JP6628066B2 - Heterocyclic compound and organic light emitting device containing the same - Google Patents

Description

  The present specification claims the benefit of priority based on Korean Patent Application No. 10-2016-0030406 filed with the Korean Patent Office on March 14, 2016, and discloses the contents disclosed in the Korean Patent Application literature. Are all incorporated as part of the present specification.

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

  In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light-emitting device using the organic light-emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer therebetween. Here, the organic material layer often has a multilayer structure composed of different substances in order to enhance the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, and a light emitting layer. , An electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer at the positive electrode and electrons are injected into the organic material layer at the negative electrode. When the injected holes come into contact with the electrons, excitons are formed. Is formed and light is emitted when the exciton returns to the ground state again.

  There is a continuing need to develop new materials for such organic light emitting devices.

  This specification describes a heterocyclic compound and an organic light-emitting device including the same.

前記化学式１中、
Ｒ_１およびＲ_２は、互いに同一でも異なっていてもよく、それぞれ独立して、置換または非置換のアルキル基；または置換または非置換のアリール基であるか、Ｒ_１およびＲ_２が互いに結合して置換または非置換の環を形成し、
Ｌ_１およびＬ_２は、互いに同一でも異なっていてもよく、それぞれ独立して、置換または非置換のアリーレン基；または置換または非置換のヘテロアリーレン基であり、
ｍおよびｎは、互いに同一でも異なっていてもよく、それぞれ独立して、０〜５の整数であり、
ｍが２以上の場合、Ｌ_１は、互いに同一でも異なっていてもよく、
ｎが２以上の場合、Ｌ_２は、互いに同一でも異なっていてもよく、
Ａｒ_１およびＡｒ_２は、互いに同一でも異なっていてもよく、それぞれ独立して、水素；置換または非置換のアリール基；置換または非置換のアリールアミン基；置換または非置換のヘテロ環基；または置換または非置換のホスフィンオキシド基であり、
Ｒ、Ｒ´およびＲ´´は、互いに同一でも異なっていてもよく、それぞれ独立して、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；カルボニル基；エステル基；イミド基；アミノ基；置換または非置換のシリル基；置換または非置換のホウ素基；置換または非置換のアルキル基；置換または非置換のシクロアルキル基；置換または非置換のアリールオキシ基；置換または非置換のアルコキシ基；置換または非置換のアリールオキシ基；置換または非置換のアルケニル基；置換または非置換のアラルキル基；置換または非置換のアルキルアリール基；置換または非置換のアルキルアミン基；置換または非置換のアラルキルアミン基；置換または非置換のヘテロアリールアミン基；置換または非置換のアリールアミン基；置換または非置換のアリールホスフィン基；置換または非置換のホスフィンオキシド基；置換または非置換のアリール基；置換または非置換のヘテロ環基であり、
ａおよびｂは、互いに同一でも異なっていてもよく、それぞれ独立して、０〜４の整数であり、
ａが２以上の場合、Ｒ´は、互いに同一でも異なっていてもよく、
ｂが２以上の場合、Ｒ´´は、互いに同一でも異なっていてもよい。 One embodiment of the present specification provides a compound represented by Formula 1 below.
[Chemical formula 1]

In the above chemical formula 1,
R ₁ and R ₂ may be the same or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or R ₁ and R ₂ are bonded to each other. To form a substituted or unsubstituted ring;
L ₁ and L ₂ may be the same or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
m and n may be the same or different from each other, and are each independently an integer of 0 to 5,
When m is 2 or more, L ₁ may be the same or different from each other;
When n is 2 or more, L ₂ may be the same or different from each other;
Ar ₁ and Ar ₂ may be the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heterocyclic group; A substituted or unsubstituted phosphine oxide group,
R, R 'and R "may be the same or different from each other, and each independently represents hydrogen; deuterium; halogen; nitrile; nitro; hydroxy; carbonyl; ester; Substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted Substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl group; substituted or unsubstituted alkylaryl group; substituted or unsubstituted alkylamine group; substituted or unsubstituted Aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine group; Other unsubstituted aryl phosphine group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group
a and b may be the same or different from each other, and are each independently an integer of 0 to 4;
When a is 2 or more, R's may be the same or different from each other;
When b is 2 or more, R ″ may be the same or different from each other.

  One embodiment of the present specification is directed to an organic material including a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode. An organic light emitting device, wherein at least one of the organic layers includes the compound of Formula 1.

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

FIG. 2 is a diagram illustrating an example of an organic light emitting device including a substrate 1, a positive electrode 2, a light emitting layer 3, and a negative electrode 4. FIG. 2 is a diagram illustrating an example of an organic light emitting device including a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a negative electrode 4.

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

  One embodiment of the present specification provides a compound represented by Formula 1.

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

  As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen; nitrile; nitro; hydroxy; carbonyl; ester; imide; amino; phosphine oxide; Aryloxy group; alkylthioxy group; arylthioxy group; alkylsulfoxy group; arylsulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; An alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; and a substituted or unsubstituted or substituted one or more substituents selected from the group consisting of a heterocyclic group. May be present, two or more of the substituents exemplified above are It refers to those binding have been substituted or unsubstituted. For example, "a substituent in which two or more substituents are linked" can be interpreted as an aryl group substituted with a heterocyclic group. As a more specific example, the “biphenyl group” may be one aryl group, and may be interpreted as a phenyl group substituted with a phenyl group.

  Herein, examples of halogen groups include fluorine, chlorine, bromine or iodine.

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

  In the present specification, a silyl group may be represented by a chemical formula of —SiRaRbRc, wherein Ra, Rb, and Rc are each hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. You may. Specific examples of the silyl group include trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl. However, the present invention is not limited to this.

  In the present specification, the boron group may be represented by a chemical formula of -BRaRb, wherein Ra and Rb are each a hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Good. 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 carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. In one embodiment, the alkyl group has 1 to 10 carbon atoms. In one embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1 -Ethyl-propyl, 1,1-dimethyl-propyl Pills, isohexyl, 4-methylhexyl, 5-methylhexyl there are such as, but not limited to.

  In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n- Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto. Not something.

  Substituents containing an alkyl group, an alkoxy group and other alkyl group moieties described in the present specification include both linear and branched ones.

  In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. In one embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3- Butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1- Yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.

  In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethyl Examples include, but are not limited to, cyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

  In this specification, the number of carbon atoms of the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, and a diphenylamine group. Phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, and the like, 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, and 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 simultaneously.

  Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine, diphenylamine But not limited to, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, carbazole 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, and a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group containing two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group simultaneously.

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

  In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, and a substituted or unsubstituted triarylphosphine group. The aryl group in the aryl phosphine 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 simultaneously.

  In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as, but not limited to, a phenyl group, a biphenyl group, and a terphenyl group. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like.

  In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

、

などのスピロフルオレニル基、

（９，９‐ジメチルフルオレニル基）、
および

（９，９‐ジフェニルフルオレニル基）
などの置換されたフルオレニル基であってもよい。ただし、これに限定されるものではない。 When the fluorenyl group is substituted,

,

Spirofluorenyl groups such as

(9,9-dimethylfluorenyl group),
and

(9,9-diphenylfluorenyl group)
Or a substituted fluorenyl group. However, it is not limited to this.

  In the present specification, a heterocyclic group is a heterocyclic group containing at least one of N, O, P, S, Si and Se as a hetero atom, and the number of carbon atoms is not particularly limited. ~ 60 is preferred. According to one embodiment, the heterocyclic group has 1 to 30 carbon atoms. Examples of heterocyclic groups include pyridyl, pyrrole, pyrimidyl, pyridazinyl, furanyl, thiophenyl, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxa Diazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl Group, naphthyridinyl group, acridyl group, xanthenyl group, phenanthridinyl group, diazanaphthalenyl group, triazaindenyl group, indole group, indolinyl group, indolizinyl group, phthalazinyl group, Ridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group, benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazole group, benzocarbazole group, Dibenzocarbazole group, indolocarbazole group, indenocarbazole group, phenazinyl group, imidazopyridine group, phenoxazinyl group, phenanthridine group, phenanthroline group, phenothiazine group, imidazopyridine group, imidazophenanthridine group , A benzimidazoquinazoline group, or a benzimidazophenanthridine group, but is not limited thereto.

  In one embodiment of the present specification, the heterocyclic group has 3 to 60 ring elements. In one embodiment, the heterocyclic group has 3 to 40 ring elements. In one embodiment, the heterocyclic group has 3 to 20 ring elements.

  In the present specification, the description regarding the heterocyclic group described above can be applied except that the heteroaryl group is aromatic.

  In the present specification, an aryl group in an aryloxy group, an arylthioxy group, an arylsulfoxy group, an arylphosphine group, an aralkyl group, an aralkylamine group, an aralkenyl group, an alkylaryl group, an arylamine group, and an arylheteroarylamine group For the above, the description regarding the above aryl group can be applied.

  In the present specification, the above description regarding the alkyl group can be applied to the alkyl group in the alkylthioxy group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group, and the alkylamine group.

  In the present specification, for the heteroaryl group, the heteroarylamine group, and the heteroaryl group in the arylheteroarylamine group, the description regarding the heterocyclic group described above can be applied.

  In the present specification, the description regarding the alkenyl group described above can be applied to the alkenyl group in the aralkenyl group.

  In the present specification, the above description regarding the aryl group can be applied except that the arylene group is a divalent group.

  In the present specification, the above description regarding the heterocyclic group can be applied except that the heteroarylene group is an aromatic divalent group.

  In the present specification, the aliphatic hydrocarbon ring means a ring composed of only carbon and hydrogen atoms as a non-aromatic ring. Specifically, examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like. However, the present invention is not limited to these.

  In the present specification, the aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. Specifically, examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. And the like, but are not limited to these.

  As used herein, the term "aliphatic heterocycle" means an aliphatic ring containing one or more heteroatoms. Specifically, examples of the aliphatic heterocyclic ring include oxirane, tetrahydrofuran, 1,4-dioxane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxepane, azocaine, thiocaine, and the like. However, the present invention is not limited to these.

  In the present specification, an aromatic hetero ring means an aromatic ring containing one or more hetero atoms. Specifically, examples of the aromatic heterocycle include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, Tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolizine, benzo Thiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzo carbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, there are such indeno carbazole, but is not limited thereto.

  In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.

［化学式Ｂ］

前記化学式Ａおよび化学式Ｂ中、
Ｒ_１、Ｒ_２、Ｌ_１、Ｌ_２、ｍ、ｎ、Ａｒ_１、Ａｒ_２、Ｒ、Ｒ´およびＲ´´の定義は、化学式１および化学式２における定義と同じである。 In one embodiment of the present specification, the compound represented by Formula 1 may be represented by Formula A or Formula B below.
[Chemical formula A]

[Chemical formula B]

In the chemical formulas A and B,
The definitions of R ₁ , R ₂ , L ₁ , L ₂ , m, n, Ar ₁ , Ar ₂ , R, R ′ and R ″ are the same as those in Chemical Formulas 1 and 2.

In one embodiment of the present specification, L ₁ and L ₂ may be the same or different and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

前記構造は、重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；カルボニル基；エステル基；イミド基；アミン基；ホスフィンオキシド基；アルコキシ基；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；アルキル基；シクロアルキル基；アルケニル基；アリール基；アラルキル基；アラルケニル基；アルキルアリール基；アルキルアミン基；アラルキルアミン基；ヘテロアリールアミン基；アリールアミン基；アリールヘテロアリールアミン基；アリールホスフィン基；およびヘテロ環基からなる群から選択された１個以上の置換基で置換されていてもよくまたは非置換であってもよい。 Further, in the present specification, L ₁ and L ₂ may be the same or different from each other, and are preferably each independently any one linking group selected from the following group. Without being limited, the following structures may be further substituted.

The structure is deuterium; halogen; nitrile; nitro; hydroxy; carbonyl; ester; imide; amine; phosphine oxide; alkoxy; aryloxy; alkylthioxy; Alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkyl, alkylaryl, alkylamine, alkylamine, aralkylamine, heteroaryl. An aryl group; an arylamine group; an arylheteroarylamine group; an arylphosphine group; and a heterocyclic group, which may be substituted or unsubstituted with one or more substituents.

In one embodiment of the present specification, L ₁ and L ₂ may be the same or different from each other and are each independently a substituted or unsubstituted phenylene group; a substituted or unsubstituted pyridylene group; a substituted or unsubstituted Substituted or unsubstituted triazinylene group; substituted or unsubstituted carbazolene group; substituted or unsubstituted dibenzofuranylene group; or substituted or unsubstituted dibenzothiophenylene group.

According to one embodiment of the present specification, Ar ₁ and Ar ₂ may be the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group A substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted phosphine oxide group.

According to an embodiment of the present specification, Ar ₁ and Ar ₂ may be the same or different from each other, and may be independently any one selected from the following structures. The following structures may be further substituted.

  Specifically, the structure is deuterium; halogen; nitrile; nitro; hydroxy; carbonyl; ester; imide; amine; phosphine oxide; alkoxy; aryloxy; Arylthioxy group; alkylsulfoxy group; arylsulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; An amine group; a heteroarylamine group; an arylamine group; an arylheteroarylamine group; an arylphosphine group; and optionally substituted with one or more substituents selected from the group consisting of a heterocyclic group. There may be.

According to an embodiment of the present specification, Ar ₁ and Ar ₂ may be the same or different from each other, and each independently includes hydrogen; a phenyl group; a phenyl group, a pyridine group, a quinoline group, and a quinazoline group. A phenyl group substituted with one or more substituents selected from the group; a biphenyl group; a naphthyl group; an anthracenyl group; an anthracenyl group substituted with a phenyl group; a pyridine group; a phenyl group and a biphenyl group. A pyridine group substituted with one or more substituents; a pyrimidine group; a pyrimidine group substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; a triazine group; a group consisting of a phenyl group and a biphenyl group. A triazine group substituted with one or more substituents selected from the group consisting of: a benzimidazole group; Quinoline group substituted with phenyl group; quinazoline group; quinazoline group substituted with phenyl group; carbazole group; selected from the group consisting of phenyl group, biphenyl group and naphthyl group. A carbazole group substituted with one or more selected groups; a dibenzofuran group; a dibenzothiophene group; an amine group substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a fluorene group; Phosphine oxide group.

According to one embodiment, Ar ₁ is a phenyl group; a naphthyl group; a pyridine group; a pyridine group substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; a pyrimidine group; A pyrimidine group substituted with one or more substituents selected from the group consisting of biphenyl groups; a triazine group; a triazine group substituted with one or more substituents selected from the group consisting of phenyl and biphenyl groups; Or a carbazole group substituted by one or more selected from the group consisting of a phenyl group, a biphenyl group and a naphthyl group.

According to one embodiment, Ar ₂ is hydrogen; phenyl; phenyl substituted with one or more substituents selected from the group consisting of phenyl, pyridine, quinoline and quinazoline; biphenyl; anthracenyl Group; anthracenyl group substituted with phenyl group; pyridine group; pyridine group substituted with one or more substituents selected from the group consisting of phenyl group and biphenyl group; pyrimidine group; A pyrimidine group substituted with one or more selected substituents; a triazine group; a triazine group substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; a benzimidazole group; Benzoimidazole group; quinoline group; quinoline group substituted by phenyl group; A quinazole group substituted with a phenyl group; a carbazole group; an amine group substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group and a fluorene group; a carbazole group substituted with a phenyl group A dibenzofuran group; a dibenzothiophene group; or a phosphine oxide group substituted with a phenyl group.

According to one embodiment of the present specification, R ₁ and R ₂ may be the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Alternatively, R ₁ and R ₂ may combine with each other to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, R ₁ and R ₂ may be the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. .

According to one embodiment, R ₁ and R ₂ may be the same or different from each other, and are each independently an alkyl group or an aryl group.

According to one embodiment, R ₁ and R ₂ may be the same or different and are each independently a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

According to one embodiment, R ₁ and R ₂ may be the same or different from each other, and are each independently a methyl group; or a phenyl group.

  In one embodiment of the present specification, R, R ′ and R ″ may be the same or different from each other, and are each independently a hydrogen; an alkyl group; an aryl group; or a heterocyclic group.

  In one embodiment, R, R 'and R "are all hydrogen.

In one embodiment of the present invention, the compound of Formula 1 may be one selected from the following compounds.

  The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy band gap.

  In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure. In the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents into the core structure.

  The compound represented by Formula A or Formula B can be synthesized using a reaction represented by the following general formula, but is not limited thereto.

  (1) General method for synthesizing a compound represented by Chemical Formula A

(I)

(Ii)

(Iii)

(Iv) -1

(Iv) -2

  (2) General synthesis method of the compound represented by the chemical formula B

(I)

(Ii)

(Iii)

(Iv) -1 '

(Iv) -2 '

Ar _{3 to} Ar ₆ may be the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted phosphine oxide group, and the description regarding Ar ₁ and Ar ₂ can be applied.

  In addition, by introducing various substituents into the core structure having the above-described structure, a compound having a specific property of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material and the electron transport layer material used in the production of the organic light emitting device into the core structure, A substance that satisfies the conditions required for the organic layer can be synthesized.

  Further, the organic light emitting device according to the present invention is an organic light emitting device including a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode. A light emitting element, wherein at least one of the organic layers contains the compound.

  The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compounds.

  The compound may be formed on the organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the organic light emitting device. Here, the solution coating method means a spin coating method, a dip coating method, an ink jet printing method, a screen printing method, a spray method, a roll coating method, and the like, but is not limited thereto.

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

  Therefore, in the organic light emitting device of the present invention, the organic material layer may include one or more of a hole injection layer, a hole transport layer, and a layer that simultaneously performs hole injection and hole transport. One or more of the layers may contain the compound represented by Chemical Formula 1.

  In one embodiment, the organic material layer may include one or more of a hole injection layer, an electron suppression layer, a hole transport layer, and a layer that simultaneously performs hole injection and hole transport. One or more layers may contain the compound represented by the above-mentioned chemical formula 1.

  As another example, the organic layer may include an electron suppression layer, and the electron suppression layer may include a compound represented by Formula 1 above.

  In one embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 above. For example, the compound represented by Formula 1 may be included as a host of the light emitting layer. As another example, the compound represented by Formula 1 may be included as a phosphorescent host of the light emitting layer.

  As another example, the organic layer including the compound represented by Formula 1 may include the compound represented by Formula 1 as a host, and may include another organic compound, a metal, or a metal compound as a dopant.

  As another example, the organic layer containing the compound represented by Formula 1 may include the compound represented by Formula 1 as a host and may be used together with an iridium (Ir) dopant.

  In addition, the organic material layer may include one or more of an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection, and one or more of the layers may include the compound. .

  In one embodiment, the organic material layer of the organic electronic device includes a hole transport layer, and the hole transport layer includes a compound represented by Formula 1 above.

  In the organic layer having such a multilayer structure, the compound is used as a light-emitting layer, a layer that simultaneously performs hole injection / hole transport and light emission, a layer that simultaneously performs hole transport and light emission, or a layer that simultaneously performs electron transport and light emission. May be included.

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

  FIG. 1 illustrates the structure of an organic light emitting device in which a positive electrode 2, a light emitting layer 3, and a negative electrode 4 are sequentially stacked on a substrate 1. In such a structure, the compound may be included in the light emitting layer 3.

  FIG. 2 illustrates the structure of an organic light emitting device in which a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a negative electrode 4 are sequentially stacked on a substrate 1. I have. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, or the electron transport layer 7.

  For example, the organic light emitting device according to the present invention may be configured such that a metal or a conductive metal is deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. An oxide or an alloy thereof is deposited to form a positive electrode, and a hole injection layer, a hole transport layer, an organic layer including a light-emitting layer and an electron transport layer are formed thereon, and then a negative electrode is formed thereon. It can be manufactured by depositing a usable substance. In addition to this method, an organic light emitting element may be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

  The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, but is not limited thereto, and may have a single layer structure. In addition, the organic layer may be formed using various polymer materials, instead of a vapor deposition method, but by a solvent process, for example, a spin coating method, a dip coating method, a doctor blade method, a screen printing method, and an inkjet printing method. Alternatively, a smaller number of layers can be manufactured by a method such as a thermal transfer method.

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

As the negative electrode material, generally, a material having a small work function is preferable so that electrons can be easily injected into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; LiF / Al or LiO ₂ / Al However, the present invention is not limited to these.

  As the hole injecting material, a material that receives hole injection smoothly from the positive electrode at a low voltage, such as a HOMO (highest occupied molecular orbital) of the hole injecting material, is a combination of the work function of the positive electrode material and the HOMO of the surrounding organic material layer. It is preferably between. Specific examples of the hole injecting material include metal porphyrins, oligothiophenes, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, Examples include, but are not limited to, anthraquinone and polyaniline and polycompound-based conductive polymers.

  As the hole transporting substance, a substance having high mobility for holes is preferable as a substance capable of receiving holes from the positive electrode or the hole injection layer and transferring the holes to the light emitting layer. Specific examples include, but are not limited to, an arylamine-based organic substance, a conductive polymer, and a block copolymer in which a conjugated portion and a non-conjugated portion coexist.

  The light-emitting substance is a substance capable of emitting light in the visible light region by receiving and combining the transport of holes and electrons from the hole transport layer and the electron transport layer, respectively, and has good quantum efficiency for fluorescence and phosphorescence. Substances are preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compound; dimerized styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compound; benzoxazole, benzothiazole and benzimidazole. Poly (p-phenylenevinylene) (PPV) -based polymer; spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.

  The iridium-based complex used as the dopant of the light emitting layer is as follows.

[Ir (piq) 3] [Btp2Ir (acac)]

[Ir (ppy) 3] [Ir (ppy) 2 (acac)]

[Ir (mpyp) 3] [F2Irpic]

[(F2ppy) 2Ir (tmd)] [Ir (dfppz) 3]

  As the electron transporting material, a material having a high electron mobility is preferable as a material that can be smoothly injected from the negative electrode and transferred to the light emitting layer. Specific examples include, but are not limited to, an 8-hydroxyquinoline Al complex; a complex containing Alq3; an organic radical compound; and a hydroxyflavone-metal complex.

  The organic light emitting device according to the present invention may be of a top emission type, a rear emission type, or a dual emission type, depending on the material used.

  The compound according to the present invention can act on a principle similar to that applied to an organic light-emitting device in an organic electronic device such as an organic solar cell, an organic photoreceptor, an organic transistor and the like.

  The method for producing the compound of Formula 1 and the production of an organic light emitting device using the same will be specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereby.

<Synthesis Example 1> Synthesis of Intermediate An intermediate was synthesized by the following reaction.

  Synthesis of Intermediates A-1 and A-2

(I)

(Ii)

(Iii)

  Synthesis of Intermediates B-1 and B-2

(I)

(Ii)

(Iii)

  Synthesis of intermediates C-1 and C-2

(I)

(Ii)

(Iii)

  Synthesis of Intermediates D-1 and D-2

(I)

(Ii)

(Iii)

  Synthesis of Intermediates E-1 and E-2

(I)

(Ii)

(Iii)

  Synthesis of intermediates F-1 and F-2

(I)

(Ii)

(Iii)

  Synthesis of Intermediates G-1 and G-2

(I)

(Ii)

(Iii)

  Synthesis of intermediates H-1 and H-2

(I)

(Ii)

(Iii)

In the method for synthesizing the intermediates, various intermediates were synthesized as described below by appropriately changing the reactants.

  <Synthesis Example 1> Synthesis of compound of Formula 1

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ａ‐２（６．００ｇ、１２．６３ｍｍｏｌ）、Ｎ‐（［１，１´‐ビフェニル］‐４‐ｙｌ）‐Ｎ‐（４‐ブロモフェニル）‐［１，１´‐ビフェニル］‐４‐アミン（Ｎ‐（［１，１´‐ｂｉｐｈｅｎｙｌ］‐４‐ｙｌ）‐Ｎ‐（４‐ｂｒｏｍｏｐｈｅｎｙｌ）‐［１，１´‐ｂｉｐｈｅｎｙｌ］‐４‐ａｍｉｎｅ）（６．７４ｇ、１３．８９ｍｍｏｌ）をテトラヒドロフラン３２０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１６０ｍｌ）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（０．４４ｇ、０．３８ｍｍｏｌ）を入れた後、３時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させてテトラヒドロフラン２５０ｍｌで再結晶して化合物３（８．２２ｇ、８６％）を製造した。 Production Example 1: Synthesis of the following compound 3 [Compound 3]

Compound A-2 (6.00 g, 12.63 mmol), N-([1,1′-biphenyl] -4-yl) -N- (4-bromophenyl)-[ 1,1′-biphenyl] -4-amine (N-([1,1′-biphenyl) -4-yl) -N- (4-bromophenyl)-[1,1′-biphenyl] -4-amine After completely dissolving (6.74 g, 13.89 mmol) in 320 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (160 ml) was added, and tetrakis- (triphenylphosphine) palladium (0.44 g, 0.38 mmol) was added. Thereafter, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of tetrahydrofuran to obtain Compound 3 (8.22 g, 86%).

  MS [M + H] + = 755

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ｃ‐２（１１．００ｇ、１８．０６ｍｍｏｌ）、Ｎ‐（４‐ブロモフェニル）‐９，９‐ジメチル‐Ｎ‐フェニル‐９Ｈ‐フルオレン‐２‐アミン（Ｎ‐（４‐ｂｒｏｍｏｐｈｅｎｙｌ）‐９，９‐ｄｉｍｅｔｈｙｌ‐Ｎ‐ｐｈｅｎｙｌ‐９Ｈ‐ｆｌｕｏｒｅｎ‐２‐ａｍｉｎｅ）（７．５５ｇ、１７．１６ｍｍｏｌ）をテトラヒドロフラン２２０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１１０ｍｌ）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（０．２１ｇ、０．１８ｍｍｏｌ）を入れた後、３時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させ、テトラヒドロフラン２２０ｍｌで再結晶して化合物５（１２．２４ｇ、８０％）を製造した。 Production Example 2: Synthesis of the following compound 5 [Compound 5]

Compound C-2 (11.00 g, 18.06 mmol) and N- (4-bromophenyl) -9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (11.00 g, 18.06 mmol) were placed in a 500 ml round bottom flask under a nitrogen atmosphere. N- (4-bromophenyl) -9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (7.55 g, 17.16 mmol) was completely dissolved in 220 ml of tetrahydrofuran, and then a 2M aqueous solution of potassium carbonate ( Then, tetrakis- (triphenylphosphine) palladium (0.21 g, 0.18 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 ml of tetrahydrofuran to produce Compound 5 (12.24 g, 80%).

  MS [M + H] + = 843

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ｂ‐２（１２．００ｇ、２４．７４ｍｍｏｌ）、４‐ブロモ‐Ｎ，Ｎ‐ジフェニルアニリン（４‐ｂｒｏｍｏ‐Ｎ，Ｎ‐ｄｉｐｈｅｎｙｌａｎｉｌｉｎｅ）（７．５９ｇ、２３．５１ｍｍｏｌ）をテトラヒドロフラン２８０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１４０ｍｌ）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（０．８６ｇ、０．７４ｍｍｏｌ）を入れた後、３時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させ、テトラヒドロフラン１７０ｍｌで再結晶して化合物６（１１．０７ｇ、７４％）を製造した。 Production Example 3: Synthesis of the following compound 6 [Compound 6]

Compound B-2 (12.00 g, 24.74 mmol) and 4-bromo-N, N-diphenylaniline (4-bromo-N, N-diphenylaniline) (7.59 g, 23) were placed in a 500 ml round bottom flask under a nitrogen atmosphere. .51 mmol) was completely dissolved in 280 ml of tetrahydrofuran, a 2M aqueous solution of potassium carbonate (140 ml) was added, tetrakis- (triphenylphosphine) palladium (0.86 g, 0.74 mmol) was added, and the mixture was heated and stirred for 3 hours. did. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 170 ml of tetrahydrofuran to produce Compound 6 (11.07 g, 74%).

  MS [M + H] + = 603

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ａ‐２（１０．００ｇ、２０．６２ｍｍｏｌ）、２‐（３‐ブロモフェニル）‐４，６‐ジフェニル‐１，３，５‐トリアジン（２‐（３‐ｂｒｏｍｏｐｈｅｎｙｌ）‐４，６‐ｄｉｐｈｅｎｙｌ‐１，３，５‐ｔｒｉａｚｉｎｅ）（７．５８ｇ、１９．５９ｍｍｏｌ）をテトラヒドロフラン２８０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１４０ｍｌ）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（０．７１ｇ、０．６２ｍｍｏｌ）を入れた後、５時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させ、テトラヒドロフラン２２０ｍｌで再結晶して化合物８（１１．１７ｇ、８１％）を製造した。 Production Example 4: Synthesis of the following compound 8 [Compound 8]

Compound A-2 (10.00 g, 20.62 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (3 -Bromophenyl) -4,6-diphenyl-1,3,5-triazine (7.58 g, 19.59 mmol) was completely dissolved in 280 ml of tetrahydrofuran, and a 2M aqueous solution of potassium carbonate (140 ml) was added. After (triphenylphosphine) palladium (0.71 g, 0.62 mmol) was added, the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 ml of tetrahydrofuran to produce Compound 8 (11.17 g, 81%).

  MS [M + H] + = 667.

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ｉ‐２（９．００ｇ、１３．５５ｍｍｏｌ）、２‐クロロ‐４，６‐ジフェニル‐１，３，５‐トリアジン（２‐ｃｈｌｏｒｏ‐４，６‐ｄｉｐｈｅｎｙｌ‐１，３，５‐ｔｒｉａｚｉｎｅ）（３．３９ｇ、１２．６９ｍｍｏｌ）をテトラヒドロフラン２６０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１３０ｍｌ）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（０．０７ｇ、０．１３ｍｍｏｌ）を入れた後、３時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させ、テトラヒドロフラン２１０ｍｌで再結晶して化合物９（８．１７ｇ、８１％）を製造した。 Production Example 5: Synthesis of Compound 9 below [Compound 9]

Compound I-2 (9.00 g, 13.55 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl) in a 500 ml round bottom flask under a nitrogen atmosphere. After completely dissolving -1,3,5-triazine (3.39 g, 12.69 mmol) in 260 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (130 ml) was added, and tetrakis- (triphenylphosphine) palladium (0. After adding 07 g (0.13 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 210 ml of tetrahydrofuran to produce Compound 9 (8.17 g, 81%).

  MS [M + H] + = 756.

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ｉ‐２（８．００ｇ、１２．３１ｍｍｏｌ）、２‐（３‐ブロモフェニル）‐４，６‐ジフェニル‐１，３，５‐トリアジン（２‐（３‐ｂｒｏｍｏｐｈｅｎｙｌ）‐４，６‐ｄｉｐｈｅｎｙｌ‐１，３，５‐ｔｒｉａｚｉｎｅ）（４．５２ｇ、１１．６９ｍｍｏｌ）をテトラヒドロフラン２２０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１１０ｍｌ）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（０．４３ｇ、０．３７ｍｍｏｌ）を入れた後、４時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させ、テトラヒドロフラン２３０ｍｌで再結晶して化合物１０（７．４６ｇ、７３％）を製造した。 Production Example 6: Synthesis of the following compound 10 [Compound 10]

Compound I-2 (8.00 g, 12.31 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (3 -Bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.52 g, 11.69 mmol) was completely dissolved in 220 ml of tetrahydrofuran, and a 2M aqueous solution of potassium carbonate (110 ml) was added. After adding (triphenylphosphine) palladium (0.43 g, 0.37 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 ml of tetrahydrofuran to produce Compound 10 (7.46 g, 73%).

  MS [M + H] + = 832

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ｂ‐２（９．００ｇ、１８．５６ｍｍｏｌ）、２‐（３‐ブロモフェニル）‐４，６‐ジフェニル‐１，３，５‐トリアジン（２‐（３‐ｂｒｏｍｏｐｈｅｎｙｌ）‐４，６‐ｄｉｐｈｅｎｙｌ‐１，３，５‐ｔｒｉａｚｉｎｅ）（６．８２ｇ、１７．６３ｍｍｏｌ）をテトラヒドロフラン２４０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１２０ｍｌ）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（０．６４ｇ、０．５６ｍｍｏｌ）を入れた後、５時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させ、テトラヒドロフラン１７０ｍｌで再結晶して化合物１１（９．７２ｇ、７９％）を製造した。 Production Example 7: Synthesis of the following compound 11 [Compound 11]

Compound B-2 (9.00 g, 18.56 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (3 -Bromophenyl) -4,6-diphenyl-1,3,5-triazine (6.82 g, 17.63 mmol) was completely dissolved in 240 ml of tetrahydrofuran, and a 2M aqueous solution of potassium carbonate (120 ml) was added. After adding (triphenylphosphine) palladium (0.64 g, 0.56 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 170 ml of tetrahydrofuran to produce Compound 11 (9.72 g, 79%).

  MS [M + H] + = 667.

窒素雰囲気で５００ｍｌの丸底フラスコに化合物Ｂ‐２（９．００ｇ、１８．５６ｍｍｏｌ）、２‐（［１，１´‐ビフェニル］‐４‐イル）‐４‐（３‐ブロモフェニル）‐６‐フェニル‐１，３，５‐トリアジン（２‐（［１，１´‐ｂｉｐｈｅｎｙｌ］‐４‐ｙｌ）‐４‐（３‐ｂｒｏｍｏｐｈｅｎｙｌ）‐６‐ｐｈｅｎｙｌ‐１，３，５‐ｔｒｉａｚｉｎｅ）（８．１６ｇ、１７．６３ｍｍｏｌ）をテトラヒドロフラン３６０ｍｌに完全に溶解した後、２Ｍ炭酸カリウム水溶液（１８０ｍｌ）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（０．６４ｇ、０．５６ｍｍｏｌ）を入れた後、５時間加熱攪拌した。常温に温度を下げて水層を除去し、無水硫酸マグネシウムで乾燥した後、減圧濃縮させ、テトラヒドロフラン２２０ｍｌで再結晶して化合物１２（１１．２９ｇ、８２％）を製造した。 Production Example 8: Synthesis of Compound 12 below [Compound 12]

Compound B-2 (9.00 g, 18.56 mmol), 2-([1,1′-biphenyl] -4-yl) -4- (3-bromophenyl) -6 was placed in a 500 ml round bottom flask under a nitrogen atmosphere. -Phenyl-1,3,5-triazine (2-([1,1'-biphenyl) -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine) (8 .16 g, 17.63 mmol) was completely dissolved in 360 ml of tetrahydrofuran, a 2M aqueous potassium carbonate solution (180 ml) was added, and tetrakis- (triphenylphosphine) palladium (0.64 g, 0.56 mmol) was added. The mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 ml of tetrahydrofuran to produce Compound 12 (11.29 g, 82%).

  MS [M + H] + = 743

<Experimental example 1-1>
A glass substrate coated with a thin film of indium tin oxide (ITO) with a thickness of 1,000 入 れ was placed in distilled water in which a detergent was dissolved, and washed with ultrasonic waves. In this case, a detergent manufactured by Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter (Filter) manufactured by Millipore Co. was used as distilled water. After the ITO was washed for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the completion of the distilled water cleaning, the substrate was subjected to ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning device. After cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporation apparatus.

Hexazatriphenylene hexanitrile (HAT-CN) of the following chemical formula was thermally vacuum-deposited to a thickness of 500 ° on the prepared ITO transparent electrode to form a hole injection layer.
[HAT-CN]

The following compound 4-4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (NPB) (300 °), which is a substance for transporting holes, is vacuum-deposited on the hole injection layer by vacuum evaporation. A hole transport layer was formed.
[NPB]

Next, the following compound 3 was vacuum-deposited on the hole transport layer in a thickness of 100 ° to form an electron suppressing layer.
[Compound 3]

［ＢＤ］

［ＥＴ１］

［ＬｉＱ］

Subsequently, the following BH and BD were vacuum-deposited at a weight ratio of 25: 1 on the electron suppressing layer at a thickness of 300 ° to form a light emitting layer.
[BH]

[BD]

[ET1]

[LiQ]

  The compound ET1 and the compound LiQ (lithium quinolate) were vacuum-deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer with a thickness of 300 °. A negative electrode was formed on the electron injection and transport layer by sequentially depositing lithium fluoride (LiF) at a thickness of 12 ° and aluminum at a thickness of 2,000 °.

In the above process, the deposition rate of the organic material is maintained at 0.4 to 0.7 ° / sec, the negative electrode lithium fluoride is maintained at 0.3 ° / sec, and the aluminum is maintained at 2 ° / sec. The temperature was maintained at 2 × 10 ^{−7 to} 5 × 10 ⁻⁶ torr, and an organic light emitting device was manufactured.

<Experimental example 1-2>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that Compound 5 was used instead of Compound 3 in Experimental Example 1.

<Experimental example 1-3>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that Compound 6 was used instead of Compound 3 in Experimental Example 1.

<Comparative Example 1>
An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that Compound EB1 shown below was used instead of Compound 1 in Experimental Example 1.
[EB1]

<Comparative Example 2>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that Compound EB2 shown below was used instead of Compound 1 in Experimental Example 1.
[EB2]

<Comparative Example 3>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1 except that the compound of EB3 shown below was used instead of Compound 3 in Experimental Example 1.
[EB3]

When current was applied to the organic light emitting devices manufactured in Experimental Examples 1-1 to 1-3 and Comparative Examples 1 to 3, the results in Table 1 were obtained.

  As shown in Table 1, the organic light-emitting device manufactured using the compound of the present invention as an electron-suppressing layer has Comparative Examples 1 and 2 in which an amine group is linked to another position of the core of the present invention. Compared with the case of using the substance of Comparative Example 2 and the case of using the substance of Comparative Example 3 in which only the aryl group is substituted, the compound of the present invention plays a role of electron suppression, so that the efficiency of the organic light emitting device can be improved. It shows excellent characteristics in terms of driving voltage and / or stability.

  Experimental examples 1-1 to 1-3 exhibit characteristics in which the driving voltage is reduced by 10% to 12% and the efficiency is higher by 10% or more than those of Comparative examples 1 to 3.

  As shown in the results of Table 1, it was confirmed that the compound according to the present invention was excellent in electron suppressing ability and applicable to an organic light emitting device.

<Experimental examples 2-1 to 2-3>
An experiment was performed in the same manner as in Experimental Example 1-1 except that the following EB4 material was used as the electron suppressing layer and the compounds of Experimental Examples 1-1 to 1-3 were used instead of NPB as the hole transport layer.
[EB4]

<Comparative Example 3>
An organic light emitting device was manufactured in the same manner as in Experimental Example 2 except that the compound of EB1 was used instead of Compound 3 in Experimental Example 2-1.

<Comparative Example 4>
An organic light emitting device was manufactured in the same manner as in Experimental Example 2 except that the compound of EB2 was used instead of Compound 3 in Experimental Example 2-1.

When current was applied to the organic light emitting devices manufactured in Experimental Examples 2-1 to 2-3 and Comparative Examples 3 and 4, the results in Table 2 were obtained.

  As shown in Table 2, the organic light-emitting device manufactured using the compound of the present invention as a hole transport layer had Comparative Example 3 in which an amine group was linked to another position of the core of the present invention. Compared with the case where the substance of Comparative Example 4 is used, the compound of the present invention exhibits excellent properties in terms of efficiency, driving voltage and / or stability of the organic light emitting device because it plays a role of hole transport. .

  Specifically, Experimental Examples 2-1 to 2-3 show characteristics in which the drive voltage is reduced by 5% to 8% or more and the efficiency is 7 to 10% or more higher than the comparative example.

  As shown in the results of Tables 1 and 2, it was confirmed that the compound according to the present invention was excellent not only in electron suppressing ability but also in hole transporting ability and was applicable to organic light emitting devices. .

<Comparative Example 5>
After high purity sublimation purification of the compound synthesized in the above synthesis example by a generally known method, a green organic light emitting device was manufactured by the following method.

  A glass substrate coated with a thin film of indium tin oxide (ITO) with a thickness of 1,000 入 れ was placed in distilled water in which a detergent was dissolved, and washed with ultrasonic waves. In this case, a detergent manufactured by Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter (Filter) manufactured by Millipore Co. was used as distilled water. After the ITO was washed for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the completion of the distilled water cleaning, the substrate was subjected to ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning device. After cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporation apparatus.

  On the thus prepared ITO transparent electrode, using CBP as a host, m-MTDATA (60 nm) / TCTA (80 nm) / CBP + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq3 (30 nm) ) / LiF (1 nm) / Al (200 nm) in this order to produce an organic light emitting device.

The structures of m-MTDATA, TCTA, Ir (ppy) 3, CBP and BCP are as follows, respectively.

<Experimental example 3-1>
An organic light-emitting device was manufactured in the same manner as in Experimental Example 2, except that Compound 8 was used instead of CBP in Comparative Example 5.

<Experimental example 3-2>
An organic light emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 9 was used instead of Compound CBP in Comparative Example 5.

<Experimental example 3-3>
An organic light emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 10 was used instead of Compound CBP in Comparative Example 5.

<Experimental example 3-4>
An organic light emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 11 was used instead of Compound CBP in Comparative Example 5.

<Experimental example 3-5>
An organic light emitting device was manufactured in the same manner as in Comparative Example 5, except that Compound 12 was used instead of Compound CBP in Comparative Example 5.

<Comparative Example 6>
An organic light emitting device was manufactured in the same manner as in Comparative Example 5 except that the compound of GH1 shown below was used instead of the compound CBP in Comparative Example 5.
[GH1]

<Comparative Example 7>
An organic light emitting device was manufactured in the same manner as in Comparative Example 5 except that the following compound GH2 was used instead of the compound CBP in Comparative Example 5.
[GH2]

When a current was applied to the organic light-emitting devices manufactured in Comparative Example 5, Experimental Examples 3-1 to 3-5, and Comparative Examples 6 and 7, the results in Table 3 were obtained.

  As a result of the experiment, the green organic light-emitting devices of Experimental Examples 3-1 to 3-5 using the compound of the present invention as a host material of the green light-emitting layer have a structure similar to Comparative Example 5 using the conventional CBP and the core of the present invention. It was confirmed that the organic light-emitting device of the present invention exhibited better performance in terms of current efficiency and driving voltage than the organic light-emitting device manufactured using the compounds of Comparative Examples 6 and 7 as a green host material.

  The preferred embodiments (electron suppressing layer, hole transport layer, green light emitting layer) of the present invention have been described above, but the present invention is not limited to these, and the claims and the detailed description of the invention are not limited thereto. Various modifications can be made within the scope of the description, and this also belongs to the scope of the invention.

Claims (11)

A compound represented by the following chemical formula 1.
[Chemical formula 1]

In the above chemical formula 1,
R ₁ and R ₂ may be the same or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or R ₁ and R ₂ are bonded to each other. To form a substituted or unsubstituted ring;
L ₁ is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
L ₂ is an unsubstituted phenylene group,
m is an integer of 0 to 5,
n is 0 or 1,
When m is 2 or more, L ₁ may be the same or different from each other;
Ar ₁ is hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted phosphine oxide group;
Ar ₂ is a substituted arylamine group; a triazine group substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group;
R, R ′ and R ″ may be the same or different from each other, and each independently represents hydrogen; deuterium; halogen; nitrile; nitro; hydroxy; carbonyl; ester; Substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted Substituted or unsubstituted alkenyl group; substituted or unsubstituted aralkyl group; substituted or unsubstituted alkylaryl group; substituted or unsubstituted alkylamine group; substituted or unsubstituted Aralkylamine group; substituted or unsubstituted heteroarylamine group; substituted or unsubstituted arylamine group; Other unsubstituted aryl phosphine group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group
a and b may be the same or different from each other, and are each independently an integer of 0 to 4;
When a is 2 or more, R's may be the same or different from each other;
When b is 2 or more, R ″ may be the same or different from each other. The compound of claim 1, wherein the compound represented by Formula 1 is represented by Formula A or Formula B below.
[Chemical formula A]

[Chemical formula B]

In the chemical formulas A and B,
The definitions of R ₁ , R ₂ , L ₁ , L ₂ , m, n, Ar ₁ , Ar ₂ , R, R ′, R ″, a and b are the same as in Chemical Formula 1. Ar ₁ is a pyridine group substituted with at least one substituent selected from the group consisting of a phenyl group, a naphthyl group, a pyridine group, a phenyl group and a biphenyl group; a pyrimidine group; A pyrimidine group substituted with one or more selected substituents; a triazine group; a triazine group substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; a carbazole group; The compound according to claim 1, wherein the compound is a carbazole group substituted with one or more selected from the group consisting of a group and a naphthyl group. The compound according to any one of claims 1 to 3 , wherein L ₁ is a direct bond; or any one linking group selected from the following group.

Wherein R ₁ and R ₂ may be the same or different from each other, each independently, a methyl group or a phenyl group, a compound according to any one of claims 1 to 4. The compound according to claim 1, wherein the compound represented by Formula 1 is one selected from the following structures.

An organic light-emitting device including 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 the organic material layer comprises a compound according to any one of claims 1 to 6, the organic light emitting element. The organic layer can be an electron-transporting layer, an electron injection layer, and comprises more than one layer of the electron transport and electron performed injected simultaneously layers, one layer or more of said layers comprising said compounds, according to claim 7 Organic light emitting device. The organic light emitting device according to claim 7 , wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer. The organic material layer includes a hole injection layer, an electron suppression layer, a hole transport layer, and one or more layers of layers that simultaneously perform hole injection and hole transport, and one or more layers of the layers are The organic light emitting device according to claim 7 , comprising a compound. The organic light emitting device according to claim 7 , wherein the organic layer includes the compound as a host, and includes another organic compound, a metal, or a metal compound as a dopant.

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