KR20170057729A - Nitrile based compound and organic light emitting device comprising the same - Google Patents

Nitrile based compound and organic light emitting device comprising the same Download PDF

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KR20170057729A
KR20170057729A KR1020150161234A KR20150161234A KR20170057729A KR 20170057729 A KR20170057729 A KR 20170057729A KR 1020150161234 A KR1020150161234 A KR 1020150161234A KR 20150161234 A KR20150161234 A KR 20150161234A KR 20170057729 A KR20170057729 A KR 20170057729A
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홍완표
김형철
김연환
김동헌
윤준
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주식회사 엘지화학
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    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
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    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract

Provided are a nitrile-based compound represented by chemical formula 1 or chemical formula 2, and an organic light-emitting device including the same. According to the present invention, the compound can be used as a material for organic layers in organic light-emitting devices.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrile compound and an organic light emitting device including the compound. [0002]

TECHNICAL FIELD The present invention relates to a nitrile-based compound and an organic light emitting device including the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

Korean Patent Publication No. 2000-0051826

In this specification, nitrile-based compounds and organic light emitting devices containing them are described.

An embodiment of the present disclosure provides a compound represented by the following formula 1 or 2:

[Chemical Formula 1]

Figure pat00001

In formula (1), R1a to R4a are the same or different from each other and represent hydrogen; A halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted three or more ring aromatic rings bonded to adjacent groups; Or a substituted or unsubstituted three or more ring heterocyclic ring,

X1 and X2 are the same or different and are each independently hydrogen or a halogen group,

(2)

Figure pat00002

In Formula 2,

R1b to R4b are the same or different from each other and represent hydrogen; A halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring,

X3 is hydrogen or a halogen group.

In addition, one embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, light emitting, electron transporting, charge generating or electron injecting materials. In addition, the compounds described in the present specification can be preferably used as a light emitting layer, an electron transporting or electron injecting material. More preferably, the compounds described herein exhibit low voltage, high efficiency, and / or long life characteristics when used as a material for hole injection, hole transport, charge generation, and electron blocking layer.

1 illustrates an example of an organic light emitting device including a substrate 100, a cathode 110, a light emitting layer 150, and a cathode 120. FIG.
2 shows an example of an organic light emitting device comprising a substrate 100, an anode 110, a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160 and a cathode 120 It is.
3 illustrates an anode 110, a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer 160. An electron injection layer 170, and a cathode 120. The organic light emitting device shown in FIG.
Figure 4 shows an anode 210; A first hole injection layer 231, a first hole transport layer 241, and a first light emitting layer 251. A first stack S-1 made up of a first electron transport layer 261 and a first electron injection layer 271; A first hole injection layer 232, a first hole transport layer 242, and a first light emitting layer 252. A second stack S-2 made up of a first electron transport layer 262 and a first electron injection layer 272; A charge generation layer 280 provided between the first stack S-1 and the second stack S-2 and including an N-type charge generation layer 280N and a P-type charge generation layer 280P; And an anode 220. The organic light emitting device shown in FIG.
Figures 5 and 6 are 1 H NMR spectra of compounds according to the present invention.

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

One embodiment of the present invention provides a compound represented by the above formula (1) or (2).

The compound represented by the above formula (1) or (2) is an acene compound or a derivative thereof having at least four or more nitrile groups arranged symmetrically and has a high electron affinity value and thus is highly stable in electron acceptance. Further, since the structure has condensed three or more aromatic rings, it can be refined into a high purity substance with excellent heat resistance, and an appropriate deposition temperature can be maintained. Thus, an organic light emitting device can be manufactured by a vapor deposition method. when the acene compound or its derivative is applied to a hole injection layer and a charge generation layer, particularly as a material for an organic light emitting device, the driving voltage of the organic light emitting device can be lowered and the lifetime can be realized.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term "substituted or unsubstituted" A nitrile group; A carbonyl group; An ester group; Haloalkyl; An alkylsulfonyl group; Arylsulfonyl group; Aralkyl groups; An alkylaryl group; An aryl group; A haloaryl group; Or a heterocyclic group, or a substituted or unsubstituted group substituted with at least two of the above-exemplified substituents. For example, the group to which the two substituents are connected is an aryl group substituted with a haloalkyl; An aryl group substituted with a nitrile group; An aryl group substituted with an aryl group or a heterocyclic group; A heterocyclic group substituted with an aryl group or a heterocyclic group, and the like.

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

In the present specification, the haloalkyl group is an alkyl group substituted with a halogen group. The haloalkyl 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 in the haloalkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group in the haloalkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group in the haloalkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group in the haloalkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- Propyl, n-pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, Butyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, Dimethylheptyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

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 phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, a fluorenyl group and a triphenylene group.

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

When the fluorenyl group is substituted,

Figure pat00003
,
Figure pat00004
,
Figure pat00005
,
Figure pat00006
,
Figure pat00007
,
Figure pat00008
,
Figure pat00009
And
Figure pat00010
And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinolyl group, a quinolyl group, a quinolyl group, an imidazolyl group, , A quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, , Benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofurane group, phenanthroline, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group , A phenoxazinyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group.

In the present specification, an alkylsulfonyl group and an arylsulfonyl group may be represented by -SO 2 R, wherein R is an alkyl group or an aryl group.

In the present specification, a carbonyl group may be represented by -C (= O) R, wherein R is an alkyl group or an aryl group.

In the present specification, the ester group may be represented by -COOR, wherein R is an alkyl group or an aryl group.

In the present specification, the aryl group in the arylsulfonyl group, the aralkyl group, the alkylaryl group, the haloaryl group, the carbonyl group and the ester group can be applied to the description of the aryl group described above.

In the present specification, the description of the alkyl group contained in the above-mentioned haloalkyl group can be applied to the alkylsulfonyl group, aralkyl group, alkylaryl group, carbonyl group, and ester group.

In this specification, the term " forming a ring by bonding to adjacent groups " means bonding to adjacent groups to form a substituted or unsubstituted aliphatic ring or a substituted or unsubstituted aromatic ring. An unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; Or a condensed ring thereof.

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

Specific examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. But are not limited to these.

In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. In the present specification, specifically, examples of the aromatic hydrocarbon ring include phenyl, naphthyl, anthracenyl, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, But are not limited to, cyclopentene, cyclopentene, cyclopentene, cyclopentene, cyclopentene, cyclopentene, cyclohexene,

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom. Specific examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, Azokane, thiocane, and the like, but are not limited thereto.

As used herein, an aromatic heterocyclic ring means an aromatic ring containing at least one heteroatom. 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, quinoline, quinazoline, quinoxaline, naphthyridine And examples thereof include at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of at least one selected from the group consisting of pyridine, But are not limited to, furan, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, phenanthroline, indolocarbazole, no.

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

Examples of the aromatic ring having three or more rings include phenanthrene, acenaphthylene, phenanthridine, phenanthroline, pyrazinoquinoxaline, benzodithiophene and the like.

According to one embodiment of the present invention, R1a to R4a in Formula 1 are the same or different from each other, and at least one of R1a to R4a is a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted three or more ring aromatic rings bonded to adjacent groups; Or a substituted or unsubstituted three or more ring heterocycle.

According to one embodiment of the present invention, R1a to R4a in the general formula (1) are the same as or different from each other, and represent a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted three or more ring aromatic rings bonded to adjacent groups; Or a substituted or unsubstituted three or more ring heterocycle.

According to one embodiment of the present invention, R1a to R4a in Formula 1 are the same or different from each other, and at least one of R1a to R4a is a halogen group; A nitrile group; A carbonyl group; An ester group; Haloalkyl; An alkylsulfonyl group; Arylsulfonyl group; An aryl group substituted or unsubstituted with a nitrile group; A haloaryl group; Or a heterocyclic group, or three or more aromatic rings substituted with an adjacent group to form a substituted or unsubstituted group with a halogen or nitrile group; Or a substituted or unsubstituted three or more ring heterocycle.

According to one embodiment of the present invention, R1a to R4a in the general formula (1) are the same or different from each other and represent a fluoro group; A chloro group; A nitrile group; A carbonyl group; An ester group; Fluoromethyl group; A fluoroethyl group; A methylsulfonyl group; A phenyl group substituted or unsubstituted with a nitrile group; A fluorophenyl group; Fluoromethylphenyl group; Thiophene group; A phenanthroline ring substituted with a halogen group or a nitrile group to form a phenanthroline ring; A pyrazinoquinoxaline ring substituted or unsubstituted with a halogen group or a nitrile group; An acenaphthylene ring substituted or unsubstituted with a halogen group or a nitrile group; Or a benzodithiophene ring substituted or unsubstituted with a halogen group or a nitrile group.

According to one embodiment of the present invention, R1a and R2a in Formula 1 are hydrogen, and at least one of R3a and R4a is a fluoro group; A chloro group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted fluoromethyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted methylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted fluoromethylphenyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted fluorophenyl group; A substituted or unsubstituted thiophene group; Or a substituted or unsubstituted pyridine group, or a substituted or unsubstituted phenanthrene ring in which R3a and R4a are bonded to each other; A substituted or unsubstituted phenanthroline ring; A substituted or unsubstituted pyrazinoquinoxaline ring; A substituted or unsubstituted acenaphthylene ring; Or a substituted or unsubstituted benzodithiophene ring.

In another embodiment, R1a and R2a in the above formula (1) are substituted or unsubstituted haloaryl groups, and R3a and R4a are bonded to each other to form a substituted or unsubstituted three-ring or more ring. Specifically, R1a and R2a in the formula (1) are phenyl groups substituted or unsubstituted with a fluoro group, R3a and R4a are bonded to each other to form a substituted or unsubstituted phenanthrene ring; Or a substituted or unsubstituted phenanthroline ring.

In another embodiment, R1a and R2a in the above formula (1) are bonded to each other to form a substituted or unsubstituted ring of three or more rings, and R3a and R4a are bonded to each other to form a substituted or unsubstituted tricyclic ring do. Specifically, R 1 a and R 2 a in Formula 1 may be bonded to each other to form a substituted or unsubstituted phenanthroline ring, and R 3 a and R 4 a may bond to each other to form a substituted or unsubstituted phenanthrene ring.

According to one embodiment of the present invention, R1a to R4a in the formula (1) are bonded to adjacent groups to form a substituted or unsubstituted three-ring or more aromatic ring; Or a substituted or unsubstituted tricyclic heterocyclic ring, the formula (1) may be represented by the following formulas (11) to (17).

(11)

Figure pat00011

[Chemical Formula 12]

Figure pat00012

[Chemical Formula 13]

Figure pat00013

[Chemical Formula 14]

Figure pat00014

[Chemical Formula 15]

Figure pat00015

[Chemical Formula 16]

Figure pat00016

[Chemical Formula 17]

Figure pat00017

In formulas (11) to (17), X 1 and X 2 have the same definitions as in formula (1), R and R 'are the same or different from each other and represent hydrogen; A halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; P and q are each an integer of 0 to 8, r, s, t and u are integers of 0 to 6, m and n are each an integer of 0 to 4, When p, q, r, s, t, u, m and n are each 2 or more, the substituents in the parentheses are the same or different.

According to one embodiment of the present invention, R1b to R4b in the formula (2) are the same or different from each other, and at least one of R1b to R4b is a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R1b to R4b in the general formula (2) are the same or different and each independently represents a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R1b to R4b in the general formula (2) are the same or different and each independently represents a halogen group; A nitrile group; A carbonyl group; An ester group; Haloalkyl; An alkylsulfonyl group; Arylsulfonyl group; An aryl group substituted or unsubstituted with a nitrile group; A haloaryl group; Or a heterocyclic group or a monocyclic or polycyclic aromatic ring which is bonded to adjacent groups to be substituted or unsubstituted with a halogen group or a nitrile group; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R1b to R4b in the above formula (2) are the same or different from each other and each independently represents a fluoro group; A chloro group; A nitrile group; A carbonyl group; An ester group; Fluoromethyl group; A fluoroethyl group; A methylsulfonyl group; A phenyl group substituted or unsubstituted with a nitrile group; A fluorophenyl group; Fluoromethylphenyl group; Thiophene group; Or a pyridine group or a benzene ring which is bonded to adjacent groups to be substituted or unsubstituted with a halogen group or a nitrile group; A phenanthrene ring substituted or unsubstituted with a halogen group or a nitrile group; A phenanthroline ring substituted or unsubstituted with a halogen group or a nitrile group; A pyrazinoquinoxaline ring substituted or unsubstituted with a halogen group or a nitrile group; An acenaphthylene ring substituted or unsubstituted with a halogen group or a nitrile group; Or a benzodithiophene ring substituted or unsubstituted with a halogen group or a nitrile group.

According to one embodiment of the present invention, R 1b to R 4b in formula (2) are bonded to adjacent groups to form a substituted or unsubstituted three-ring or more aromatic ring; Or a substituted or unsubstituted three or more ring heterocyclic ring, the formula (2) may be represented by the following formulas (21) to (27).

[Chemical Formula 21]

Figure pat00018

[Chemical Formula 22]

Figure pat00019

(23)

Figure pat00020

≪ EMI ID =

Figure pat00021

(25)

Figure pat00022

(26)

Figure pat00023

(27)

Figure pat00024

In Formulas 21 to 27, the definition of X3 is the same as in Formula 2, R and R 'are the same or different from each other and represent hydrogen; A halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; P and q are each an integer of 0 to 8, r, s, t and u are integers of 0 to 6, m and n are each an integer of 0 to 4, When p, q, r, s, t, u, m and n are each 2 or more, the substituents in the parentheses are the same or different.

According to one embodiment of the present invention, R1b and R2b in the above formula (2) are hydrogen.

According to one embodiment of the present invention, R1b and R2b in Formula 2 are hydrogen, and at least one of R3b and R4b is a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R1b and R2b in the formula (2) are hydrogen, and at least one of R3b and R4b is a fluoro group; A chloro group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted fluoromethyl group; A substituted or unsubstituted fluoroalkyl group; A substituted or unsubstituted methylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted fluoromethylphenyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted fluorophenyl group; A substituted or unsubstituted thiophene group; Or a substituted or unsubstituted pyridine group, or a substituted or unsubstituted phenanthrene ring bonded to adjacent groups; A substituted or unsubstituted phenanthroline ring; A substituted or unsubstituted pyrazinoquinoxaline ring; A substituted or unsubstituted acenaphthylene ring; Or a substituted or unsubstituted benzodithiophene ring.

According to one embodiment of the present invention, R1b and R2b in the general formula (2) are hydrogen, R3b and R4b are the same or different, and represent a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R1b and R2b in the general formula (2) are hydrogen, R3b and R4b are the same or different, and represent a halogen group; A nitrile group; A carbonyl group; An ester group; Haloalkyl; An alkylsulfonyl group; Arylsulfonyl group; An aryl group substituted or unsubstituted with a nitrile group; A haloaryl group; Or a heterocyclic group or a monocyclic or polycyclic aromatic ring which is bonded to adjacent groups to be substituted or unsubstituted with a halogen group or a nitrile group; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

In another embodiment, R1b and R2b in the general formula (1) are substituted or unsubstituted haloaryl groups, R3b and R4b are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic ring, monocyclic or polycyclic hetero To form a ring. Specifically, R1b and R2b in the formula (1) are phenyl groups substituted or unsubstituted with a fluoro group, R3b and R4b are bonded to each other to form a substituted or unsubstituted phenanthrene ring; Or a substituted or unsubstituted phenanthroline ring.

According to one embodiment of the present invention, R 1b and R 2b in Formula 2 are bonded to adjacent groups to form a substituted or unsubstituted aromatic ring; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R1b and R2b in formula (2) are bonded to each other to form a substituted or unsubstituted aromatic ring.

According to one embodiment of the present invention, R 1b and R 2b in Formula 2 are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, R 1b and R 2b in Formula 2 are bonded to each other to form a substituted or unsubstituted phenanthrene ring.

According to one embodiment of the present invention, R1b and R2b in formula (2) are bonded to each other to form a benzene ring.

According to one embodiment of the present invention, R 1b and R 2b in Formula 2 are bonded to each other to form a phenanthrene ring. According to one embodiment of the present invention, Or an unsubstituted aromatic ring; Or a substituted or unsubstituted heterocycle, and at least one of R3b and R4b is a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R 1b and R 2b in the general formula (2) are bonded to adjacent groups to form a substituted or unsubstituted aromatic ring; Or a substituted or unsubstituted heterocyclic ring, R3b and R4b are the same or different and are a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

According to one embodiment of the present invention, R 1b and R 2b in the general formula (2) are bonded to adjacent groups to form a substituted or unsubstituted aromatic ring; Or a substituted or unsubstituted heterocyclic ring, R3b and R4b are the same or different and are a halogen group; A nitrile group; A carbonyl group; An ester group; Haloalkyl; An alkylsulfonyl group; Arylsulfonyl group; An aryl group substituted or unsubstituted with a nitrile group; A haloaryl group; Or a heterocyclic group or a monocyclic or polycyclic aromatic ring which is bonded to adjacent groups to be substituted or unsubstituted with a halogen group or a nitrile group; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring.

In another embodiment, R 1b and R 2b in the above formula (1) are a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to each other; Or a substituted or unsubstituted monocyclic or polycyclic aromatic ring which is substituted or unsubstituted when R3b and R4b are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring; Or a substituted or unsubstituted monocyclic or polycyclic ring. Specifically, R 1b and R 2b in formula (1) may bond to each other to form a substituted or unsubstituted phenanthroline ring, and R 3b and R 4b may bond to each other to form a substituted or unsubstituted phenanthrene ring.

According to one embodiment, R, R 'and R " are each hydrogen; A halogen group; A nitrile group; A carbonyl group; An ester group; Haloalkyl; An alkylsulfonyl group; Arylsulfonyl group; An aryl group substituted or unsubstituted with a nitrile group; A haloaryl group; Or a heterocyclic group.

In one embodiment of the present invention, R, R 'and R " are each hydrogen; A fluoro group; A chloro group; A nitrile group; A carbonyl group; Fluoromethyl group; A fluoroethyl group; Or a methylsulfonyl group.

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

In one embodiment of the present invention, X1 is hydrogen and X2 is a fluoro group.

In one embodiment of the present invention, X1 is a fluoro group and X2 is hydrogen.

In one embodiment of the present invention, X1 and X2 are fluoro groups.

In one embodiment of the present invention, X3 is hydrogen.

In one embodiment of the present invention, X3 is a fluoro group.

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

Figure pat00025

Figure pat00026

Figure pat00027

Figure pat00028

Figure pat00029

Figure pat00030

Figure pat00031

Figure pat00032

According to one embodiment of the present invention, the compound of Formula 2 may be any one selected from the following compounds.

Figure pat00033

Figure pat00034

Figure pat00035

Figure pat00036

Figure pat00037

According to one embodiment, the compounds of formulas (1) and (2) described above can be prepared according to the following reaction scheme.

The benzene tetraacetonitrile derivatives of the present invention can be prepared by methods known in the literature, for example, in Journal of the Chemical Society, Perkin Transactions 1 (1983) 1443, or Bulletin of the Chemical Society of Japan (2010) Can be synthesized by the following Reaction Scheme 1 with reference to the synthesis method.

[Reaction Scheme 1]

Figure pat00038

Also, with reference to <Inorganic Chemistry> (2005) Vol. 44, No. 7970, the derivatives shown in the following Reaction Scheme 2 can be synthesized.

[Reaction Scheme 2]

Figure pat00039

Also, the present invention provides an organic light emitting device comprising the compound represented by the above formula (1) or (2).

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 or Formula 2 do.

The organic layer of the organic light emitting device may have a single layer structure, but may have a multi-layer 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, (1) or (2).

In another embodiment, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of the above formula (1) or (2).

In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1) or (2).

In one embodiment of the present invention, the organic layer includes an electron inhibition layer, and the electron inhibition layer includes the compound of the above formula (1) or (2).

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and electron injecting includes the compound of the above formula (1) or (2).

In another embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes the compound of the above formula (1) or (2).

The organic material layer may include two or more light emitting layers, and may include a charge generating layer including the compound of Formula 1 provided between the two light emitting layers, wherein the charge generating layer is represented by Formula 1 &Lt; / RTI &gt; compounds.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; Wherein at least one of the two or more organic layers includes at least one compound selected from the group consisting of compounds represented by the formulas (1) and (2) . In one embodiment, the two or more organic layers may be selected from the group consisting of an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and an electron injecting layer, and a hole blocking layer.

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the compound of the above formula (1) or (2). Specifically, in one embodiment of the present invention, the compound of Formula 1 or 2 may be contained in one of the two or more electron transporting layers, or may be included in each of two or more electron transporting layers.

In one embodiment of the present invention, when the compound of Formula 1 or 2 is contained in each of the two or more electron transporting layers, the materials other than the compound of Formula 1 or 2 may be the same or different from each other have.

An organic light emitting device according to an embodiment of the present invention includes a first electrode; A second electrode facing the first electrode; And a plurality of stacks provided between the first electrode and the second electrode, wherein the plurality of stacks include at least a first stack and a second stack, Emitting layer, the second stack comprising a second light emitting layer, and a charge generating layer provided between the first stack and the second stack, the charge generating layer comprising a compound of Formula 1 or Formula 2 .

In one embodiment, the charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer, and the P-type charge generation layer may comprise the compound.

In another embodiment, the first stack includes at least one organic material layer disposed between the anode and the first light emitting layer, wherein the organic material layer includes at least one of a first hole injection layer and a first hole transport layer .

In one embodiment, the P-type charge generation layer may be made of only the organic compound, or may be made of the host material and the organic compound.

In another embodiment, the first stack comprises a first hole transport layer, and the P-type antibiotic layer comprises only the compound or comprises a host material and the compound.

In one embodiment, the organic layer includes a first hole injection layer, and the first hole injection layer is made of only the compound.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, the compound may be included in the light emitting layer.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

An organic light emitting device according to an embodiment of the present invention includes an anode 110, a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, an electron injecting layer 170, 120). The anode 110 may be any one of indium tin oxide (ITO), indium zinc oxide (IZO), and zinc oxide (ZnO). When the anode 110 is a reflective electrode, the anode 110 may be formed of a reflective layer made of any one of aluminum (Al), silver (Ag), and nickel (Ni) under the layer made of any one of ITO, IZO, As shown in FIG.

In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

In another embodiment, the first electrode is a cathode and the second electrode is a cathode.

The anode 110 is an electrode for injecting holes. As the anode material, a material having a large work function is preferably used to facilitate injection of holes into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline. When the anode 110 is a reflective electrode, the anode 110 may have a reflective layer made of any one of aluminum (Al), silver (Ag), and nickel (Ni) under the layer made of any one of ITO, IZO, .

The hole injection layer 130 may function to smoothly inject holes from the anode 110 into the light emitting layer 150. The hole injection layer 130 of the present embodiment may include the compound of Formula 1 or Formula 2. The materials mentioned in the claims of the present specification are derivatives in which an anthracene or an acridine structure is a main skeleton and substituted with a nitrile group, so that they are excellent in electron accepting ability, so that power consumption can be improved and the driving voltage can be lowered.

The thickness of the hole injection layer 130 may be 1 to 150 nm. If the thickness of the hole injection layer 130 is greater than 1 nm, the hole injection characteristics can be prevented from being degraded. If the thickness is less than 150 nm, the thickness of the hole injection layer 130 is too thick, There is an advantage that it is possible to prevent the drive voltage from rising. The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect on the anode, an excellent hole injecting effect on the light emitting layer or the light emitting material due to its ability to transport holes, A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include organic materials such as metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene- Based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer 140 receives holes from the hole injection layer and transports holes to the light emitting layer. The hole transport layer 140 transports holes from the anode or the hole injection layer, A material having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

In one embodiment, the hole transport layer comprises at least one compound selected from the group consisting of NPD (N, N-dinaphthyl-N, N'-diphenylbenzidine), TPD ) -benzidine, s-TAD and MTDATA (4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenylamino) -triphenylamine). For example, a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative and a pyrazolone derivative, a phenylene diamine derivative, an arylamine derivative, an amino substituted chalcone derivative, Styryl anthracene derivatives, fluorene derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane series, aniline series copolymers, and conductive polymer oligomers (particularly thiophenol oligomers).

The light emitting layer 150 may emit red (R), green (G), or blue (B) light, and may be formed of a phosphor or a fluorescent material. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but the present invention is not limited thereto. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and ferriflantene having an arylamine group. Examples of the styrylamine compound include substituted or unsubstituted Substituted arylamine in which at least one aryl vinyl group is substituted, wherein at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. When the light emitting layer 150 is red, carbazole biphenyl (CBP) or 1,3-bis (carbazol-9-yl) benzophenone is used as the metal complex, (1-phenylisoquinoline) acetylacetonate iridium), PQIr (acac) bis (1-phenylquinoline) acetylacetonate iridium, PQIr (tris (1-phenylquinoline) iridium) and (DBM) 3 (Phen) or perylene. The phosphorescent material may be a phosphorescent material containing a dopant including at least one selected from the group consisting of PtOEP (octaethylporphyrin platinum) But are not limited thereto.

A phosphorescent material including a dopant material including Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium), which contains a host material including CBP or mCP when the light emitting layer 150 is green Alternatively, it may be made of a fluorescent material including Alq 3 (tris (8-hydroxyquinolino) aluminum), but is not limited thereto.

(4,6-F 2 ppy) 2 Irpic when the light emitting layer 150 is blue, and a phosphorescent material including a host material including CBP or mCP and containing a dopant material including (4,6-F 2 ppy) 2 Irpic, but is not limited to, a fluorescent material including any one selected from the group consisting of spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO polymer, and PPV polymer Do not.

The electron transporting layer 160 serves to smooth the transport of electrons. The electron transporting material is a layer that transports electrons to the light emitting layer by receiving electrons from the electron injection layer. As the electron transporting material, A material having high mobility to electrons is suitable as the material capable of transferring to the light emitting layer. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. In the present invention, the electron transport layer may include at least one selected from the group consisting of Alq 3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq and SAlq.

The thickness of the electron transport layer 160 may be 1 to 50 nm. Here, when the thickness of the electron transporting layer 160 is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered. When the thickness is 50 nm or less, the thickness of the electron transporting layer 160 is too thick, There is an advantage that the driving voltage can be prevented from rising.

The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer 170 is a layer for injecting electrons from the electrode. The electron injection layer 170 has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, Is prevented from migrating to the hole injection layer, and the thin film forming ability is excellent. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto. In one embodiment, the electron injecting layer may be Alq 3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq or SAlq.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, this is not limited. in addition, an electron injection layer 170 may be formed of a metal compound, a metal compound, for example LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF 2, MgF 2, CaF 2, SrF 2, BaF 2 and RaF 2 It is at least one selected from the group consisting of, but not limited to these.

The thickness of the electron injection layer 170 may be 1 to 50 nm. If the thickness of the electron injection layer 170 is 1 nm or more, there is an advantage that the electron injection characteristics can be prevented from deteriorating. If the thickness is 50 nm or less, the thickness of the electron injection layer 170 is too thick, There is an advantage that it is possible to prevent the drive voltage from rising.

The cathode 120 is an electron injection electrode, and is preferably made of a material having a small work function so as to facilitate injection of electrons 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; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto. Here, when the organic light emitting device is a front or both-side light emitting structure, the cathode 120 may be formed to have a thickness thin enough to transmit light, and when the organic light emitting device is a back light emitting structure, As shown in FIG.

4, the organic light emitting diode according to an embodiment of the present invention includes stacks S-1 and S-2 and stacks S-1 and S-2 positioned between an anode 210 and a cathode 220, And a charge generating layer 280 located between the charge generating layer 280 and the charge generating layer 280 (S-2). Although two stacks are shown between the anode 210 and the cathode 220 in the present embodiment, the present invention is not limited thereto and may include three, four, or more Stacks.

More specifically, the first stack S-1 is a unit of one light emitting device and includes a first light emitting layer 251. The first light emitting layer 251 may emit light of any one of red, green, and blue. In this embodiment, the first light emitting layer 251 may be a blue light emitting layer that emits blue light. The first stack S-1 further includes a hole injection layer 231 and a first hole transport layer 241 between the anode 210 and the first emission layer 251. The hole injection layer 231 may function to facilitate the injection of holes from the anode 210 to the first light emitting layer 251 and may be formed of cupper phthalocyanine (CuPc), poly (3,4) -ethylenedioxythiophene (PEDOT) , PANI (polyaniline) and NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine).

The first hole transport layer 241 has the same structure as the hole transport layer 140 described above. The first stack S-1 further includes a first electron transport layer 261 on the first light emitting layer 251. The first electron transport layer 261 has the same structure as the electron transport layer 261 described above. Accordingly, the first stack S-1 including the hole injection layer 220, the first hole transport layer 241, the first light emitting layer 251, and the first electron transport layer 261 is formed on the anode 210 do.

A charge generation layer (CGL) 280 is disposed on the first stack S-1. The charge generation layer 280 may be a PN junction charge generation layer in which the N-type charge generation layer 280N and the P-type charge generation layer 280P are bonded. At this time, the PN junction charge generation layer 280 generates charges or separates them into holes and electrons, and injects charges into the respective light emitting layers. That is, the N-type charge generation layer 280N supplies electrons to the first light emitting layer 251 adjacent to the anode, and the P-type charge generation layer 280P supplies holes to the light emitting layer of the second stack S- Thus, the luminous efficiency of the organic light emitting device having a plurality of light emitting layers can be further increased, and the driving voltage can be lowered.

Here, the P-type charge generation layer 280P is made of an organic compound represented by the above-described Formula 1 or Formula 2. The organic compound used for the P-type charge generation layer 280P is advantageous in that it can provide an organic light emitting device capable of improving the power efficiency, improving the power consumption, and lowering the driving voltage by having an excellent electron storage capacity.

The N-type charge generation layer 280N may be formed of an organic material doped with a metal or an N-type. The metal may be one selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy and Yb. The N-type dopant used for the organic material doped with the N-type material and the host material may be a commonly used material. For example, the N-type dopant may be an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound. In detail, the N-type dopant may be selected from the group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu and Yb. The host material may be a material selected from the group consisting of tris (8-hydroxyquinoline) aluminum, triazine, hydroxyquinoline derivatives, and benzazole derivatives and silole derivatives.

On the other hand, a second stack S-2 including a second light emitting layer 252 is positioned on the charge generating layer 280. [ The second light emitting layer 252 may emit one of red, green, and blue colors. For example, the second light emitting layer 252 may be a yellow light emitting layer that emits yellow light in this embodiment. The second light emitting layer 252 may have a multilayer structure of a light emitting layer for emitting yellow green or a light emitting layer for emitting green light. In this embodiment, a single layer structure of a yellow light emitting layer for emitting yellow green is described as an example. The second light emitting layer 290 may be formed of CBP (4,4'-N, N'-dicarbazolebiphenyl) or Balq (Bis (2-methyl-8-quinlinolato-N1, O8) - (1,1'-Biphenyl- ) aluminum). The phosphorescent yellow green dopant may emit yellow green.

The second stack S-2 further includes a second hole transport layer 242 between the charge generation layer 280 and the second emission layer 252. The second hole transport layer 242 has the same structure as the first hole transport layer 242 described above. In one embodiment, the second stack S-2 may further include an electron blocking layer between the second hole transport layer 242 and the second emission layer 252. The electron blocking layer includes a material of the hole transporting layer and a metal or a metal compound to prevent electrons generated in the light emitting layer from passing over the hole transporting layer. Therefore, the LUMO level of the electron blocking layer becomes high, and electrons can not pass over.

The second stack S-2 further includes a second electron transporting layer 262 on the second light emitting layer 252 and the second electron transporting layer 262 is formed on the first stack S- And has the same structure as the first electron transporting layer 160. Thus, the second stack S-2 including the second hole transport layer 242, the second light emitting layer 252, and the second electron transport layer 262 is formed on the charge generation layer 280, And may further include an electron blocking layer between the second light emitting layer 252 and the transport layer 242. A cathode 220 is provided on the second stack S-2 to constitute an organic light emitting diode according to the second embodiment of the present invention.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1) or (2).

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

 The organic luminescent device of the present invention can be produced by materials and methods known in the art except that at least one layer of the organic material layer contains the compound of the above formula 1 or 2, that is, the compound represented by the above formula .

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal oxide or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the organic material layer, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 or 2 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

&Lt; Preparation Example A &

Synthesis of intermediate A

Figure pat00040

Under nitrogen, 18 g of 1,2,4,5-tetrakis (bromomethyl) benzene and 3.5 g of tetraethylammonium bromide were dissolved in 600 ml of dimethylformamide and cooled to -40 ° C. Next, 9.0 g of sodium cyanide (NaCN) was dissolved in 100 ml of distilled water under a nitrogen atmosphere and slowly dropped at -40 ° C. After stirring for 2 hours, the temperature was slowly raised to -5 ° C. Thereafter, the mixture was separated into distilled water and ethyl acetate, dried over anhydrous sodium sulfate and filtered. Thereafter, the ethyl acetate was distilled off under reduced pressure, and the residue was separated and purified by alumina to obtain 8.0 g of intermediate A. The obtained solid DMSO-d6 NMR showed a peak at 7.58 ppm (s, 2H) and 4.15 ppm (s, 8H).

Synthesis of Compound A-1

Figure pat00041

4 g of 9,10-phenanthrene dione was dissolved in dimethylformamide and 1.1 g of Intermediate A was added thereto. Next, 2.2 g of sodium methoxide was dissolved in 80 ml of methanol, and the temperature was raised to 50 ° C, followed by stirring for 24 hours. Next, after cooling to room temperature, the resulting solid was filtered, washed with methanol and ethyl acetate, and dried to obtain 2.2 g. A peak was observed at M / Z = 579 by mass spectrum measurement of the obtained solid.

Synthesis of Compound A-2

Figure pat00042

In the synthesis of Compound A-1, 2.4 g of a solid was obtained by carrying out the same reaction and purification except that 4 g of 9,10-phenanthrene dione was changed to 4.0 g of phenanthrolindione ion. A peak was confirmed at M / Z = 583 by mass spectrum measurement of the obtained solid.

Synthesis of Compound A-3

Figure pat00043

Figure pat00044

In the synthesis of Compound A-1, the same reaction and purification were carried out except that 4 g of 9,10-phenanthrene dione was changed to 7.0 g of dibromo-phenanthrolindione, and 4.4 g of a solid was obtained . Next, 3.4 g of copper cyanide (CuCN) was added to 4.4 g of the powder obtained above under argon, and N-methyl-2-pyrrolidinone (200 mL) was added thereto and stirred. Thereafter, the mixture was heated to 180 ° C and stirred for 24 hours. After cooling to room temperature, ammonia water (200 mL) was added and stirred, and crystals formed were collected by filtration. The filtrate was reslurried twice with 100 mL of water, and then reslurried with 100 mL of ethanol. The obtained crystals were dried under reduced pressure using a vacuum drier to obtain 4.2 g of a powder. Peak was confirmed at M / Z = 679 by mass spectrum measurement of the obtained solid.

Synthesis of Compound A-4

Figure pat00045

Figure pat00046

Except that 4 g of 9,10-phenanthrene dione was changed to 12.0 g of 1,2-bis (4-bromophenyl) ethane-dione in the synthesis of Compound A-1 The reaction and purification were carried out to obtain 4.8 g of a solid.

Next, 4.0 g of copper cyanide (CuCN) was added to 4.8 g of the powder obtained above under argon, and N-methyl-2-pyrrolidinone (200 mL) was added thereto and stirred. Thereafter, the mixture was heated to 180 ° C and stirred for 24 hours. After cooling to room temperature, ammonia water (200 mL) was added and stirred, and crystals formed were collected by filtration. The filtrate was reslurried twice with 100 mL of water, and then reslurried with 100 mL of ethanol. The obtained crystals were dried under reduced pressure using a vacuum drier to obtain 4.8 g of powder. A peak was confirmed at M / Z = 683 by mass spectrum measurement of the obtained solid.

Synthesis of Compound A-5

Figure pat00047

Except that 4 g of 9,10-phenanthrene dione was changed to 8.4 g of 1,2-bis (4-fluorophenyl) ethane-dione in the synthesis of Compound A-5 The reaction and purification were carried out to obtain 6.8 g of a solid. A peak was confirmed at M / Z = 655 by mass spectrum measurement of the obtained solid.

&Lt; Production Example B &

Synthesis of intermediate B

Figure pat00048

Under nitrogen, 6 g of pyridine-2,3,5,6-tetrayltetramethanol was dissolved in 600 ml of chloroform, 68 ml of tribromophosphine was diluted in 600 ml of chloroform and slowly added dropwise. Then, after stirring for 24 hours under reflux, the mixture was cooled to room temperature. Next, extraction with a saturated aqueous sodium hydrogen carbonate solution and chloroform, followed by drying the obtained organic layer over anhydrous sodium sulfate (MgSO 4). After filtration, the solvent was distilled off under reduced pressure. Next, silica gel column chromatography was conducted to obtain 3.06 g of 2,3,5,6-tetrakis (bromomethyl) pyridine.

Under nitrogen, 3.0 g of 2,3,5,6-tetrakis (bromomethyl) pyridine and 0.58 g of tetraethylammonium bromide were dissolved in 120 ml of dimethylformamide and then cooled to -40 ° C. Next, 1.46 g of sodium cyanide (NaCN) was dissolved in 12 ml of distilled water under a nitrogen atmosphere and slowly dropped at -40 ° C. After stirring for 2 hours, the temperature was slowly raised to -5 ° C. Thereafter, the mixture was separated into distilled water and ethyl acetate, dried over anhydrous sodium sulfate and filtered. Thereafter, the ethyl acetate was distilled off under reduced pressure, and the residue was separated and purified by alumina to obtain 1.8 g of intermediate B. A peak was confirmed at M / Z = 236 by mass spectrum measurement of the obtained solid.

Synthesis of Compound A-6

Figure pat00049

4 g of 9,10-phenanthroline dione was dissolved in dimethylformamide and 1.1 g of Intermediate B was added thereto. Next, 2.2 g of sodium methoxide was dissolved in 80 ml of methanol, and the temperature was raised to 50 ° C, followed by stirring for 24 hours. Next, after cooling to room temperature, the resulting solid was filtered, washed with methanol and ethyl acetate, and dried to obtain 1.8 g. A peak was confirmed at M / Z = 580 by mass spectrum measurement of the obtained solid.

&Lt; Example 1-1 >

Figure pat00050

Figure pat00051

The ITO glass was patterned to have a light emitting area of 3 mm x 3 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 -6 torr. Then, α-NPD was formed to a thickness of 100 Å as a hole injecting layer on the ITO anode. Compound A-1 was doped with a doping concentration of 25% was, that the the BD-a dopant as a hole transport layer to form an α-NPD to a thickness of 600Å, and a host for the light emitting layer MADN weight ratio of 40: and deposited such that the two, to form a Alq 3 as the electron transport layer to a thickness of 300Å LiF was formed to a thickness of 10 angstroms as an electron injection layer, and Al was formed to a thickness of 800 angstroms as a cathode, thereby preparing an organic light emitting device.

&Lt; Example 1-2 >

An organic light emitting device was fabricated under the same process conditions as in Example 1-1 except that Compound A-2 was doped into the hole injection layer.

&Lt; Example 1-3 >

An organic light emitting device was fabricated under the same process conditions as in Example 1-1 except that Compound A-3 was doped into the hole injection layer.

&Lt; Example 1-4 >

An organic light emitting device was fabricated under the same process conditions as in the above-described Example 1-1 except that the compound A-4 was doped into the hole injection layer.

&Lt; Example 1-5 >

An organic light emitting device was fabricated under the same process conditions as in Example 1-1 except that Compound A-5 was doped into the hole injection layer.

&Lt; Example 1-6 >

An organic light emitting device was fabricated under the same process conditions as in Example 1-1 except that Compound A-6 was doped in the hole injection layer.

&Lt; Comparative Example 1-1 >

An organic light emitting device was fabricated under the same process conditions as in Example 1-1 except that HAT-CN was doped in the hole injection layer.

Figure pat00052

&Lt; Comparative Example 1-2 >

An organic light emitting device was fabricated under the same process conditions as in Example 1-1 except that the hole injection layer was formed without any doping.

&Lt; Comparative Example 1-3 >

An organic light emitting device was fabricated under the same process conditions as in Example 1-1 except that the hole injection layer was doped with the following compound HI 1. The following compounds were synthesized by the method described in Journal of the Chemical Society, Perkin Transcation 1 (1983), page 1443.

[HI 1]

Figure pat00053

&Lt; Comparative Example 1-4 >

An organic light emitting device was fabricated under the same process conditions as in Example 1 except that the hole injection layer was doped with the following compound HI 2.

[HI 2]

Figure pat00054

For the organic luminescent devices manufactured according to Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-4, luminance was measured using Minolta's CS1000, and the luminous efficiency at 10 mA / cm 2 And the results are shown in Table 1 below.

Hole injection layer The driving voltage (V) Current density (mA / cm 2 ) Current efficiency
(cd / A) Power Efficiency (Im / W) Luminance
(cd / m 2 ) Example 1-1 Compound A-1 4.6 10 5.5 3.756 550 Examples 1-2 Compound A-2 4.4 10 5.6 3.998 560 Example 1-3 Compound A-3 4.4 10 5.64 4.027 564 Examples 1-4 Compound A-4 5 10 5.32 3.343 532 Examples 1-5 Compound A-5 5.1 10 5.22 3.216 522 Examples 1-6 Compound A-6 4.2 10 5.78 4.323 578 Comparative Example 1-1 HAT-CN 5.8 10 4.6 2.492 460 Comparative Example 1-2 No doping 10 10 4.06 1.275 406 Comparative Example 1-3 HI 1 9 10 4.1 1.431 410 Comparative Example 1-4 HI 2 7.4 10 4.22 1.792 422

As shown in Table 1, in the case of the organic light emitting device prepared by doping the compound of the present invention into the hole injection layer, Comparative Example 1-1 using the conventional HAT-CN and Comparative Example 1-1 in which the hole injection layer was not doped -2 &gt; in terms of efficiency, driving voltage and / or stability of an organic light emitting device. In addition, low driving voltage and high current efficiency, power efficiency and brightness are shown in comparison with Comparative Examples 1-3 and 1-4 having a core structure similar to the compound according to the present invention.

As shown in Table 1, it was confirmed that the compounds according to the present invention are excellent in hole injection ability and applicable to organic light emitting devices.

&Lt; Example 2-1 >

Figure pat00055

The ITO glass was patterned to have a light emitting area of 3 mm x 3 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the base material was made to have a pressure of 1 x 10 -6 torr. Then, an organic material was formed on the ITO anode as a hole injecting layer to a thickness of 40 Å, and α-NPD was formed as a hole transporting layer Doped Ir (ppy) 3 with a doping concentration of 10% to form a 300 Å thick hole blocking layer, a 50 Å thick BCP as a hole blocking layer, and electron Alq 3 was formed to a thickness of 150 Å as a transport layer, LiF was formed to a thickness of 5 Å as an electron injection layer, and Al was sequentially formed to a thickness of 1000 Å to form a cathode.

&Lt; Example 2-2 >

An organic light emitting device was fabricated under the same process conditions as in Example 2-1 except that Compound A-2 was used in the hole injection layer.

&Lt; Example 2-3 >

An organic light emitting device was fabricated under the same process conditions as in Example 2-1 except that Compound A-4 was used in the hole injection layer.

<Example 2-4>

An organic light emitting device was fabricated under the same process conditions as in Example 2-1 except that Compound A-6 was used in the hole injection layer.

&Lt; Comparative Example 2-1 >

An organic light emitting device was fabricated under the same process conditions as in Example 2-1 except that HAT-CN was used for the hole injection layer.

&Lt; Comparative Example 2-2 &

An organic light emitting device was fabricated under the same process conditions as in Example 2-1 except that the hole injection layer was formed without any doping.

&Lt; Comparative Example 2-3 >

An organic light emitting device was fabricated under the same process conditions as in Example 2-1 except that the following compound HI 1 was used in the hole injection layer. The following compounds were synthesized by the method described in Journal of the Chemical Society, Perkin Transcation 1 (1983), page 1443.

[HI 1]

Figure pat00056

&Lt; Comparative Example 2-4 &

An organic light emitting device was fabricated under the same process conditions as in Example 2-1 except that the hole injection layer was doped with the following compound HI 2.

Figure pat00057

For the organic luminescent devices manufactured according to Examples 2-1 to 2-4 and Comparative Examples 2-1 to 2-4, the luminance was measured using CS1000 manufactured by Minolta, and the luminous efficiency at 10 mA / cm 2 And the results are shown in Table 2 below.

Hole injection layer The driving voltage (V) Current density (mA / cm 2 ) Current efficiency
(cd / A) Power Efficiency (Im / W) Luminance
(cd / m 2 ) Example 2-1 Compound A-1 4.6 10 57.88 39.529 5788 Example 2-2 Compound A-2 4.3 10 60.98 44.552 6098 Example 2-3 Compound A-4 4.4 10 58.32 41.640 5832 Examples 2-4 Compound A-6 4.2 10 62 46.376 6200 Comparative Example 2-1 HAT-CN 6 10 50.38 26.379 5038 Comparative Example 2-2 No doping 8.6 10 43.34 15.832 4334 Comparative Example 2-3 HI 1 8 10 44 17.279 4400 Comparative Example 2-4 HI 2 7.8 10 44.88 18.076 4488

As shown in Table 2, in the case of the organic light emitting device prepared by doping the compound of the present invention into the hole injection layer, Comparative Example 2-1 using the conventional HAT-CN and Comparative Example 2 -2 &gt; in terms of efficiency, driving voltage and / or stability of an organic light emitting device. In addition, low driving voltage and high current efficiency, power efficiency and brightness are shown in comparison with Comparative Examples 2-3 and 2-4 having a core structure similar to the compound according to the present invention.

As shown in Table 2, it was confirmed that the compounds according to the present invention are excellent in hole injecting ability and applicable to organic light emitting devices.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

100: substrate
110: anode
120: cathode
130: Hole injection layer
140: hole transport layer
150: light emitting layer
160: electron transport layer
170: electron injection layer
210: anode
220: cathode
231: First hole injection layer
232: second hole injection layer
241: First hole transport layer
242: second hole transport layer
251: First light emitting layer
252: second light emitting layer
261: First electron transport layer
262: Second electron transport layer
271: first electron injection layer
272: second electron injection layer
280: charge generation layer
280N: N-type charge generation layer
280P: P-type charge generation layer
S-1: First stack
S-2: Second stack

Claims (21)

A compound of the formula 1 or 2:
[Chemical Formula 1]
Figure pat00058

In formula (1), R1a to R4a are the same or different from each other and represent hydrogen; A halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted three or more ring aromatic rings bonded to adjacent groups; Or a substituted or unsubstituted three or more ring heterocyclic ring,
X1 and X2 are the same or different and are each independently hydrogen or a halogen group,
(2)
Figure pat00059

In Formula 2,
R1b to R4b are the same or different from each other and represent hydrogen; A halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring,
X3 is hydrogen or a halogen group. [4] The compound according to claim 1, wherein R1a to R4a in Formula 1 are the same or different from each other, and at least one of R1a to R4a is a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted three or more ring aromatic rings bonded to adjacent groups; Or a substituted or unsubstituted three or more ring heterocycle. [4] The compound according to claim 1, wherein R1a to R4a in the general formula (1) are the same or different from each other and each independently represents a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted three or more ring aromatic rings bonded to adjacent groups; Or a substituted or unsubstituted three or more ring heterocycle. [2] The compound according to claim 1, wherein R1b and R2b are the same or different from each other, and at least one of R1b and R2b is a nitrile group; A halogen group; Haloalkyl; A haloaryl group; Or an aryl group substituted with a haloalkyl group or a nitrile group. [2] The compound according to claim 1, wherein at least one of R3b and R4b in Formula 2 is a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring. [2] The compound according to claim 1, wherein R3b and R4b in the general formula (2) are the same or different from each other, A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring. [2] The compound according to claim 1, wherein R1a and R2a in the general formula (1) are hydrogen, R3a and R4a are the same or different and each independently represents a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted three or more ring aromatic rings bonded to adjacent groups; Or a substituted or unsubstituted three or more ring heterocycle. [3] The compound according to claim 1, wherein R1b and R2b in the general formula (1) are hydrogen, R3b and R4b are the same or different and each independently represents a halogen group; A nitrile group; A carbonyl group; An ester group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted haloaryl group; Or a substituted or unsubstituted heterocyclic group or a monocyclic or polycyclic aromatic ring substituted or unsubstituted by bonding to adjacent groups; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring. The compound of claim 1, wherein the compound of formula (1) is selected from the following formulas:
Figure pat00060

Figure pat00061

Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

Figure pat00067
. 2. The compound according to claim 1, wherein the compound of formula 2 is selected from the following formulas:
Figure pat00068

Figure pat00069

Figure pat00070

Figure pat00071

Figure pat00072
. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 10 Organic light emitting device. 12. The organic light emitting device according to claim 11, wherein the organic material layer includes a hole transporting layer, and the hole transporting layer comprises the compound. 12. The organic electroluminescent device according to claim 11, wherein the organic compound layer comprises a hole injection layer, and the hole injection layer comprises the compound. 12. The organic light emitting device according to claim 11, wherein the organic layer includes an electron suppressing layer, and the electron suppressing layer comprises the compound. [Claim 12] The organic light emitting device according to claim 11, wherein the organic layer includes a layer that simultaneously injects holes and transports holes, and the layer that simultaneously injects holes and transports the compound. A first electrode; A second electrode facing the first electrode; And a plurality of stacks provided between the first electrode and the second electrode, the plurality of stacks including at least a first stack and a second stack,
Wherein the first stack comprises a first light emitting layer,
Wherein the second stack comprises a second light emitting layer,
And a charge generation layer provided between the first stack and the second stack,
Wherein the charge generation layer comprises the compound according to any one of claims 1 to 10. 17. The organic electroluminescent device according to claim 16, wherein the charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer, and the P-type charge generation layer comprises the compound. The organic electroluminescent device of claim 16, wherein the first stack includes at least one organic material layer positioned between the anode and the first light emitting layer, wherein the organic material layer includes at least one of a first hole injection layer and a first hole transport layer Wherein the organic light-emitting device comprises: 17. The organic electroluminescent device according to claim 16, wherein the P-type charge generation layer is made of only the organic compound or is made of a host material and the organic compound. 17. The organic electroluminescent device according to claim 16, wherein the first stack includes a first hole transporting layer, and the P-type biostatic layer comprises only the compound or comprises a host material and the compound. [Claim 16] The organic light emitting device of claim 16, wherein the organic layer includes a first hole injection layer, and the first hole injection layer comprises only the compound.
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CN115028627B (en) * 2022-06-16 2023-07-07 复旦大学 Tetracyano-substituted acenaphthoquinone imide organic material and preparation method and application thereof

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