KR102665872B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention is used in the organic material layer, preferably the light-emitting layer, of the organic electroluminescent device, thereby improving the luminous efficiency, driving voltage, and lifespan of the organic electroluminescent device. etc. can be improved.

Description

Organic compounds and organic electroluminescent devices containing the same {ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME}

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device containing the same.

Beginning with the observation of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and Tang in 1987. ) presented an organic electroluminescent device with a layered structure divided into a hole layer and a functional layer of the light-emitting layer. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

So far, hole injection layer and hole transport layer. NPB, BCP, Alq ₃ , etc. are widely known as hole blocking layer and electron transport layer materials, and anthracene derivatives are reported as light emitting layer materials. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, produce blue, green, and red colors. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and their thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

In order to solve the above problems, the purpose of the present invention is to provide a new compound that can improve the efficiency, lifespan, and stability of an organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms;

R ₁ is hydrogen, deuterium, C ₁ ~ C ₃₀ alkyl, halogen, cyano group, nitro group, hydroxy group, C ₁ ~ C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₃₀ Alkynyl group, C ₃ to C ₃₀ cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group with 5 to 30 nuclear atoms, 1 of C ₆ to C ₃₀ A non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group of C ₆ to C ₃₀ , an alkyloxy group of C ₁ to C ₃₀ , an aryloxy group of C ₆ to C ₃₀ , C ₆ to C ₃₀ an arylthio group, a C ₁ to C ₃₀ alkylamine group, a C ₆ to C ₃₀ arylamine group, a C ₁ to C ₃₀ alkylsilyl group, or a C ₅ to C ₃₀ arylsilyl group;

Ring A is a C ₆ to C ₃₀ monovalent non-aromatic condensed polycyclic group or a C ₆ to C ₃₀ monovalent non-aromatic heterocondensed polycyclic group;

The arylene group and heteroarylene group of L ₁ and L ₂ , the non-aromatic condensed polycyclic group and non-aromatic hetero condensed polycyclic group of ring A, and the alkyl, cycloalkyl, heterocycloalkyl, alkyl group, alkenyl, and alkyl group of R ₁ Nyl, aryl, heteroaryl, alkyloxy group, aryloxy group, arylthio group, alkylamine group, arylamine group, alkylsilyl group and arylsilyl group are each independently selected from deuterium, halogen, cyano group, C ₃ to C ₃₀ . Cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₃₀ alkynyl group, C ₆ to C ₃₀ aryl group, C ₆ ~ C ₃₀ monovalent non-aromatic condensed polycyclic group, C ₆ ~ C ₃₀ monovalent non-aromatic heterocondensed polycyclic group, C ₁ ~ C ₃₀ alkyloxy group, C ₆ ~ C ₃₀ aryloxy group , heteroaryl group with 5 to 30 nuclear atoms, C ₆ to C ₃₀ arylthio group, C ₁ to C ₃₀ alkylamine group, C ₆ to C ₃₀ arylamine group, C ₁ to C ₃₀ alkylsilyl. It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylsilyl group and C ₅ to C ₃₀ , and when substituted with a plurality of substituents, they may be the same or different from each other.

The present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound of Formula 1. .

In the present invention, “alkyl” is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl. etc., but is not limited to this.

In the present invention, “alkenyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 30 carbon atoms and having at least one carbon-carbon double bond, examples of which include vinyl, Examples include allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

In the present invention, “alkynyl” is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 30 carbon atoms and having at least one carbon-carbon triple bond, examples of which include ethynyl. , 2-propynyl, etc., but is not limited thereto.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 30 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and it is further interpreted to include a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, and benzothiazole; Examples include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R means aryl having 5 to 30 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, where R' means 1 to 30 alkyl, and has a linear, branched, or cyclic structure. It is interpreted as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 30 carbon atoms.

“Cycloalkyl” in the present invention refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 30 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 5 to 7 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, It is substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 30 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 5 to 30 carbon atoms.

“Condensed ring” in the present invention means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

In the present invention, a "monovalent non-aromatic condensed polycyclic group" has two or more rings condensed with each other and contains only carbon as a ring forming atom (for example, the number of carbon atoms is 8 to 60). can) and refers to a monovalent group in which the entire molecule has non-aromaticity. Examples of the non-aromatic condensed polycyclic group include a fluorenyl group and the like.

In the present invention, a "monovalent non-aromatic condensed heteropolycyclic group" refers to two or more rings condensed with each other, and carbon as a ring forming atom (for example, the number of carbon atoms is 2 to 60) refers to a monovalent group that contains heteroatoms selected from N, O, P, and S in addition to the molecule, and the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, etc.

Since the compound of the present invention has excellent thermal stability, carrier transport ability, luminescence ability, etc., it can be usefully applied as an organic layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device containing the compound of the present invention in the organic material layer has greatly improved aspects such as luminous performance, driving voltage, lifespan, and efficiency, and can be effectively applied to full color display panels.

Figure 1 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
Figure 2 shows a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

1. Novel organic compounds

The new compound of the present invention can be represented by the following formula (1):

[Formula 1]

In Formula 1,

L ₁ and L ₂ are each independently selected from the group consisting of a single bond, an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms;

R ₁ is hydrogen, deuterium, C ₁ ~ C ₃₀ alkyl, halogen, cyano group, nitro group, hydroxy group, C ₁ ~ C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₃₀ Alkynyl group, C ₃ to C ₃₀ cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group with 5 to 30 nuclear atoms, 1 of C ₆ to C ₃₀ A non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group of C ₆ to C ₃₀ , an alkyloxy group of C ₁ to C ₃₀ , an aryloxy group of C ₆ to C ₃₀ , C ₆ to C ₃₀ an arylthio group, a C ₁ to C ₃₀ alkylamine group, a C ₆ to C ₃₀ arylamine group, a C ₁ to C ₃₀ alkylsilyl group, or a C ₅ to C ₃₀ arylsilyl group;

Ring A is a C ₆ to C ₃₀ monovalent non-aromatic condensed polycyclic group or a C ₆ to C ₃₀ monovalent non-aromatic heterocondensed polycyclic group;

The arylene group and heteroarylene group of L ₁ and L ₂ , the non-aromatic condensed polycyclic group and non-aromatic hetero condensed polycyclic group of ring A, and the alkyl, cycloalkyl, heterocycloalkyl, alkyl group, alkenyl, and alkyl group of R ₁ Nyl, aryl, heteroaryl, alkyloxy group, aryloxy group, arylthio group, alkylamine group, arylamine group, alkylsilyl group and arylsilyl group are each independently selected from deuterium, halogen, cyano group, C ₃ to C ₃₀ . Cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₃₀ alkynyl group, C ₆ to C ₃₀ aryl group, C ₆ ~ C ₃₀ monovalent non-aromatic condensed polycyclic group, C ₆ ~ C ₃₀ monovalent non-aromatic heterocondensed polycyclic group, C ₁ ~ C ₃₀ alkyloxy group, C ₆ ~ C ₃₀ aryloxy group , heteroaryl group with 5 to 30 nuclear atoms, C ₆ to C ₃₀ arylthio group, C ₁ to C ₃₀ alkylamine group, C ₆ to C ₃₀ arylamine group, C ₁ to C ₃₀ alkylsilyl. It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylsilyl group and C ₅ to C ₃₀ , and when substituted with a plurality of substituents, they may be the same or different from each other.

Generally, among organic layers included in organic electroluminescent devices, the phosphorescent layer includes a host and a dopant to increase color purity and luminous efficiency. At this time, the host must have a triplet energy gap higher than that of the dopant. That is, in order to effectively provide phosphorescent light emission from a dopant, the energy of the lowest excited state of the host must be higher than the energy of the lowest emission state of the dopant.

However, in the case of the compound represented by Formula 1 provided by the present invention, the structural portion of benzo[c][1,2,5]thiadiazole has a wide singlet energy level and a high triplet energy level. Furthermore, these benzo[c][1,2,5]thiadiazoles have substituents such as phenyl, naphthalenyl, fluorene, carbazole, dibenzofuran, or dibenzothiophene, such as phenylene, biphenylene, or naphthalene. By being introduced through various linkers such as talenyl, the compound of Formula 1 can exhibit a higher energy level than the dopant when applied as a host of the light-emitting layer.

In addition, since the compound represented by Formula 1 has high triplet energy as described above, it can prevent excitons generated in the light-emitting layer from diffusing (moving) to the adjacent electron transport layer or hole transport layer. Therefore, using the compound of Formula 1, an organic material layer (hereinafter referred to as 'auxiliary light emitting layer') is formed between the hole transport layer and the light-emitting layer, or an organic material layer (hereinafter referred to as 'electron transport auxiliary layer') is formed between the light-emitting layer and the electron transport layer. ) When forming, the diffusion of excitons is prevented by the compound, so unlike conventional organic electroluminescent devices that do not include the light-emitting auxiliary layer or the electron transport auxiliary layer, the excitons that substantially contribute to light emission within the light-emitting layer By increasing the number, the luminous efficiency of the device can be improved.

Moreover, the compound represented by Formula 1 can have HOMO and LUMO energy levels adjusted depending on the substituents introduced into the basic skeleton, and thus can have a wide band gap and high carrier transport properties.

In addition, when a large electron donating group (EDG) is combined in the compound represented by Formula 1 of the present invention, it can be easily used as a hole transport layer material. In addition, when an electron withdrawing group (EWG) with high electron absorption is bonded to the basic skeleton of the compound represented by Formula 1, the entire molecule has bipolar characteristics, thereby increasing the binding force between holes and electrons. You can.

Furthermore, the compound represented by Formula 1 of the present invention significantly increases the molecular weight of the compound by introducing various substituents, especially aryl groups and/or heteroaryl groups, into the basic skeleton as described above, and thus the glass transition temperature. is improved and can have higher thermal stability than conventional organic layer materials (for example, CBP). In addition, the compound represented by Formula 1 of the present invention is also effective in suppressing crystallization of the organic layer.

As such, in the present invention, the compound represented by Formula 1 is used as an organic material layer material of an organic electroluminescent device, preferably a light-emitting layer material (blue, green and/or red phosphorescent host material), an electron transport layer/injection layer material, and a hole transport layer/ When applied as an injection layer material, a light emitting auxiliary layer material, or a lifespan improvement layer material, the performance and lifespan characteristics of an organic electroluminescent device can be greatly improved. These organic electroluminescent devices can ultimately maximize the performance of full-color organic light emitting panels.

According to a preferred embodiment of the present invention, the compound may be a compound represented by the following formula (2):

[Formula 2]

In Formula 2,

L ₁ , L ₂ , ring A and R ₁ are each as defined in Formula 1 above.

According to a preferred embodiment of the present invention, Ring A may be a substituent represented by the following Chemical Formula 3 or Chemical Formula 4:

[Formula 3]

[Formula 4]

In Formula 3 and Formula 4 above,

* refers to the part where the combination takes place;

X is C(R ₂ ) or N;

Y is selected from the group consisting of C(R ₃ )(R ₄ ), N(R ₅ ), O and S;

R ₂ to R ₅ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group with 5 to 30 nuclear atoms, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ Aryloxy group, C ₁ ~ C ₃₀ alkylsilyl group, C ₅ ~ C ₃₀ arylsilyl group, C ₁ ~ C ₃₀ alkyl boron group, C ₆ ~ C ₃₀ aryl boron group, C ₆ ~ C ₃₀ It is selected from the group consisting of an arylphosphanyl group, a C ₆ ~ C ₃₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₃₀ arylamine group, or combines with an adjacent group to form a condensed ring, preferably deuterium, selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₂ to R ₅ Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently an alkyl group, alkenyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkyl group. Silyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylamine group are each independently selected from deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ ~ C ₃₀ aryl group, number of nuclear atoms 5 to 30 heteroaryl groups, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ aryloxy group, C ₁ to C ₃₀ alkylsilyl group, C ₅ to C ₃₀ arylsilyl group, C ₁ ~C ₃₀ alkyl boron group, C ₆ ~ C ₃₀ aryl boron group, C ₆ ~ C ₃₀ arylphosphanyl group, C ₆ ~ C ₃₀ mono or diarylphosphinyl group and C ₆ ~ C ₃₀ aryl It is substituted or unsubstituted with one or more substituents selected from the group consisting of amine groups, and when substituted with a plurality of substituents, they are the same or different from each other;

Q ₁ and Q ₂ are each independently selected from the group consisting of C ₆ to C ₃₀ arenes and heteroarenes with 5 to 30 nuclear atoms;

The arene and heteroarene of Q ₁ and Q ₂ are each independently an alkyl group of C ₁ to C ₃₀ , an aryl group of C ₆ to C ₃₀ , a heteroaryl group of 5 to 30 nuclear atoms, or a monovalent non-aromatic condensed polycyclic group. It is substituted or unsubstituted with one or more substituents selected from the group consisting of monovalent non-aromatic heterocondensed polycyclic groups of C ₆ to C ₃₀ , and when substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, ring A may be a substituent represented by any one of the following formulas 5 to 8:

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

In Formulas 5 to 8,

* refers to the part where the combination takes place;

m and n are each independently integers from 0 to 4;

p is an integer from 0 to 3;

X is C(R ₂ ) or N;

Y is selected from the group consisting of C(R ₃ )(R ₄ ), N(R ₅ ), O and S;

R ₂ to R ₅ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group with 5 to 30 nuclear atoms, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ Aryloxy group, C ₁ ~ C ₃₀ alkylsilyl group, C ₅ ~ C ₃₀ arylsilyl group, C ₁ ~ C ₃₀ alkyl boron group, C ₆ ~ C ₃₀ aryl boron group, C ₆ ~ C ₃₀ It is selected from the group consisting of an arylphosphanyl group, a C ₆ ~ C ₃₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₃₀ arylamine group, or combines with an adjacent group to form a condensed ring, preferably deuterium, selected from the group consisting of a C ₁ to C ₃₀ alkyl group, a C ₆ to C ₃₀ aryl group, and a heteroaryl group having 5 to 30 nuclear atoms;

R ₆ and R ₇ are each independently deuterium, halogen, cyano group, C ₁ ~ C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , heterocycloalkyl group with 5 to 7 nuclear atoms, aryl group with C ₆ to C ₃₀ , heteroaryl group with 5 to 30 nuclear atoms, alkyloxy group with C ₁ to C ₃₀ , aryloxy with C ₆ to C _30. Period, C ₁ ~ C ₃₀ alkylsilyl group, C ₅ ~ C ₃₀ arylsilyl group, C ₁ ~ C ₃₀ alkyl boron group, C ₆ ~ C ₃₀ aryl boron group, C ₆ ~ C ₃₀ arylphos It is selected from the group consisting of a panyl group, a C ₆ ~ C ₃₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₃₀ arylamine group, or is combined with an adjacent group to form a condensed ring, preferably deuterium, C ₁ is selected from the group consisting of ~C ₃₀ alkyl group, C ₆ ~C ₃₀ aryl group, and heteroaryl group with 5 to 30 nuclear atoms, and when each of R ₆ and R ₇ is plural, they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₂ to R ₇ Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently an alkyl group, alkenyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkyl group. Silyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylamine group are each independently selected from deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ ~ C ₃₀ aryl group, number of nuclear atoms 5 to 30 heteroaryl groups, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ aryloxy group, C ₁ to C ₃₀ alkylsilyl group, C ₅ to C ₃₀ arylsilyl group, C ₁ ~C ₃₀ alkyl boron group, C ₆ ~ C ₃₀ aryl boron group, C ₆ ~ C ₃₀ arylphosphanyl group, C ₆ ~ C ₃₀ mono or diarylphosphinyl group and C ₆ ~ C ₃₀ aryl It is substituted or unsubstituted with one or more substituents selected from the group consisting of amine groups, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, ring A may be a substituent represented by any one of the following formulas A-1 to A-11:

In the above formulas A-1 to A-11,

* refers to the part where the combination takes place;

R ₃ to R ₅ are each independently hydrogen, deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ Cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group with 5 to 30 nuclear atoms, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ Aryloxy group, C ₁ ~ C ₃₀ alkylsilyl group, C ₅ ~ C ₃₀ arylsilyl group, C ₁ ~ C ₃₀ alkyl boron group, C ₆ ~ C ₃₀ aryl boron group, C ₆ ~ C ₃₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ -C ₃₀ mono or diarylphosphinyl group, and a C ₆ -C ₃₀ arylamine group, or is combined with an adjacent group to form a condensed ring;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₃ to R ₅ Boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently an alkyl group, alkenyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkyl group. Silyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylamine group are each independently selected from deuterium, halogen, cyano group, C ₁ to C ₃₀ alkyl group, C ₂ ~ C ₃₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 5 to 7 nuclear atoms, C ₆ ~ C ₃₀ aryl group, number of nuclear atoms 5 to 30 heteroaryl groups, C ₁ to C ₃₀ alkyloxy group, C ₆ to C ₃₀ aryloxy group, C ₁ to C ₃₀ alkylsilyl group, C ₅ to C ₃₀ arylsilyl group, C ₁ ~C ₃₀ alkyl boron group, C ₆ ~ C ₃₀ aryl boron group, C ₆ ~ C ₃₀ arylphosphanyl group, C ₆ ~ C ₃₀ mono or diarylphosphinyl group and C ₆ ~ C ₃₀ aryl It is substituted or unsubstituted with one or more substituents selected from the group consisting of amine groups, and when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, L ₁ and L ₂ may each be independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, and a naphthalenyl group.

According to a preferred embodiment of the present invention, R ₁ may be selected from the group consisting of hydrogen, phenyl, naphthalenyl, pyridinyl group, pyrimidinyl group, and triazinyl group.

The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

The compound of Formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 :313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ), etc.). The detailed synthesis process for the compound of the present invention will be described in detail in the synthesis examples described later.

2. Organic electric field light emitting element

Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) containing the compound represented by Formula 1 according to the above-described present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is It includes a compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of these organic material layers has the formula above. It may include a compound represented by 1.

The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, but referring to Figure 1 as an example, for example, an anode 10 and a cathode 20 facing each other, and the anode 10 and the cathode ( 20) and includes an organic layer 30 located between them. Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.

Referring to FIG. 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode. An electron injection layer 36 may be further included between (20).

In the present invention, the hole injection layer 37 laminated between the hole transport layer 31 and the anode 10 not only improves the interface characteristics between ITO used as the anode and the organic material used as the hole transport layer 31. Rather, it is a layer that is applied on top of the ITO, which has an uneven surface, and functions to smooth the surface of the ITO. It can be used without particular restrictions as long as it is commonly used in the art. For example, an amine compound can be used. It is not limited to this.

In addition, the electron injection layer 36 is a layer that is laminated on the top of the electron transport layer to facilitate electron injection from the cathode and ultimately improves power efficiency. If it is commonly used in the technical field, it is a special layer. It can be used without limitation, and for example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, BaO, etc. can be used.

In addition, although not shown in the drawings, in the present invention, a light-emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light-emitting layer 32. The light-emitting auxiliary layer may serve to transport holes to the light-emitting layer 32 and adjust the thickness of the organic layer 30. The light emitting auxiliary layer may include a hole transport material and may be made of the same material as the hole transport layer 31.

In addition, although not shown in the drawings, in the present invention, a lifespan improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes moving through the ionization potential level in the organic light-emitting device to the light-emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer and cannot diffuse or move to the electron transport layer, thereby limiting the holes to the light-emitting layer. . This function of limiting holes to the light-emitting layer prevents holes from diffusing into the electron transport layer, which moves electrons through reduction, and suppresses the phenomenon of lifespan reduction through irreversible decomposition reactions due to oxidation, contributing to improving the lifespan of organic light-emitting devices. You can.

In the present invention, the benzo[c][1,2,5]thiadiazole moiety of the compound represented by Formula 1 has excellent electrochemical stability, high glass transition temperature, and excellent carrier transport ability, Electron mobility is also very excellent, showing characteristics that increase blue light emission efficiency. In addition, the materials represented by Chemical Formula 1 are structurally characterized by bonding to the core core and an electron-withdrawing group (EWG), and have particularly excellent electron mobility, as well as a high glass transition temperature and excellent thermal stability. Therefore, it is preferable that the organic material layer containing the compound represented by Formula 1 is a light-emitting layer or a light-emitting auxiliary layer because it can greatly improve the luminous efficiency, luminance, power efficiency, thermal stability, and device lifespan of the organic electroluminescent device.

More preferably, the compound represented by Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light-emitting layer, and preferably may be a green or red phosphorescent host of the light-emitting layer.

In addition, in the present invention, the organic electroluminescent device not only includes an anode, one or more organic material layers, and a cathode sequentially stacked as described above, but may additionally include an insulating layer or an adhesive layer at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic layers (e.g., electron transport auxiliary layer) includes the compound represented by Formula 1 above. It can be manufactured by forming other organic layers and electrodes.

The organic material layer may be formed by vacuum deposition or solution application. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

There is no particular limitation on the substrate that can be used in the present invention, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.

In addition, the anode material may be made of, for example, a conductor with a high work function to facilitate hole injection, and may 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); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

In addition, the cathode material can be made of a conductor with a low work function to facilitate electron injection, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. Same metals or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al, etc., but are not limited thereto.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[ Synthesis example One] cpd synthesis of 1

<Step 1> 4- bromo -7- Phenylbenzo[c][1,2,5]thiadiazole synthesis

Compound 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), phenylboronic acid (2.4g, 20.0mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) was placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to produce compound 4-bromo-7-phenylbenzo[c][1,2,5]thiadiazole (4.7g, yield 81%). ) was obtained.

<Step 2> cpd synthesis of 1

4-Bromo-7-phenylbenzo[c][1,2,5]thiadiazole (4.7 g, 16.2 mmol) obtained in <Step 1> above in a nitrogen atmosphere in a three-neck round bottom flask heated and dried under vacuum. Dibenzo[b,d]thiophen-4-ylboronic acid (5.6 g, 19.4 mmol) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol) were added to a flask and mixed with 24.3 ml of 2M Na ₂ CO ₃ saturated aqueous solution. 100 ml of toluene was added and dissolved, followed by heating and stirring for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain compound Cpd 1 (6.5 g, yield 88%).

HRMS[M] ⁺ : 453.563

[ Synthesis example 2] cpd Composition of 2

<Step 1> 4-([1,1'-biphenyl]-4-yl)-7- Bromobenzo[c][1,2,5]thiadiazole synthesis

Compound 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), [1,1'-biphenyl]-4-ylboronic acid (3.9g, 20.0mmol) mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) were placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound 4-([1,1'-biphenyl]-4-yl)-7-bromobenzo[c][1, 2,5]thiadiazole (5.8g, yield 79%) was obtained.

<Step 2> cpd Composition of 2

The 4-([1,1'-biphenyl]-4-yl)-7-bromobenzo[c][1,2 obtained in <Step 1> above was placed in a three-neck round bottom flask heated and dried under vacuum under a nitrogen atmosphere. ,5] Thiadiazole (5.8 g, 15.8 mmol) and 9H-carbazole (3.2 g, 19.0 mmol) were dissolved in 100 ml of toluene, and then Pd ₂ (dba) ₃ (0.7 g, 0.8 mmol) was added under nitrogen. . Afterwards, NaOtBu (3 g, 31.6 mmol) was added, and (t-Bu) ₃ P (0.8 ml, 0.8 mmol) was added to the reaction solution, and the mixture was refluxed and stirred for 5 hours.

After confirming that the reaction was complete by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain compound Cpd 2 (5.9 g, yield 83%). HRMS[M] ⁺ : 456.130

[ Synthesis example 3] cpd Composition of 3

<Step 1> 4- bromo -7- Phenylbenzo[c][1,2,5]thiadiazole synthesis

Compound 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), phenylboronic acid (2.4g, 20.0mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) was placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to produce compound 4-bromo-7-phenylbenzo[c][1,2,5]thiadiazole (4.7g, yield 81%). ) was obtained.

<Step 2> cpd Composition of 3

4-Bromo-7-phenylbenzo[c][1,2,5]thiadiazole (4.7 g, 16.2 mmol) obtained in <Step 1> above in a nitrogen atmosphere in a three-neck round bottom flask heated and dried under vacuum. (3-(7H-benzo[c]carbazol-7-yl)phenyl)boronic acid (6.5 g, 19.4 mmol) and Pd(PPh ₃ ) ₄ (0.9g, 0.8 mmol) were added to the flask and dissolved in 2M Na ₂ CO ₃ 24.3 ml of saturated aqueous solution and 100 ml of toluene were added and dissolved, followed by heating and stirring for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 2 (6.7 g, yield 82%). HRMS[M] ⁺ : 503.146

[ Synthesis example 4] cpd synthesis of 4

<Step 1> 4- bromo -7- Phenylbenzo[c][1,2,5]thiadiazole synthesis

Compound 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), phenylboronic acid (2.4g, 20.0mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) was placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to produce compound 4-bromo-7-phenylbenzo[c][1,2,5]thiadiazole (4.7g, yield 81%). ) was obtained.

<Step 2> cpd Composition of 3

4-Bromo-7-phenylbenzo[c][1,2,5]thiadiazole (4.7 g, 16.2 mmol) obtained in <Step 1> above in a nitrogen atmosphere in a three-neck round bottom flask heated and dried under vacuum. 9-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-9H-carbazole (8.1 g, 19.4 mmol ) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol) were placed in a flask, dissolved in 24.3 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 100 ml of Touene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 4 (7 g, yield 86%). HRMS[M] ⁺ : 503.146

[ Synthesis example 5] cpd synthesis of 5

<Step 1> 4- bromo -7- (naphthalen-2-yl)benzo[c][1,2,5]thiadiazole synthesis

Compounds 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), naphthalen-2-ylboronic acid (3.4g, 20.0mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) was placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to produce compound 4-bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole ( 5.8g, yield 85%) was obtained.

<Step 2> cpd synthesis of 5

4-Bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole (4.8) obtained in <Step 1> above in a nitrogen atmosphere in a three-neck round bottom flask heated and dried under vacuum. g, 17.0 mmol), dibenzo[b,d]furan-2-ylboronic acid (4.3 g, 20.4 mmol) and Pd(PPh ₃ ) ₄ (0.9g, 0.8 mmol) were added to the flask and 2M Na ₂ CO ₃ 25.5 ml of saturated aqueous solution and 100 ml of toluene were added and dissolved, followed by heating and stirring for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 5 (6.3 g, yield 87%). HRMS[M] ⁺ : 428.098

[ Synthesis example 6] cpd synthesis of 6

<Step 1> 4- bromo -7- (naphthalen-2-yl)benzo[c][1,2,5]thiadiazole synthesis

Compounds 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), naphthalen-2-ylboronic acid (3.4g, 20.0mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) was placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to produce compound 4-bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole ( 5.8g, yield 85%) was obtained.

<Step 2> cpd synthesis of 6

4-Bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole (4.8) obtained in <Step 1> above in a nitrogen atmosphere in a three-neck round bottom flask heated and dried under vacuum. g, 17.0 mmol), dibenzo[b,d]thiophen-2-ylboronic acid (4.6 g, 20.4 mmol) and Pd(PPh ₃ ) ₄ (0.9g, 0.8 mmol) were added to the flask and 2M Na ₂ CO ₃ 25.5 ml of saturated aqueous solution and 100 ml of toluene were added and dissolved, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 6 (6.7 g, yield 89%). HRMS[M] ⁺ : 444.075

[ Synthesis example 7] cpd Composition of 7

<Step 1> 4- bromo -7- (naphthalen-2-yl)benzo[c][1,2,5]thiadiazole synthesis

Compounds 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), naphthalen-2-ylboronic acid (3.4g, 20.0mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) was placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to produce compound 4-bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole ( 5.8g, yield 85%) was obtained.

<Step 2> cpd Composition of 7

4-Bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole (4.8) obtained in <Step 1> above in a nitrogen atmosphere in a three-neck round bottom flask heated and dried under vacuum. g, 17.0 mmol), (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (4.8 g, 20.4 mmol) and Pd(PPh ₃ ) ₄ (0.9g, 0.8 mmol) were added to the flask and 2M 25.5 ml of saturated Na ₂ CO ₃ aqueous solution and 100 ml of toluene were added and dissolved, followed by heating and stirring for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain compound Cpd 7 (6.8 g, yield 89%). HRMS[M] ⁺ : 454.150

[ Synthesis example 8] cpd Composition of 8

<Step 1> 4- bromo -7- (naphthalen-2-yl)benzo[c][1,2,5]thiadiazole synthesis

Compounds 4,7-dibromobenzo[c][1,2,5]thiadiazole (5.9g, 20.0mmol), naphthalen-2-ylboronic acid (3.4g, 20.0mmol) and Pd(PPh ₃ ) ₄ (1.1 g, 1.0 mmol) was placed in a flask, dissolved in 30 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 200 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to produce compound 4-bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole ( 5.8g, yield 85%) was obtained.

<Step 2> cpd Composition of 8

4-Bromo-7-(naphthalen-2-yl)benzo[c][1,2,5]thiadiazole (4.8) obtained in <Step 1> above in a nitrogen atmosphere in a three-neck round bottom flask heated and dried under vacuum. g, 17.0 mmol), 7-phenyl-10-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-7H-benzo[c]carbazole ( 8.5 g, 20.4 mmol) and Pd(PPh ₃ ) ₄ (0.9 g, 0.8 mmol) were placed in a flask, dissolved in 25.5 ml of 2M Na ₂ CO ₃ saturated aqueous solution and 100 ml of toluene, and then heated and stirred for 8 hours.

After completion of the reaction, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 8 (7.7 g, yield 82%). HRMS[M] ⁺ : 553.161

[ Example 1~28] Red organic electric field Manufacturing of light emitting devices

The compound Cpd1 synthesized in Synthesis Example 1 was purified to high purity by sublimation using a commonly known method, and then a red organic electroluminescent device was manufactured as follows.

First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate using UV for 5 minutes and using a vacuum evaporator. The substrate was transferred to .

On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/compound of the synthesis example + 10% (piq) ₂ Ir(acac) (30nm)/BCP (10 nm)/Alq ₃ (30 nm) An organic electroluminescent device was manufactured by stacking /LiF (1 nm)/Al (200 nm) in that order.

The structures of m-MTDATA, TCTA, (piq) ₂ Ir(acac), CBP and BCP used herein are as follows.

[ Comparative example One]

A red organic electroluminescent device was manufactured in the same process as Example 1, except that CBP was used instead of Cpd1, the compound synthesized in Synthesis Example 1, as a light-emitting host material when forming the light-emitting layer.

Here, the structures of m-MTDATA, TCTA, (piq) ₂ Ir(acac), CBP and BCP used are as follows.

[ Evaluation example One]

The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each organic electroluminescent device manufactured in Examples 1 to 28 and Comparative Example 1, and the results are shown in Table 2 below.

Sample host driving voltage
(V) Current efficiency
(cd/A) Example 1 Cpd 1 4.90 10.2 Example 2 Cpd 2 4.82 11.0 Example 3 Cpd 3 4.80 12.8 Example 4 Cpd 4 4.59 12.0 Example 5 Cpd 5 4.65 10.4 Example 6 Cpd 6 4.92 9.4 Example 7 Cpd 7 4.87 9.8 Example 8 Cpd 8 4.90 11.5 Example 9 Cpd 9 4.59 10.2 Example 10 Cpd 10 4.65 10.8 Example 11 Cpd 11 4.92 10.4 Example 12 Cpd 12 4.87 12.1 Example 13 Cpd 13 4.90 9.8 Example 14 Cpd 14 4.90 11.5 Example 15 Cpd 15 4.82 10.2 Example 16 Cpd 16 4.80 10.2 Example 17 Cpd 17 4.59 11.0 Example 18 Cpd 18 4.65 12.8 Example 19 Cpd 19 4.92 12.0 Example 20 Cpd 20 4.87 10.4 Example 21 Cpd 21 4.90 9.4 Example 22 Cpd 22 4.87 9.8 Example 23 Cpd 23 4.90 11.5 Example 24 Cpd 24 4.77 10.2 Example 25 Cpd 25 4.92 10.8 Example 26 Cpd 26 4.87 10.4 Example 27 Cpd 27 4.90 12.1 Example 28 Cpd 28 4.92 10.4 Comparative Example 1 CBP 5.25 8.2

As shown in Table 1, when the compound according to the present invention was used as a material for the light-emitting layer of a red organic electroluminescent device (Examples 1 to 28), a red organic electroluminescent device using conventional CBP as a material for the light-emitting layer (Comparative Example) Compared to 1), it can be seen that it shows excellent performance in terms of efficiency and driving voltage.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto and can be implemented with various modifications within the scope of the claims and detailed description of the invention, which also fall within the scope of the invention. It is natural.

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transport auxiliary layer
34: electron transport layer 35: electron transport auxiliary layer
36: electron injection layer 37: hole injection layer

Claims (10)

Compound represented by the following formula (2):
[Formula 2]

In Formula 2,
L ₁ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;
L2 is selected from the group consisting of a single bond and a heteroarylene group having 5 to 18 nuclear atoms;
R1 is hydrogen, a C1~C30 alkyl group, or a C6~C30 monovalent aromatic heterocondensed polycyclic group;
Ring A is an aromatic heterocondensed polycyclic group;
Ring A is a substituent represented by any one of the following formulas A-2 and A-5 to A-11;

In the above formulas A-2 and A-5 to A-11,
* refers to the part where the combination takes place;
R3 to R5 are each independently hydrogen, deuterium, halogen, cyano group, C1 to C30 alkyl group, C2 to C30 alkenyl group, C2 to C40 alkynyl group, C3 to C40 cycloalkyl group, and 5 to 5 nuclear atoms. 7 heterocycloalkyl groups, aryl group of C6~C30, heteroaryl group of 5~30 nuclear atoms, alkyloxy group of C1~C30, aryloxy group of C6~C30, alkylsilyl group of C1~C30, C5~ C30 aryl silyl group, C1 to C30 alkyl boron group, C6 to C30 aryl boron group, C6 to C30 arylphosphanyl group, C6 to C30 mono or diarylphosphinyl group and C6 to C30 arylamine group. is selected from the group consisting of, or is combined with an adjacent group to form a condensed ring;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, and aryl boron group of R3 to R5. , arylphosphanyl group, mono or diarylphosphinyl group, and arylsilyl group are each independently an alkyl group, alkenyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, and alkylsilyl group. , arylsilyl group, alkylborone group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group, and arylamine group are each independently selected from deuterium, halogen, cyano group, alkyl group of C1~C30, and C2~C30 of Alkenyl group, alkynyl group of C2 to C40, cycloalkyl group of C3 to C40, heterocycloalkyl group of 5 to 7 nuclear atoms, aryl group of C6 to C30, heteroaryl group of 5 to 30 nuclear atoms, C1 to C30 Alkyloxy group, C6~C30 aryloxy group, C1~C30 alkylsilyl group, C5~C30 arylsilyl group, C1~C30 alkyl boron group, C6~C30 aryl boron group, C6~C30 arylphos It is substituted or unsubstituted with one or more substituents selected from the group consisting of panyl group, C6~C30 mono or diarylphosphinyl group, and C6~C30 arylamine group, and when substituted with multiple substituents, they are the same or different from each other. You can;
The arylene group _and heteroarylene group of L ₁ and L ₂ , the aromatic condensed polycyclic group and aromatic condensed heteropolycyclic group of ring A, and the alkyl, cycloalkyl, heterocycloalkyl, alkyl group, alkenyl, alkynyl, Aryl, heteroaryl, alkyloxy group, aryloxy group, arylthio group, alkylamine group, arylamine group, alkylsilyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, and C ₃ to C ₃₀ cycloalkyl group. , heterocycloalkyl group with 5 to 7 nuclear atoms, C ₁ to C ₃₀ alkyl group, C ₂ to C ₃₀ alkenyl group, C ₂ to C ₃₀ alkynyl group, C ₆ to C ₃₀ aryl group, C ₆ to C ₃₀ monovalent non-aromatic condensed polycyclic group, C ₆ ~ C ₃₀ monovalent non-aromatic heterocondensed polycyclic group, C ₁ ~ C ₃₀ alkyloxy group, C ₆ ~ C ₃₀ aryloxy group, nucleus Heteroaryl group having 5 to 30 atoms, C ₆ to C ₃₀ arylthio group, C ₁ to C ₃₀ alkylamine group, C ₆ to C ₃₀ arylamine group, C ₁ to C ₃₀ alkylsilyl group, and It is substituted or unsubstituted with one or more substituents selected from the group consisting of C ₅ to C ₃₀ arylsilyl groups, and when substituted with multiple substituents, they may be the same or different from each other.
delete delete delete delete delete delete According to paragraph 1,
The compound represented by Formula 2 is characterized in that it is selected from the group consisting of the following compounds:
An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode,
An organic electroluminescent device, wherein at least one of the one or more organic layers includes the compound represented by the formula (2) of claim 1. According to clause 9,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a lifespan improvement layer, a light emitting layer, and a light emitting auxiliary layer.