ｇ、０．２４４ｍｏｌ）、ビス（トリ−タート−ブチルホスフィン）パラジウム（０）（１．２５ｇ、２．４４ｍｍｏｌ）をトルエン３５０ｍＬに入れて、還流して撹拌した。反応が終わると、常温に冷やした後、トルエンと水で抽出して水層を除去した。無水硫酸マグネシウムで処理後、濾過減圧濃縮した。生成物はカラムクロマトグラフィー法で分離精製した後、トルエンとノルマルヘキサンで再結晶して、＜中間体２−１＞（１５．２ｇ、収率５３％）を得た。 Synthesis Example 7 Synthesis of Intermediate 2-1 Intermediate 2-1 was synthesized according to the following reaction formula.

In a 1 L flask under a nitrogen atmosphere, 2- (4-bromophenyl) naphthalene (23.0 g, 0.081 mol), 4-tbutylaniline (13.3 g, 0.089 mol), sodium tertbutoxide (23.4 g) 0.244 mol), bis (tri-tert-butylphosphine) palladium (0) (1.25 g, 2.44 mmol) was added to 350 mL of toluene, and the mixture was refluxed and stirred. When the reaction was completed, the mixture was cooled to room temperature and extracted with toluene and water to remove the aqueous layer. After treatment with anhydrous magnesium sulfate, the filtrate was concentrated under reduced pressure. The product was separated and purified by column chromatography and then recrystallized from toluene and normal hexane to obtain <Intermediate 2-1> (15.2 g, 53% yield).

  Mass [M + 1] = 352

窒素雰囲気下、０．２５Ｌフラスコに、＜中間体１−６＞（５．０ｇ、８．２１ｍｍｏｌ）、＜中間体１−７＞（６．３６ｇ、１８．１ｍｍｏｌ）、ソジウムｔブトキシド（３．９ｇ、４１ｍｍｏｌ）、ビス（トリｔブチルホスフィン）パラジウム（０）（２１０ｍｇ、０．４１ｍｍｏｌ）をトルエン８０ｍＬに入れて、還流して撹拌した。反応が終わると、常温に冷やした後、トルエンと水で抽出して水層を除去した。無水硫酸マグネシウムで処理後、濾過減圧濃縮した。生成物はカラムクロマトグラフィー法で分離精製した後、トルエンとノルマルヘキサンで再結晶して、化合物１（４．３ｇ、収率４３％）を得た。前記化合物１のＮＭＲ ｄａｔａを下記図３に示した。 Synthesis Example 8 Synthesis of Compound 1 Compound 1 was synthesized according to the following reaction formula.

In a 0.25 L flask under a nitrogen atmosphere, <Intermediate 1-6> (5.0 g, 8.21 mmol), <Intermediate 1-7> (6.36 g, 18.1 mmol), sodium t-butoxide (3. 9 g, 41 mmol), bis (tri-t-butylphosphine) palladium (0) (210 mg, 0.41 mmol) was placed in 80 mL of toluene and stirred at reflux. When the reaction was completed, the mixture was cooled to room temperature and extracted with toluene and water to remove the aqueous layer. After treatment with anhydrous magnesium sulfate, the filtrate was concentrated under reduced pressure. The product was separated and purified by column chromatography and then recrystallized from toluene and normal hexane to obtain Compound 1 (4.3 g, yield 43%). The NMR data of Compound 1 is shown in FIG.

  Mass [M + 1] = 1195

＜中間体１−４＞を用いて前記合成例５と同様に実験して、＜中間体３−１＞を合成した。 Synthesis Example 9 Synthesis of Intermediate 3-1 Intermediate 3-1 was synthesized according to the following reaction formula.

<Intermediate 1-4> was used in the same manner as in Synthesis Example 5 to synthesize <Intermediate 3-1>.

  Mass [M + 1] = 628

＜中間体３−１＞を用いて前記合成例６と同様に実験して、＜中間体３−２＞を合成した。 Synthesis Example 10 Synthesis of Intermediate 3-2 Intermediate 3-2 was synthesized according to the following reaction formula.

<Intermediate 3-1> was used in the same manner as in Synthesis Example 6 to synthesize <Intermediate 3-2>.

  Mass [M + 1] = 610

４−ｔブチルアニリンと４−ｔブチルブロモベンゼンを用いて前記合成例７と同様に実施して、＜中間体２−２＞を合成した。 Synthesis Example 11 Synthesis of Intermediate 2-2 Intermediate 2-2 was synthesized according to the following reaction formula.

<Intermediate 2-2> was synthesized in the same manner as in Synthesis Example 7 using 4-tbutylaniline and 4-tbutylbromobenzene.

  Mass [M + 1] = 282

＜中間体３−２＞と＜中間体２−２＞を用いて合成例８により化合物２を合成した。前記化合物２のＮＭＲ ｄａｔａを下記図３に示した。 Synthesis Example 12 Synthesis of Compound 2 Compound 2 was synthesized according to the following reaction formula.

Compound 2 was synthesized according to Synthesis Example 8 using <Intermediate 3-2> and <Intermediate 2-2>. The NMR data of Compound 2 is shown in FIG.

  Mass [M + 1] = 1057

４−ｔブチルアニリンと４−ｔブチルブロモベンゼンを用いて前記合成例７と同様に実施して、＜中間体２−３＞を合成した。 Synthesis Example 13: Synthesis of Intermediate 2-3 Intermediate 2-3 was synthesized according to the following reaction formula.

<Intermediate 2-3> was synthesized in the same manner as in Synthesis Example 7 using 4-tbutylaniline and 4-tbutylbromobenzene.

  Mass [M + 1] = 316

＜中間体１−６＞と＜中間体２−３＞を用いて合成例８により化合物３を合成した。 Synthesis Example 14 Synthesis of Compound 3 Compound 3 was synthesized according to the following reaction formula.

Compound 3 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-3>.

  Mass [M + 1] = 1123

４−ｔブチルアニリンと３−ブロモナフト｛２，３−ｂ｝ベンゾフランを用いて前記合成例７と同様に実施して、＜中間体２−４＞を合成した。 Synthesis Example 15 Synthesis of Intermediate 2-4 Intermediate 2-4 was synthesized according to the following reaction formula.

<Intermediate 2-4> was synthesized in the same manner as in Synthesis Example 7 using 4-tbutylaniline and 3-bromonaphtho {2,3-b} benzofuran.

  Mass [M + 1] = 366

＜中間体１−６＞と＜中間体２−４＞を用いて合成例８により化合物８を合成した。 Synthesis Example 16 Synthesis of Compound 8 Compound 8 was synthesized according to the following reaction formula.

Compound 8 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-4>.

  Mass [M + 1] = 1223

２−ブロモ−９，９−ジメチル−９Ｈ−フルオレンと９，９−ジメチル−９Ｈ−フルオレン−２−アミンを用いて前記合成例７と同様に実施して、＜中間体２−５＞を合成した。 Synthesis Example 17 Synthesis of Intermediate 2-5 Intermediate 2-5 was synthesized according to the following reaction formula.

<Intermediate 2-5> was synthesized in the same manner as in Synthesis Example 7 using 2-bromo-9,9-dimethyl-9H-fluorene and 9,9-dimethyl-9H-fluoren-2-amine. did.

  Mass [M + 1] = 366

＜中間体１−６＞と＜中間体２−５＞を用いて合成例８により化合物１３を合成した。 Synthesis Example 18 Synthesis of Compound 13 Compound 13 was synthesized according to the following reaction formula.

Compound 13 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-5>.

  Mass [M + 1] = 1223

２−ブロモ−９，９−ジメチル−９Ｈ−フルオレンと９，９−ジメチル−９Ｈ−フルオレン−２−アミンを用いて前記合成例７と同様に実施して、＜中間体２−６＞を合成した。 Synthesis Example 19 Synthesis of Intermediate 2-6 Intermediate 2-6 was synthesized according to the following reaction formula.

<Intermediate 2-6> was synthesized in the same manner as in Synthesis Example 7 using 2-bromo-9,9-dimethyl-9H-fluorene and 9,9-dimethyl-9H-fluoren-2-amine. did.

  Mass [M + 1] = 402

＜中間体１−６＞と＜中間体２−６＞を用いて合成例８により化合物１５を合成した。 Synthesis Example 20 Synthesis of Compound 15 Compound 15 was synthesized according to the following reaction formula.

Compound 15 was synthesized according to Synthesis Example 8 using <Intermediate 1-6> and <Intermediate 2-6>.

  Mass [M + 1] = 1295

３−ブロモナフタレン−２−オールと（２−クロロ−６−フルオロフェニル）ボロン酸を用いて前記合成例１と同様に実験して、＜中間体４−１＞を合成した。 Synthesis Example 21 Synthesis of Intermediate 4-1 Intermediate 4-1 was synthesized according to the following reaction formula.

<Intermediate 4-1> was synthesized in the same manner as in Synthesis Example 1 using 3-bromonaphthalen-2-ol and (2-chloro-6-fluorophenyl) boronic acid.

  Mass [M + 1] = 273

１Ｌフラスコに、＜中間体３−１＞（３２．０ｇ、０．１５３ｍｏｌ）とポタシウムカーボネート（６３．４ｇ、０．４５９ｍｏｌ）を投入後、ジメチルアセトアミド（４００ｍＬ）で希釈し還流撹拌して、３時間反応後に終了した。反応溶媒を減圧蒸留した後、エチルアセテートと水で抽出して得られた有機層を無水硫酸マグネシウム処理後、濾過濃縮して、エチルアセテート、エタノール溶媒で再結晶して、＜中間体４−２＞（３３．０ｇ、収率８５％）を得た。 Synthesis Example 22 Synthesis of Intermediate 4-2 Intermediate 4-2 was synthesized according to the following reaction formula.

<Intermediate 3-1> (32.0 g, 0.153 mol) and potassium carbonate (63.4 g, 0.459 mol) were added to a 1 L flask, diluted with dimethylacetamide (400 mL), stirred at reflux, and 3 Ended after a time reaction. After the reaction solvent was distilled under reduced pressure, the organic layer obtained by extraction with ethyl acetate and water was treated with anhydrous magnesium sulfate, filtered and concentrated, and recrystallized with ethyl acetate and ethanol solvent. > (33.0 g, yield 85%) was obtained.

  Mass [M + 1] = 253

０．５Ｌフラスコに、＜中間体３−２＞（１７．０ｇ、０．０６７ｍｏｌ）とテトラヒドロフラン（１８０ｍＬ）を入れて、アセトン−ドライアイス浴に入れて内部温度を−７８℃に冷やした後、２．５Ｍノルマルブチルリチウム（３０．９ｍＬ、０．０７７ｍｏｌ）を徐々に滴下した後、１時間撹拌した。この後、トリメチルボレート（９．０ｍＬ、０．０８１ｍｏｌ）を徐々に滴加した後、３０分さらに撹拌した。この後、１６ｈ後に反応を終了し、水で処理後、エチルアセテートと塩水で抽出して得られた有機層を無水硫酸マグネシウム処理後、濾過濃縮して、エチルアセテート、ノルマルヘキサンで再結晶して、＜中間体４−３＞（１１．７ｇ、収率５９％）を得た。 Synthesis Example 23 Synthesis of Intermediate 4-3 Intermediate 4-3 was synthesized according to the following reaction formula.

<Intermediate 3-2> (17.0 g, 0.067 mol) and tetrahydrofuran (180 mL) were placed in a 0.5 L flask, and the mixture was placed in an acetone-dry ice bath to cool the internal temperature to -78 ° C. 2.5M normal butyl lithium (30.9 mL, 0.077 mol) was gradually added dropwise, followed by stirring for 1 hour. Thereafter, trimethyl borate (9.0 mL, 0.081 mol) was gradually added dropwise, and the mixture was further stirred for 30 minutes. After this, the reaction was terminated after 16 hours, treated with water, extracted with ethyl acetate and brine, the organic layer obtained was treated with anhydrous magnesium sulfate, filtered and concentrated, and recrystallized with ethyl acetate and normal hexane. <Intermediate 4-3> (11.7 g, yield 59%) was obtained.

  Confirmed by TLC and HPLC

＜中間体４−３＞を用いて前記合成例１と同様に実験して、＜中間体４−４＞を合成した。 Synthesis Example 24 Synthesis of Intermediate 4-4 Intermediate 4-4 was synthesized according to the following reaction formula.

<Intermediate 4-3> was synthesized in the same manner as in Synthesis Example 1 using <Intermediate 4-3>.

  Mass [M + 1] = 391

＜中間体４−４＞を用いて前記合成例２と同様に実験して、＜中間体４−５＞を合成した。 Synthesis Example 25 Synthesis of Intermediate 4-5 Intermediate 4-5 was synthesized according to the following reaction formula.

<Intermediate 4-4> was used in the same manner as in Synthesis Example 2 to synthesize <Intermediate 4-5>.

  Confirmed by TLC and HPLC

＜中間体４−５＞を用いて前記合成例３と同様に実験して、＜中間体４−６＞を合成した。 Synthesis Example 26 Synthesis of Intermediate 4-6 Intermediate 4-6 was synthesized according to the following reaction formula.

<Intermediate 4-5> was synthesized in the same manner as in Synthesis Example 3 using <Intermediate 4-5>.

  Mass [M + 1] = 389

＜中間体４−６＞を用いて前記合成例５と同様に実験して、＜中間体４−７＞を合成した。 Synthesis Example 27 Synthesis of Intermediate 4-7 Intermediate 4-7 was synthesized according to the following reaction formula.

<Intermediate 4-6> was used in the same manner as in Synthesis Example 5 to synthesize <Intermediate 4-7>.

  Mass [M + 1] = 632

＜中間体４−７＞を用いて前記合成例６と同様に実験して、＜中間体４−８＞を合成した。 Synthesis Example 28 Synthesis of Intermediate 4-8 Intermediate 4-8 was synthesized according to the following reaction formula.

<Intermediate 4-8> was synthesized in the same manner as in Synthesis Example 6 using <Intermediate 4-7>.

  Mass [M + 1] = 614

＜中間体４−８＞と＜中間体２−２＞を用いて前記合成例８と同様に実験して、＜化合物２５＞を合成した。 Synthesis Example 29: Synthesis of Compound 25 Compound 25 was synthesized according to the following reaction formula.

<Compound 25> was synthesized in the same manner as in Synthesis Example 8 using <Intermediate 4-8> and <Intermediate 2-2>.

  Mass [M + 1] = 1105

ジベンゾ［ｂ，ｄ］チオフェン−１−イルボロン酸を用いて前記合成例１と同様に実験して、＜中間体５−１＞を合成した。 Synthesis Example 30 Synthesis of Intermediate 5-1 Intermediate 5-1 was synthesized according to the following reaction formula.

<Intermediate 5-1> was synthesized in the same manner as in Synthesis Example 1 using dibenzo [b, d] thiophen-1-ylboronic acid.

  Mass [M + 1] = 323

＜中間体５−１＞を用いて前記合成例３と同様に実験して、＜中間体５−２＞を合成した。 Synthesis Example 31 Synthesis of Intermediate 5-2 Intermediate 5-2 was synthesized according to the following reaction formula.

<Intermediate 5-2> was synthesized in the same manner as in Synthesis Example 3 using <Intermediate 5-1>.

  Confirmed by TLC and HPLC

＜中間体５−２＞を用いて前記合成例３と同様に実験して、＜中間体５−３＞を合成した。 Synthesis Example 32 Synthesis of Intermediate 5-3 Intermediate 5-3 was synthesized according to the following reaction formula.

<Intermediate 5-2> was used in the same manner as in Synthesis Example 3 to synthesize <Intermediate 5-3>.

  Mass [M + 1] = 321

＜中間体５−３＞を用いて前記合成例４と同様に実験して、＜中間体５−４＞を合成した。 Synthesis Example 33 Synthesis of Intermediate 5-4 Intermediate 5-4 was synthesized according to the following reaction formula.

<Intermediate 5-3> was synthesized in the same manner as in Synthesis Example 4 using <Intermediate 5-3>.

  Mass [M + 1] = 321

＜中間体５−４＞を用いて前記合成例５と同様に実験して、＜中間体５−５＞を合成した。 Synthesis Example 34 Synthesis of Intermediate 5-5 Intermediate 5-5 was synthesized according to the following reaction formula.

<Intermediate 5-5> was synthesized in the same manner as in Synthesis Example 5 using <Intermediate 5-4>.

  Mass [M + 1] = 642

＜中間体５−５＞を用いて前記合成例６と同様に実験して、＜中間体５−６＞を合成した。 Synthesis Example 35 Synthesis of Intermediate 5-6 Intermediate 5-6 was synthesized according to the following reaction formula.

<Intermediate 5-6> was synthesized in the same manner as in Synthesis Example 6 using <Intermediate 5-5>.

  Mass [M + 1] = 624

＜中間体５−６＞と＜中間体２−３＞を用いて前記合成例８と同様に実験して、＜化合物１８＞を合成した。 Synthesis Example 36 Synthesis of Compound 18 Compound 18 was synthesized according to the following reaction formula.

<Compound 18> was synthesized in the same manner as in Synthesis Example 8 using <Intermediate 5-6> and <Intermediate 2-3>.

  Mass [M + 1] = 1138

  By a method similar to the synthesis method described in the synthesis example, in addition to the compound synthesized in the synthesis example, a compound corresponding to chemical formula 1 of the present application can be synthesized. Mass data of Compound 10 is shown in FIG.

<Example>

Example 1.
A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 mm was placed in distilled water in which a dispersant was dissolved and ultrasonically cleaned. The detergent is Fischer Co. The distilled water is Millipore Co. Distilled water that was secondarily filtered through a product filter was used. After washing ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

  On the ITO transparent electrode thus prepared, the HAT was deposited by thermal vacuum deposition to a thickness of 50 mm to form a hole injection layer. On top of that, HT-A1000Å was vacuum-deposited as a hole transport layer, and then HT-B was deposited to a thickness of 100Å. The light emitting layer was doped with 2 to 10 wt% of HA and Compound 1 as a host and vacuum-deposited to a thickness of 200 mm. Thereafter, ET-A and Liq were vapor-deposited in a ratio of 1: 1, and then, on top of that, in turn, 150% thick silver (Ag) 10% doped magnesium (Mg), and 1,000% Thick aluminum was deposited to form a cathode, and an organic light emitting device was manufactured.

  In the above process, the deposition rate of the organic substance was maintained at 1 Å / sec, LiF was maintained at 0.2 Å / sec, and aluminum was maintained at 3 Å / sec to 7 Å / sec.

Example 2
An organic light emitting device was manufactured in the same manner as in Example 1 except that Compound 7 was used instead of Compound 1 in Example 1.

Example 3 FIG.
An organic light emitting device was manufactured in the same manner as in Example 1 except that Compound 13 was used instead of Compound 1 in Example 1.

Example 4
An organic light emitting device was manufactured in the same manner as in Example 1 except that Compound 28 was used instead of Compound 1 in Example 1.

Embodiment 5 FIG.
An organic light emitting device was manufactured in the same manner as in Example 1 except that Compound 29 was used instead of Compound 1 in Example 1.

Example 6
An organic light emitting device was manufactured in the same manner as in Example 1 except that Compound 30 was used instead of Compound 1 in Example 1.

Example 7
An organic light emitting device was manufactured in the same manner as in Example 1 except that H-B was used instead of Compound HA in Example 1.

Example 8 FIG.
An organic light emitting device was manufactured in the same manner as in Example 7 except that Compound 7 was used instead of Compound 1 in Example 7.

Example 9
An organic light emitting device was manufactured in the same manner as in Example 7 except that Compound 13 was used instead of Compound 1 in Example 7.

Example 10
An organic light emitting device was manufactured in the same manner as in Example 7 except that Compound 28 was used instead of Compound 1 in Example 7.

Example 11
An organic light emitting device was manufactured in the same manner as in Example 7 except that Compound 29 was used instead of Compound 1 in Example 7.

Example 12
An organic light emitting device was manufactured in the same manner as in Example 7 except that Compound 30 was used instead of Compound 1 in Example 7.

Example 13
An organic light emitting device was manufactured in the same manner as in Example 1 except that HC was used instead of HA in Example 1.

Example 14
An organic light emitting device was manufactured in the same manner as in Example 13 except that Compound 7 was used instead of Compound 1 in Example 13.

Example 15.
An organic light emitting device was manufactured in the same manner as in Example 13 except that Compound 13 was used instead of Compound 1 in Example 13.

Example 16
An organic light emitting device was manufactured in the same manner as in Example 13 except that Compound 28 was used instead of Compound 1 in Example 13.

Example 17.
An organic light emitting device was manufactured in the same manner as in Example 13 except that Compound 29 was used instead of Compound 1 in Example 13.

Example 18
An organic light emitting device was manufactured in the same manner as in Example 13 except that Compound 30 was used instead of Compound 1 in Example 13.

Comparative Example 1
An organic light emitting device was produced in the same manner as in Example 1 except that D-1 was used instead of Compound 1 in Example 1.

Comparative Example 2
An organic light emitting device was produced in the same manner as in Example 1 except that D-2 was used instead of Compound 1 in Example 1.

Comparative Example 3
An organic light emitting device was manufactured in the same manner as in Example 1 except that D-3 was used instead of Compound 1 in Example 1.

Comparative Example 4
An organic light emitting device was produced in the same manner as in Example 7 except that D-1 was used instead of Compound 1 in Example 7.

Comparative Example 5
An organic light emitting device was produced in the same manner as in Example 7 except that D-2 was used instead of Compound 1 in Example 7.

Comparative Example 6
An organic light emitting device was produced in the same manner as in Example 7 except that D-3 was used instead of Compound 1 in Example 7.

Comparative Example 7
An organic light emitting device was produced in the same manner as in Example 13 except that D-1 was used instead of Compound 1 in Example 13.

Comparative Example 8
An organic light emitting device was manufactured in the same manner as in Example 13 except that D-2 was used instead of Compound 1 in Example 13.

Comparative Example 9
An organic light emitting device was manufactured in the same manner as in Example 13 except that D-3 was used instead of Compound 1 in Example 13.

The organic light emitting devices of Examples 1 to 18 and Comparative Examples 1 to 9 were measured for driving voltage and luminous efficiency at a current density of 10 mA / cm, and the initial luminance was 95% at a current density of 20 mA / cm. Time (LT95) was measured. The results are shown in Table 1 below.

  When Examples 1 to 18 and Comparative Examples 1 to 9 in Table 1 are compared, in the case of an organic light emitting device manufactured by including the heterocyclic compound represented by Chemical Formula 1, the intermolecular structure is determined by a three-dimensional structure. It shows excellent performance by preventing inter-molecular fluorescence decay due to dense stacking. In addition, in the state of losing one electron, the electron density distribution of HOMO is generally distributed in the spiroindoloacridine portion containing nitrogen, which is known to have a stable cation state. Has brought improvements. Therefore, it was confirmed that the organic light-emitting devices manufactured in Comparative Examples 1 to 9 containing a pyrene-based or fluorene-based compound were superior in efficiency and life characteristics.

1: Substrate 2: Anode 3: Light-emitting layer 4: Cathode 5: Hole injection layer 6: Hole transport layer 7: Electron transport layer

Claims (17)

Heterocyclic compound represented by the following chemical formula 1:
[Chemical Formula 1]

In Formula 1,
R5 to R8 are the same or different from each other, and are independently hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkylsulfoxy group, aryl Silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted aralkyl A substituted or unsubstituted alkylamine group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted heterocyclic group,
L1 and L2 are the same or different from each other and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group;
Ar1 is a substituted or unsubstituted hydrocarbon ring group; or a substituted or unsubstituted heterocyclic group;
R1 to R4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
a and b are each an integer of 0 to 4,
c and d are integers of 0 to 3,
when a to d are each 2 or more, the substituents in parentheses are the same or different from each other;
n1 and n2 are each 0 or 1,
1 or more of n1 and n2 is an integer of 1,
X1 and X2 are hydrogen or are directly bonded to each other. The heterocyclic compound according to claim 1, wherein Ar1-L2-NR3R4 is one of the following structures:

In the structure,
The definitions of L2, R3, and R4 are the same as the definitions in Chemical Formula 1,
R ′ and R ″ are the same as or different from each other, and are independently hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, alkylsulfoxy group Arylsulfoxy group; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; substituted or unsubstituted Substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine group; substituted or unsubstituted arylheteroarylamine A group; a substituted or unsubstituted arylphosphine group; Other is a substituted or unsubstituted heterocyclic group,
The structure may be further substituted.   L1 and L2 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms. The heterocyclic compound according to claim 1 or 2. The heterocyclic compound according to claim 1 or 2, wherein L1 and L2 are the same or different from each other and are each independently a direct bond; or one of the substituents described below:

.   R1 to R4 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. 5. The heterocyclic compound according to any one of 4 above. The heterocyclic compound according to any one of claims 1 to 4, wherein R1 to R4 are the same as or different from each other, and are each independently any one of the following structures:

In the structure,
R201 to R297 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; nitrile group; nitro group; silyl group; boron group; substituted or unsubstituted amine group; A substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
a1, a6, a10, a23 and a25 are each an integer of 0 to 5,
a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are each an integer of 0 to 4,
a3 and a22 are each an integer of 0 to 7,
a4, a7, a12, a15, a19, a26 and a27 are each an integer of 0 to 3,
a11 is an integer of 0 to 9,
a13, a20 and a24 are each an integer of 0 to 6,
a18, b5, b10, b14 and b16 are each an integer of 0 to 2,
when a18, b5, b10, b14 and b16 are 2, the substituents in parentheses are different from each other;
a1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28-a35, b1-b4, b6-b9, b11-b13, b15, b17-b32, a3, When a22, a4, a7, a12, a15, a19, a26, a27, a11, a13, a20 and a24 are each 2 or more, the substituents in parentheses are the same or different from each other. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is selected from the following compounds:

.   A first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers are defined in claims 1 to 7. The organic light emitting element containing the heterocyclic compound of any one of these. The organic layer includes a hole injection layer or a hole transport layer,
The organic light emitting device according to claim 8, wherein the hole injection layer or the hole transport layer includes the heterocyclic compound of Formula 1. The organic material layer includes an electron transport layer or an electron injection layer,
10. The organic light-emitting device according to claim 8, wherein the electron transport layer or the electron injection layer includes the heterocyclic compound represented by Formula 1. The organic layer includes a light emitting layer,
The organic light emitting device according to any one of claims 8 to 10, wherein the light emitting layer contains the heterocyclic compound represented by Chemical Formula 1. The organic light emitting device according to claim 11, wherein the light emitting layer further includes a compound of the following chemical formula 2.
[Chemical formula 2]

In Formula 2,
R9 represents hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, arylsulfoxy group, silyl group, boron group, substituted Or a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; a substituted or unsubstituted arylphosphine group; Or an unsubstituted heterocyclic group,
p is an integer of 0-6,
when p is 2 or more, the substituents in parentheses are the same or different from each other;
L3 to L6 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
Ar2 to Ar5 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. The organic light emitting device according to claim 12, wherein L3 to L6 are the same or different from each other, and are each independently selected from a direct bond; or the following structure:

. The organic light emitting device according to claim 12 or 13, wherein the Ar2 to Ar5 are the same or different from each other, and are independently selected from hydrogen; or the following structure:

. The organic light-emitting device according to claim 11, wherein the light-emitting layer further includes a compound represented by Chemical Formula 3 below.
[Chemical formula 3]

In Formula 3,
R10 represents hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxy group, aryloxy group, alkylthioxy group, arylthioxy group, arylsulfoxy group, silyl group, boron group, substituted Or a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylheteroarylamine group; a substituted or unsubstituted arylphosphine group; Or an unsubstituted heterocyclic group,
q is an integer of 0 to 7,
when q is 2 or more, the substituents in parentheses are the same or different from each other;
L7 to L9 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar6 to Ar8 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. The organic light emitting device according to claim 15, wherein L7 to L9 are the same or different from each other, and are each independently selected from a direct bond; or the following structure:

. The organic light emitting device according to claim 15 or 16, wherein the Ar6 to Ar8 are the same or different from each other and are independently selected from the following structures:

.

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