KR20140026783A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent diode including: a newly structured light emitting compound which is excellent in luminous capacity, positive hole transporting capacity, and electron transporting capacity; and one of the above compounds into an organic compound layer, so as to improve the luminance efficiency, driving voltage, and lifespan. The present invention is a chemical compound represented in chemical formula 1 below. ′Chemical Formula 1′ The chemical compound represented in the above chemical formula 1 is a compound chosen from the below chemical formula 2 through chemical formula 4. ′Chemical Formula 2′ ′Chemical Formula 3′ ′Chemical Formula 4′ In the above chemical formula, Ra stands for a C6-C40 aryl group, a heteroaryl group having the number of nuclear atoms ranging from 5 through 40, or NR3R4.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel organic light emitting compound having excellent light emitting ability, hole transporting ability, and electron transporting ability, An organic electroluminescent device having improved characteristics such as efficiency, driving voltage, and lifetime.

An organic electroluminescent device (hereinafter referred to as an organic EL device) generally has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic EL device, for example, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) ), An electron injection layer (EIL), and the like.

When a voltage is applied between the two electrodes of the organic EL device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When falling, the light comes out.

The light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. In addition, in order to increase luminous efficiency through increasing color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In general, a phosphorescent host material is a carbazole-based compound such as 4,4-dicarbazolylbiphenyl (CBP), and a phosphorescent dopant is a metal complex compound containing heavy atoms such as Ir and Pt .

However, CBP, which is a phosphorescent host material currently used, has a low glass transition temperature (T _g ) of about 110 ° C. and easily crystallizes in the device, resulting in a very short lifetime of the organic EL device to about 150 hours.

SUMMARY OF THE INVENTION The present invention has been devised to solve the problems described above, and it is an object of the present invention to provide an organic light emitting compound and an organic EL device using the same, which can improve characteristics such as luminous efficiency, driving voltage, thermal stability and lifetime.

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

Where

X and Y are the same or different and are each independently N or CH;

R ₁ and R ₂ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, -NR ₃ R ₄ , a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, and a substituted or unsubstituted 3 to 40 Or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with a group adjacent to the condensed aliphatic ring, condensed aromatic ring, condensed heteroaromatic ring or condensed heteroaromatic ring,

Wherein R ₃ and R ₄ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 40 atoms, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, and a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, or a group selected from the group consisting of A condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring,

R ₅ is H, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms heteroaryl of 5 to 40, a substituted or unsubstituted C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy of, -NR _a R _b, a substituted or unsubstituted selected from the group consisting of a cycloalkyl group of C ₃ ~ C ₄₀ unsubstituted and substituted or unsubstituted heteroaryl number of 3 to 40 nuclear atoms or a cycloalkyl group, or they A group forming a condensed aliphatic ring, a condensed aromatic ring, a condensed hetero aliphatic ring or a condensed heteroaromatic ring,

Wherein R _a and R _b are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C of ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted in the ring C ₆ ~ C ₄₀ aryl A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group and a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, or groups adjacent thereto may be bonded to each other to form a condensed aliphatic ring , Condensed aromatic rings, condensed heteroaliphatic rings or condensed heteroaromatic rings.

The present invention also provides an organic EL device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode, And a compound represented by the following general formula (1): < EMI ID = 1.0 >

In this case, the organic compound layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, and a light emitting layer. Specifically, the compound represented by Formula 1 may be used as a phosphorescent host of a light emitting layer.

The compound represented by the formula (1) of the present invention has excellent luminous ability, electron transport ability and hole transport ability. Therefore, the organic EL device including the same may greatly improve characteristics such as light emission performance, driving voltage, and lifetime, and thus may be effectively applied to a full color display panel.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel organic electroluminescent compound according to the present invention has a structure represented by the above formula (1) in which various substituents, particularly N-containing heterocyclic rings, aromatic rings, and the like, are connected to the parent moiety of the quinazoline system. Through such a structure, it is possible to attain a sufficiently high triplet energy level to improve the phosphorescence characteristic and at the same time to achieve an improved effect in electron and / or hole transporting ability, luminous efficiency, driving voltage, have.

In the compound represented by the formula (1) according to the present invention, X and Y are the same or different and each independently N or CH. In one example, Y is N, X is CH, or Y is CH and X is N. Also, both X and Y may be CH or N. [

Wherein R ₁ and R ₂ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ alkynyl group, for C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, -NR ₃ R _4, C of ₃ ~ C ₄₀ cycloalkyl An alkyl group and a heterocycloalkyl group having 3 to 40 nuclear atoms; Or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring by bonding with the adjacent groups.

Wherein R ₃ and R ₄ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₃ to C selected from the group consisting of cycloalkyl group and ₄₀ nuclear atoms, 3 to 40 or a heterocycloalkyl group of; Or a group in which they form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring adjacent to each other.

R ₅ are the same or different and each independently represents H, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, -NR _a R _b , a C ₃ to C ₄₀ cycloalkyl group, Or a heterocycloalkyl group having 1 to 40 carbon atoms, or a group in which they are bonded to each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring.

Wherein R _a and R _b are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, and a C ₃ to C ₄₀ hetero A cycloalkyl group, or they may be bonded to each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

Meanwhile, in the present formula I, in which R ₁ ~ substituent, the term "substituted or unsubstituted" described R _5, R _a, R _b, more specifically, the R ₁ ~ R _5, R _a, R _b, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C cycloalkyl group and nuclear atoms, 3 to heterocycloalkyl group of 40 of the ₄₀ are each independently selected from deuterium, halogen, cyano group, C ₁ ~ C ₄₀ the alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, an aryloxy group of a heteroaryl group of C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to _40, C ₆ ~ C 40 of the , A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ ~ C ₄₀ alkylsilyl group, and C ₆ ~ C ₄₀ aryl group consisting of silyl Or a salt thereof may be substituted.

In the compound represented by the formula (1) according to the present invention, when considering the triplet energy level, R ₁ and R ₂ are the same or different and each independently represents a C ₆ to C ₄₀ aryl group, A heteroaryl group having 5 to 40 carbon atoms, -NR ₃ R ₄ , or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring by bonding these adjacent groups to adjacent groups. Wherein R ₁ and R ₂ are most preferably in the case where the more preferable, and NR ₃ R ₄ when the respective C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, or an NR ₃ of R _4.

Here, the C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, R _3, R ₄ are each independently a heavy hydrogen, a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ of aryloxy C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of, C ₁ ~ C ₄₀ A C ₆ to C ₄₀ arylamine group, a C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkyl A silyl group, and an arylsilyl group of C ₆ to C ₄₀ may be substituted with at least one substituent selected from the group consisting of

For example, the C ₆ -C ₄₀ aryl group or the heteroaryl group having 5 to 40 nuclear atoms may be substituted with at least one group selected from phenyl, naphthyl, indene, anthracene, phenanthrene, pyrene, triphenylene, pyridine, pyrimidine, pyrazine, And examples thereof include azine, quinoline, isoquinoline, quinoxaline, fluorene, carbazole, dibenzothiophene, dibenzofuran, acridine, indole, benzofuran, benzothiophene, benzimidazole, benzothiazole, It can be Lin.

The compound of formula (1) according to the present invention may be further compounded by any one of the compounds represented by the following formulas (2) to (4).

Where

R ₁ is a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms or NR ₃ R ₄ ;

R ₂ , R ₃ and R ₄ are as defined above.

R ₂ is preferably a C ₆ to C ₄₀ aryl group or a heteroaryl group having 5 to 40 nuclear atoms.

As used herein, “unsubstituted alkyl” is a straight or branched chain saturated hydrocarbon of 1 to 40 (10) carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, Hexyl and the like.

"Unsubstituted aryl" means an aromatic moiety having 6 to 40 (8) carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached to each other in a pendant or condensed form.

"Unsubstituted heteroaryl" means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 40 (8) nucleoatoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, Substituted by heteroatoms such as O and S. Two or more rings may be attached in a pendant or condensed form to each other and further include a condensed form with an aliphatic ring or an aromatic ring.

"Condensation ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compound represented by the formula (1) of the present invention described above may be further embodied by the formulas illustrated below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

For example, the compound represented by the general formula (2) may be further exemplified by the following exemplified compounds 1-1 to 1-20, and the compound represented by the general formula (3) may be exemplified by the following exemplified compounds 2-1 to 2-20 Can be embodied. Further, the compound represented by the above formula (4) can be further compounded by the following exemplified compounds 3-1 to 3-20.

The compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

&Lt; Organic electroluminescent device &

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

More specifically, the organic electroluminescent device according to the present invention includes an anode; A cathode; And at least one organic material layer sandwiched between the anode and the cathode, wherein at least one of the organic material layers includes a compound represented by the formula (1). In this case, the compound represented by Formula 1 may include one kind or two or more kinds.

Here, the organic material layer containing the compound represented by the formula (1) of the present invention may be any one or more of a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer and an electron injecting layer, Lt; / RTI &gt;

The light emitting layer of the organic electroluminescent device according to the present invention may contain a host material, wherein any one of the compounds represented by Formula 1 may be used as the host material. As such, when the light emitting layer contains any one of the compounds represented by Chemical Formula 1, organic electroluminescence having excellent efficiency (light emitting efficiency and power efficiency), lifetime, luminance, driving voltage, etc., because the bonding force between holes and electrons in the light emitting layer is increased. An element can be provided. The compound represented by Formula 1 may be included in an organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material. It can also be used as a dopant material.

The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which one or more organic layers are laminated between electrodes. Non-limiting examples thereof include (i) an anode, a light emitting layer, a cathode; (Ii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode; Or (iii) structures such as an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode.

In addition, as described above, the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between an electrode and an organic material layer.

In the organic EL device according to the present invention, the organic material layer containing the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The organic EL device according to the present invention forms an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Formula 1 of the present invention. It can be manufactured by.

For example, a silicon wafer, quartz or glass plate, a metal plate, a plastic film or a sheet can be used as the substrate.

Examples of the positive electrode material 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 polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[ Synthetic example  1] Compound 9, 9 '- ( quinazoline -1,3 (2H, 4H) -diylbis (4,1-phenylene)) bis (9H-carbazole)

<Step 1> Synthesis of 1,2,3,4-tetrahydroquinazoline

Quinazoline (10 g, 76.8 mmol) was dissolved in 100 mL of tetrahydrofuran, followed by addition of NaBH ₄ (10 g, 264 mmol) and stirring. After stirring for 2 days, it was confirmed by TLC that the reaction was terminated, and distilled water was added thereto and extracted with ethyl acetate. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound (3 g, yield 29%). HRMS [M] &lt; ⁺ & gt ^; : 134.08

Synthesis of 9,9 '- (quinazoline-1,3 (2H, 4H) -diylbis (4,1-phenylene)) bis

The <step 1> 1,2,3,4-tetrahydroquinazoline (3g, 22.3mmol) of 9- (4-bromophenyl) -9H- carbazole (15.8g, 49mmol) obtained _{from, Pd (OAc) 2 (0.25g} , 1.11 mmol) and Cs ₂ CO ₃ (21.7 g, 66.9 mmol) were stirred in toluene (100 ml) at room temperature for 15 minutes. Thereafter, tri- (tert-butyl) phosphine (0.22 g, 1.11 mmol) was slowly added dropwise and the reaction mixture was refluxed for 24 hours.

After the reaction was completed, distilled water was added and the mixture was extracted with dichloromethyl solution. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound 1-1 (8 g, yield 58%). HRMS [M] &lt; ⁺ & gt ^; : 616.26

Synthesis Example 2 Synthesis of 2,2 '- (quinazoline-1,3 (2H, 4H) -diyl) bis (9,9,10-triphenyl-9,10-dihydroacridine)

The procedure of Synthesis Example 1 was repeated except that 2-bromo-9,9,10-triphenyl-9,10-dihydroacridine was used in place of 9- (4-bromophenyl) -9H- -2 (yield: 85%). HRMS [M] &lt; ⁺ & gt ^; : 949.19

Synthesis Example 3 Synthesis of 3,3 '- (quinazoline-1,3 (2H, 4H) -diyl) bis (9-phenyl-9H-carbazole)

(Yield 76%) was obtained by following the same procedure as in Synthesis Example 1, except that 3-bromo-9-phenyl-9H-carbazole was used in place of 9- (4-bromophenyl) ). HRMS [M] &lt; ⁺ & gt ^; : 616.75

Synthesis Example 4 Synthesis of Compound 3- (9,9'-spirobi [fluoren] -2-yl) -1- (9,9'-spirobi [fluoren] -7- Synthesis of tetrahydroquinazoline

The same procedure as in Synthesis Example 1 was repeated but using 2-bromo-9,9'-spirobi [fluorene] instead of 9- (4-bromophenyl) -9H- 57%). HRMS [M] &lt; ⁺ & gt ^; : 762.94

Synthesis Example 5 Synthesis of Compound 1,3-bis (4,6-diphenylpyridin-2-yl) -1,2,3,4-tetrahydroquinazoline

(Yield 76%) was obtained by following the same procedure as in Synthesis Example 1, except that 2-bromo-4,6-diphenylpyridine was used in place of 9- (4-bromophenyl) -9H- . HRMS [M] &lt; ⁺ & gt ^; : 592.73

Synthesis Example 6 Synthesis of Compound N-phenyl-N- (4- (1- (9-phenyl-9H-carbazol-3-yl) -1,2- dihydroquinazolin- Synthesis of -amine

Dibenzo [b, d] thiophene instead of 4- (4-bromophenyl) -9H-carbazole was used in place of 4- (4-bromophenyl) Yield: 68%). HRMS [M] &lt; ⁺ & gt ^; : 650.85

Synthesis Example 7 Synthesis of Compound 1,3-bis (4- (dibenzo [b, d] thiophen-4-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedure as in Synthesis Example 1 was carried out except that N- (4-bromophenyl) -N-phenylnaphthalen-1-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 79%). HRMS [M] &lt; ⁺ & gt ^; : 720.90

Synthesis Example 8 Synthesis of Compound N-phenyl-N- (4- (1- (9-phenyl-9H-carbazol-3-yl) -1,2- dihydroquinazolin- Synthesis of -amine

The same procedures as in Synthesis Example 1 were carried out except that N- (4-bromophenyl) -N-phenylnaphthalen-2-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 76%). HRMS [M] &lt; ⁺ & gt ^; : 720.90

Synthesis Example 9 Synthesis of 9,9 '- (5,5' - (quinazoline-1,3 (2H, 4H) -diyl) bis (pyridine-5,2-diyl)) bis (9H-

The same procedure as in Synthesis Example 1 was carried out except that 9- (5-bromopyridin-2-yl) -9H-carbazole was used in place of 9- (4-bromophenyl) -9H- (Yield: 80%). HRMS [M] &lt; ⁺ & gt ^; : 618.73

Synthesis Example 10 Synthesis of Compound 1,3-bis (9,9-dimethyl-9H-fluoren-3-yl) -1,2,3,4-tetrahydroquinazoline

The procedure of Synthesis Example 1 was repeated except for using 3-bromo-9,9-dimethyl-9H-fluorene instead of 9- (4-bromophenyl) -9H- 70%). HRMS [M] &lt; ⁺ & gt ^; : 518.69

Synthesis Example 11 Synthesis of 9,9 '- (quinazoline-1,3 (2H, 4H) -diylbis (3,1-phenylene)) bis (9H-carbazole)

(Yield: 72%) was obtained by following the same procedure as in Synthesis Example 1, except that 9- (3-bromophenyl) -9H-carbazole was used in place of 9- (4-bromophenyl) ). HRMS [M] &lt; ⁺ & gt ^; : 616.75

Synthesis Example 12 Synthesis of 9,9 '- (5,5' - (quinazoline-1,3 (2H, 4H) -diyl) bis (pyridine-5,3-diyl)) bis (9H-

The same procedures as in Synthesis Example 1 were carried out except that 9- (5-bromopyridin-3-yl) -9H-carbazole was used in place of 9- (4-bromophenyl) -9H- (Yield: 65%). HRMS [M] &lt; ⁺ & gt ^; : 618.73

Synthesis Example 13 Synthesis of Compound 1,3-bis (3- (imidazo [1,2-a] pyridin-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedure as in Synthesis Example 1 was carried out except that 2- (3-bromophenyl) imidazo [1,2-a] pyridine was used in place of 9- (4-bromophenyl) -9H- 15 (yield: 75%). HRMS [M] &lt; ⁺ & gt ^; : 518.61

Synthesis Example 14 Synthesis of Compound 1,3-bis (3- (1-phenyl- 1H-benzo [d] imidazol-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedure as in Synthesis Example 1 was carried out except that 2- (3-bromophenyl) -1-phenyl-1H-benzo [d] imidazole was used in place of 9- (4-bromophenyl) Compound 1-16 (yield 88%) was obtained. HRMS [M] &lt; ⁺ & gt ^; : 670.80

Synthesis Example 15 Synthesis of Compound 1,3-bis (4- (4,6-diphenylpyridin-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The procedure of Synthesis Example 1 was repeated except for using 2- (4-bromophenyl) -4,6-diphenylpyridine instead of 9- (4-bromophenyl) -9H-carbazole to obtain the title compound 1-18 74%). HRMS [M] &lt; ⁺ & gt ^; : 744.92

Synthesis Example 16 Synthesis of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl- 1,2-dihydroquinazolin-3 (4H) -yl) phenyl) -9H-fluoren-2-

<Step 1> Synthesis of 1,2,3,4-tetrahydroquinazoline

Quinazoline (10 g, 76.8 mmol) was dissolved in 100 mL of tetrahydrofuran, followed by addition of NaBH ₄ (10 g, 264 mmol) and stirring. After stirring for 2 days, it was confirmed by TLC that the reaction was terminated, and distilled water was added thereto and extracted with ethyl acetate. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound (3 g, yield 29%). HRMS [M] &lt; ⁺ & gt ^; : 134.08

<Step 2> Synthesis of 3- (3,4-dihydroquinazolin-1 (2H) -yl) -9-phenyl-9H-carbazole

The <step 1> 1,2,3,4-tetrahydroquinazoline (3g, 22.3mmol) of 3-bromo-9-phenyl- 9H-carbazole (10.7g, 33.45mmol) obtained from, Pd (OAc) ₂ (0.25g , 1.11 mol) and Cs ₂ CO ₃ (14.53 g, 44.6 mmol) in 100 ml of toluene, and the mixture was stirred at room temperature for 15 minutes. Thereafter, tri- (tert-butyl) phosphine (0.22 g, 1.11 mmol) was slowly added dropwise and the reaction mixture was refluxed for 24 hours.

After the reaction was completed, distilled water was added and the mixture was extracted with dichloromethyl solution. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound (3.2 g, yield 38%). HRMS [M] &lt; ⁺ & gt ^; : 375.17

Step 3: Synthesis of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl- , 2-dihydroquinazolin-3 (4H) -yl) phenyl) -9H-fluoren-2-

9- phenyl-9H-carbazole (3.2 g, 8.52 mmol) obtained in the above Step 2 was dissolved in N - ([1,1'-biphenyl] (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine (4.4 g, 8.52 mmol), Pd (OAc) ₂ (0.09 g, 0.426 mmol), Cs ₂ CO ₃ (5.55 g, 17.04 mmol) in 100 ml of toluene was stirred at room temperature for 15 minutes. Thereafter, tri- (tert-butyl) phosphine (0.08 g, 0.426 mmol) was slowly added dropwise and the reaction mixture was refluxed for 24 hours.

After the reaction was completed, distilled water was added and the mixture was extracted with dichloromethyl solution. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound 1-17 (4 g, yield 56%). HRMS [M] &lt; ⁺ & gt ^; : 810.37

Synthesis Example 17 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 16 were carried out except that N- (4-bromophenyl) -N-phenylnaphthalen-2-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 66%). HRMS [M] &lt; ⁺ & gt ^; : 668.83

Synthesis Example 18 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

Following the same procedure as in Synthesis Example 16, except for using N- (4-bromophenyl) -N-phenylnaphthalen-1-amine instead of 9- (4-bromophenyl) -9H- (Yield: 56%). HRMS [M] &lt; ⁺ & gt ^; : 668.83

Synthesis Example 19 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 16 were carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used in place of 9- (4-bromophenyl) -9H- -19 (yield: 63%). HRMS [M] &lt; ⁺ & gt ^; : 606.72

Synthesis Example 20 Synthesis of Compound 3- 3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -3,4-dihydroquinazolin-1 (2H) Synthesis of 9-phenyl-9H-carbazole

The same procedure as in Synthesis Example 16 was carried out except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used in place of 9- (4-bromophenyl) -9H- To obtain the title compound 1-20 (yield: 56%). HRMS [M] &lt; ⁺ & gt ^; : 682.81

Synthesis Example 21 Synthesis of 9,9 '- (pyrimido [4,5-d] pyrimidine-1,3 (2H, 4H) -diylbis (4,1-phenylene)

The title compound 2-1 (yield 30%) was synthesized by following the procedure of Synthesis Example 1, except that pyrimido [4,5-d] pyrimidine was used instead of quinoxaline. HRMS [M] &lt; ⁺ & gt ^; : 618.25

Synthesis Example 22 Synthesis of 2,2 '- (quinazoline-1,3 (2H, 4H) -diyl) bis (9,9,10-triphenyl-9,10-dihydroacridine)

The same procedures as in Synthesis Example 21 were carried out except that 2-bromo-9,9,10-triphenyl-9,10-dihydroacridine was used in place of 9- (4-bromophenyl) -9H- -2 (70% yield). HRMS [M] &lt; ⁺ & gt ^; : 951.16

Synthesis Example 23 Synthesis of 3,3 '- (quinazoline-1,3 (2H, 4H) -diyl) bis (9-phenyl-9H-carbazole)

(Yield: 80%) was obtained by following the same procedure as in Synthesis Example 21, except that 3-bromo-9-phenyl-9H-carbazole was used in place of 9- (4-bromophenyl) ). HRMS [M] &lt; ⁺ & gt ^; : 618.73

Synthesis Example 24 Synthesis of Compound 3- (9,9'-spirobi [fluoren] -2-yl) -1- (9,9'-spirobi [fluoren] -7- Synthesis of tetrahydroquinazoline

The same procedure as in Synthesis Example 21 was repeated but using 2-bromo-9,9'-spirobi [fluorene] instead of 9- (4-bromophenyl) -9H- 68%). HRMS [M] &lt; ⁺ & gt ^; : 764.91

Synthesis Example 25 Synthesis of Compound 1,3-bis (4,6-diphenylpyridin-2-yl) -1,2,3,4-tetrahydroquinazoline

(Yield 78%) was obtained by following the same procedure as in Synthesis Example 21, except that 2-bromo-4,6-diphenylpyridine was used in place of 9- (4-bromophenyl) -9H- . HRMS [M] &lt; ⁺ & gt ^; : 594.71

Synthesis Example 26 Synthesis of Compound N-phenyl-N- (4- (1- (9-phenyl-9H-carbazol-3-yl) -1,2-dihydroquinazolin- Synthesis of -amine

Following the same procedure as in Synthesis Example 21, except for using 4- (4-bromophenyl) dibenzo [b, d] thiophene instead of 9- (4-bromophenyl) -9H- Yield: 80%). HRMS [M] &lt; ⁺ & gt ^; : 652.83

Synthesis Example 27 Synthesis of Compound 1,3-bis (4- (dibenzo [b, d] thiophen-4-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedures as in Synthesis Example 21 were carried out except that N- (4-bromophenyl) -N-phenylnaphthalen-1-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 79%). HRMS [M] &lt; ⁺ & gt ^; : 722.88

Synthesis Example 28 Synthesis of Compound N-phenyl-N- (4- (1- (9-phenyl-9H-carbazol-3-yl) -1,2- dihydroquinazolin- Synthesis of -amine

The same procedures as in Synthesis Example 21 were carried out except that N- (4-bromophenyl) -N-phenylnaphthalen-2-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 36%). HRMS [M] &lt; ⁺ & gt ^; : 722.88

Synthesis Example 29 Synthesis of 9,9 '- (5,5' - (quinazoline-1,3 (2H, 4H) -diyl) bis (pyridine-5,2-diyl)) bis (9H-

The same procedures as in Synthesis Example 21 were carried out except that 9- (5-bromopyridin-2-yl) -9H-carbazole was used in place of 9- (4-bromophenyl) -9H- (Yield: 50%). HRMS [M] &lt; ⁺ & gt ^; : 620.70

Synthesis Example 30 Synthesis of Compound 1,3-bis (9,9-dimethyl-9H-fluoren-3-yl) -1,2,3,4-tetrahydroquinazoline

The same procedures as in Synthesis Example 21 were carried out except that 3-bromo-9,9-dimethyl-9H-fluorene was used in place of 9- (4-bromophenyl) -9H- 65%). HRMS [M] &lt; ⁺ & gt ^; : 520.67

Synthesis Example 31 Synthesis of 9,9 '- (quinazoline-1,3 (2H, 4H) -diylbis (3,1-phenylene)) bis (9H-carbazole)

The title compound 2-13 (yield 60%) was obtained by following the same procedure as in Synthesis Example 21, except using 9- (3-bromophenyl) -9H-carbazole instead of 9- (4-bromophenyl) ). HRMS [M] &lt; ⁺ & gt ^; : 618.73

Synthesis Example 32 Synthesis of 9,9 '- (5,5' - (quinazoline-1,3 (2H, 4H) -diyl) bis (pyridine-5,3-diyl)) bis (9H-

The same procedures as in Synthesis Example 21 were carried out except that 9- (5-bromopyridin-3-yl) -9H-carbazole was used in place of 9- (4-bromophenyl) -9H- (Yield: 70%). HRMS [M] &lt; ⁺ & gt ^; : 620.70

Synthesis Example 33 Synthesis of Compound 1,3-bis (3- (imidazo [1,2-a] pyridin-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The procedure of Synthetic Example 21 was repeated except for using 2- (3-bromophenyl) imidazo [1,2-a] pyridine instead of 9- (4-bromophenyl) -9H- 15 (yield: 71%). HRMS [M] &lt; ⁺ & gt ^; : 520.59

Synthesis Example 34 Synthesis of Compound 1,3-bis (3- (1-phenyl- 1H-benzo [d] imidazol-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The procedure of Synthesis Example 21 was repeated except that 2- (3-bromophenyl) -1-phenyl-1H-benzo [d] imidazole was used in place of 9- (4-bromophenyl) Compound 2-16 (yield: 78%) was obtained. HRMS [M] &lt; ⁺ & gt ^; : 672.78

Synthesis Example 35 Synthesis of Compound 1,3-bis (4- (4,6-diphenylpyridin-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

Following the same procedure as in Synthesis Example 21, except for using 2- (4-bromophenyl) -4,6-diphenylpyridine instead of 9- (4-bromophenyl) -9H- 55%). HRMS [M] &lt; ⁺ & gt ^; : 746.90

[ Synthetic example  36] Compound N - ([1,1'- biphenyl ]-4- yl ) -9,9- dimethyl Yl) -1,2-dihydropyrimido [4,5-d] pyrimidin-3 (4H) -yl) phenyl) -9H-fluorene -2-amine

The title compound 2-17 (yield 12%) was synthesized by following the procedure of Synthesis Example 16, except that pyrimido [4,5-d] pyrimidine was used instead of quinoxaline. HRMS [M] &lt; ⁺ & gt ^; : 812.36

Synthesis Example 37 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 36 were carried out, except that N- (4-bromophenyl) -N-phenylnaphthalen-2-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 50%). HRMS [M] &lt; ⁺ & gt ^; : 670.80

Synthesis Example 38 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 36 were carried out, except that N- (4-bromophenyl) -N-phenylnaphthalen-1-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 68%). HRMS [M] &lt; ⁺ & gt ^; : 670.80

Synthesis Example 39 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 36 were carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used in place of 9- (4-bromophenyl) -9H- -19 (yield: 74%). HRMS [M] &lt; ⁺ & gt ^; : 608.69

Synthesis Example 40 Synthesis of Compound 3- (4- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -3,4- dihydroquinazolin- Synthesis of 9-phenyl-9H-carbazole

The same procedure as in Synthesis Example 36 was carried out except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used in place of 9- (4-bromophenyl) -9H- To obtain the title compound 2-20 (yield: 70%). HRMS [M] &lt; ⁺ & gt ^; : 684.79

Synthesis Example 41 Synthesis of 9,9 '- ((4-phenylquinazoline-1,3 (2H, 4H) -diyl) bis (4,1-phenylene)) bis

<Step 1> 4- phenyl -1,2,3,4- tetrahydroquinazoline  synthesis

(Z) - (2-aminophenyl) (phenyl) methanone oxime (10 g, 47.1 mmol) was dissolved in ethanol (100 mL), followed by addition of 10 g of paraformaldehyde . 3 ml of ammonium hydroxide is slowly added dropwise over 15 minutes, then the temperature is gradually increased. After refluxing for 4 hours, the reaction was terminated by TLC. Distilled water was added and extracted with ethyl acetate. The organic layer is dried over Na ₂ SO ₄ and purified by distillation under a reduced pressure and then purified by column chromatography to give the title compound (8.1g, 82% yield). HRMS [M] &lt; ⁺ & gt ^; : 210.12

Step 2 Synthesis of 9-phenyl-3- (4-phenyl-3,4-dihydroquinazolin-1 (2H) -yl) -9H-carbazole

The <step 1> 4-phenyl-1,2,3,4- tetrahydroquinazoline (8g, 38mmol) of 9- (4-bromophenyl) -9H- carbazole (25.7g, 79.8mmol) obtained from, Pd (OAc) ₂ (0.42 g, 1.9 mmol) and Cs ₂ CO ₃ (37 g, 114 mmol) in 150 ml of toluene at room temperature for 15 minutes. Thereafter, tri- (tert-butyl) phosphine (0.38 g, 1.9 mmol) was slowly added dropwise and the reaction mixture was refluxed for 24 hours.

After the reaction was completed, distilled water was added and the mixture was extracted with dichloromethyl solution. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to give the title compound 3-1 (18.42 g, yield 70%). HRMS [M] &lt; ⁺ & gt ^; : 692.29

Synthesis Example 42 Synthesis of 2,2 '- (quinazoline-1,3 (2H, 4H) -diyl) bis (9,9,10-triphenyl-9,10-dihydroacridine)

The same procedures as in Synthesis Example 41 were carried out except that 2-bromo-9,9,10-triphenyl-9,10-dihydroacridine was used in place of 9- (4-bromophenyl) -9H- -2 (yield: 58%). HRMS [M] &lt; ⁺ & gt ^; : 1025.28

Synthesis Example 43 Synthesis of 3,3 '- (quinazoline-1,3 (2H, 4H) -diyl) bis (9-phenyl-9H-carbazole)

The title compound 3-3 (yield 60%) was obtained by following the same procedure as in Synthesis 41, but using 3-bromo-9-phenyl-9H-carbazole instead of 9- (4-bromophenyl) ). HRMS [M] &lt; ⁺ & gt ^; : 692.85

Synthesis Example 44 Synthesis of Compound 3- (9,9'-spirobi [fluoren] -2-yl) -1- (9,9'-spirobi [fluoren] -7- Synthesis of tetrahydroquinazoline

The same procedure as in Synthesis Example 41 was repeated but using 2-bromo-9,9'-spirobi [fluorene] instead of 9- (4-bromophenyl) -9H- 62%). HRMS [M] &lt; ⁺ & gt ^; : 839.03

[Synthesis Example 45] Synthesis of 1,3-bis (4,6-diphenylpyridin-2-yl) -1,2,3,4-tetrahydroquinazoline

(Yield 68%) was obtained by following the same procedure as in Synthesis Example 41, except that 2-bromo-4,6-diphenylpyridine was used in place of 9- (4-bromophenyl) -9H- . HRMS [M] &lt; ⁺ & gt ^; : 668.83

Synthesis Example 46 Synthesis of Compound N-phenyl-N- (4- (1- (9-phenyl-9H-carbazol-3-yl) -1,2-dihydroquinazolin- Synthesis of -amine

Dibenzo [b, d] thiophene instead of 4- (4-bromophenyl) -9H-carbazole was used in place of 4- (4-bromophenyl) Yield: 70%). HRMS [M] &lt; ⁺ & gt ^; : 726.95

Synthesis Example 47 Synthesis of Compound 1,3-bis (4- (dibenzo [b, d] thiophen-4-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedures as in Synthesis Example 41 were carried out, except that N- (4-bromophenyl) -N-phenylnaphthalen-1-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 71%). HRMS [M] &lt; ⁺ &gt;: 797.00

Synthesis Example 48 Synthesis of Compound N-phenyl-N- (4- (1- (9-phenyl-9H-carbazol-3-yl) -1,2- dihydroquinazolin- Synthesis of -amine

The same procedures as in Synthesis Example 41 were carried out, except that N- (4-bromophenyl) -N-phenylnaphthalen-2-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 66%). HRMS [M] &lt; ⁺ &gt;: 797.00

Synthesis Example 49 Synthesis of 9,9 '- (5,5'- (quinazoline-1,3 (2H, 4H) -diyl) bis (pyridine-5,2-diyl)) bis (9H-

The same procedures as in Synthesis Example 41 were carried out except that 9- (5-bromopyridin-2-yl) -9H-carbazole was used in place of 9- (4-bromophenyl) -9H- (Yield: 60%). HRMS [M] &lt; ⁺ & gt ^; : 694.82

Synthesis Example 50 Synthesis of 1,3-bis (9,9-dimethyl-9H-fluoren-3-yl) -1,2,3,4-tetrahydroquinazoline

The same procedure as in Synthesis Example 41 was repeated but using 3-bromo-9,9-dimethyl-9H-fluorene instead of 9- (4-bromophenyl) -9H- 52%). HRMS [M] &lt; ⁺ & gt ^; : 594.79

Synthesis Example 51 Synthesis of 9,9 '- (quinazoline-1,3 (2H, 4H) -diylbis (3,1-phenylene)) bis (9H-carbazole)

The title compound 3-13 (yield 54%) was prepared using the same procedure as in Synthesis 41, except that 9- (3-bromophenyl) -9H-carbazole was used in place of 9- (4-bromophenyl) ). HRMS [M] &lt; ⁺ & gt ^; : 692.85

Synthesis Example 52 Synthesis of 9,9 '- (5,5' - (quinazoline-1,3 (2H, 4H) -diyl) bis (pyridine-5,3-diyl)) bis (9H-

The same procedures as in Synthesis Example 41 were carried out except that 9- (5-bromopyridin-3-yl) -9H-carbazole was used in place of 9- (4-bromophenyl) -9H- (Yield: 64%). HRMS [M] &lt; ⁺ & gt ^; : 694.82

Synthesis Example 53 Synthesis of 1,3-bis (3- (imidazo [1,2-a] pyridin-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedure as in Synthesis Example 41 was performed, except that 2- (3-bromophenyl) imidazo [1,2-a] pyridine was used in place of 9- (4-bromophenyl) -9H- 15 (yield: 70%). HRMS [M] &lt; ⁺ & gt ^; : 594.71

Synthesis Example 54 Synthesis of 1,3-bis (3- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedure as in Synthesis Example 41 was carried out except that 2- (3-bromophenyl) -1-phenyl-1H-benzo [d] imidazole was used in place of 9- (4-bromophenyl) Compound 3-16 (yield: 65%) was obtained. HRMS [M] &lt; ⁺ & gt ^; : 746.90

Synthesis Example 55 Synthesis of 1,3-bis (4- (4,6-diphenylpyridin-2-yl) phenyl) -1,2,3,4-tetrahydroquinazoline

The same procedure as in Synthesis Example 41 was repeated but using 2- (4-bromophenyl) -4,6-diphenylpyridine instead of 9- (4-bromophenyl) -9H- 60%). HRMS [M] &lt; ⁺ & gt ^; : 821.02

Synthesis Example 56 Synthesis of Compound N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (8- (9- -7,8-dihydropteridin-5 (6H) -yl) phenyl) -9H-fluoren-2-amine

<Step 1> Synthesis of 4-phenyl-1,2,3,4-tetrahydroquinazoline

(Z) - (2-aminophenyl) (phenyl) methanone oxime (10 g, 47.1 mmol) was dissolved in ethanol (100 mL), followed by addition of 10 g of paraformaldehyde . 3 ml of ammonium hydroxide is slowly added dropwise over 15 minutes, then the temperature is gradually increased. After refluxing for 4 hours, the reaction was terminated by TLC. Distilled water was added and extracted with ethyl acetate. The organic layer is dried over Na ₂ SO ₄ and purified by distillation under a reduced pressure and then purified by column chromatography to give the title compound (8.1g, 82% yield).

HRMS [M] &lt; ⁺ & gt ^; : 210.12

Synthesis of 9-phenyl-3- (4-phenyl-3,4-dihydroquinazolin-1 (2H) -yl) -9H-carbazole

9-phenyl-9H-carbazole (14.7 g, 45.6 mmol), Pd (OAc) 4-phenyl-1,2,3,4-tetrahydroquinazoline (8 g, 38.04 mmol) ₂ (0.42 g, 1.9 mol) and Cs ₂ CO ₃ (24.7 g, 76.08 mmol) in 200 ml of toluene at room temperature for 15 minutes. Thereafter, tri- (tert-butyl) phosphine (0.38 g, 1.9 mmol) was slowly added dropwise and the reaction mixture was refluxed for 24 hours.

After the reaction was completed, distilled water was added and the mixture was extracted with dichloromethyl solution. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound (8.5 g, yield 50%). HRMS [M] &lt; ⁺ & gt ^; : 451.2

Step 3: Synthesis of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl- yl) -1,2-dihydroquinazolin-3 (4H) -yl) phenyl) -9H-fluoren-

9-phenyl-3- (4-phenyl-3,4-dihydroquinazolin-1 (2H) -yl) -9H-carbazole (8.5 g, 18.8 mmol) obtained in the above Step 2 was dissolved in N - (11.66 g, 22.5 mmol), Pd (OAc) ₂ (0.21 g, 0.94 mmol) was added to a solution of 4- ) And Cs ₂ CO ₃ (12.2 g, 37.6 mmol) in 150 ml of toluene, and the mixture was stirred at room temperature for 15 minutes. Thereafter, tri- (tert-butyl) phosphine (0.19 g, 0.94 mmol) was slowly added dropwise and the reaction mixture was refluxed for 24 hours.

After the reaction was completed, distilled water was added and the mixture was extracted with dichloromethyl solution. The organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound 3-17 (7.4 g, yield 44.5%). HRMS [M] &lt; ⁺ & gt ^; : 886.4

Synthesis Example 57 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 56 were carried out, except that N- (4-bromophenyl) -N-phenylnaphthalen-2-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 51%). HRMS [M] &lt; ⁺ & gt ^; : 744.92

Synthesis Example 58 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 56 were carried out, except that N- (4-bromophenyl) -N-phenylnaphthalen-1-amine was used in place of 9- (4-bromophenyl) -9H- (Yield: 48%). HRMS [M] &lt; ⁺ & gt ^; : 744.92

Synthesis Example 59 Synthesis of Compound 3- (4,6-diphenyl-1,3,5-triazin-2-yl) -3,4-dihydroquinazolin-1 (2H) Synthesis of -carbazole

The same procedures as in Synthesis Example 56 were carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used in place of 9- (4-bromophenyl) -9H- -19 (yield: 56%). HRMS [M] &lt; ⁺ & gt ^; : 682.81

Synthesis Example 60 Synthesis of Compound 3- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -3,4-dihydroquinazolin-1 (2H) Synthesis of 9-phenyl-9H-carbazole

The same procedure as in Synthesis Example 56 was carried out except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used in place of 9- (4-bromophenyl) -9H- To obtain the title compound 3-20 (yield 66%). HRMS [M] &lt; ⁺ & gt ^; : 758.91

[Examples 1 to 21] Production of green organic EL device

The compounds (1-1, 1-3, 1-4, 1-6, 1-9, 1-12, 1-13, 2-1, 2-3, 2-4, 3-, 3-, 3-, 3-, 3-, 3-, 3-, 3-, 3-, After performing the sublimation purification, a green organic EL device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

M-MTDATA (60 nm) / TCTA (80 nm) / Compounds 1-1, 1-3, 1-4, 1-6, 1-9, 1-12, 1-13, -1, 2-3, 2-4, 2-6, 2-9, 2-12, 2-13, 3-1, 3-3, 3-4, 3-6, 3-9, 3-12 , 3-13 (each) + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al Respectively.

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

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound 1-1 as a luminescent host material in forming the light emitting layer.

[Evaluation Example 1]

The driving voltage, current efficiency and emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 1 to 21 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 1-1 6.1 512 41.1 Example 2 1-3 5.9 516 42.3 Example 3 1-4 5.8 515 39.1 Example 4 1-6 6.3 514 40.1 Example 5 1-9 5.9 513 41.6 Example 6 1-12 5.8 515 39.6 Example 7 1-13 6.3 514 40.8 Example 8 2-1 5.8 512 40.6 Example 9 2-3 6.3 516 39.9 Example 10 2-4 6.1 515 39.8 Example 11 2-6 5.9 514 41.3 Example 12 2-9 6.1 515 40.5 Example 13 2-12 5.9 514 45.2 Example 14 2-13 5.8 514 42.3 Example 15 3-1 6.4 514 39.4 Example 16 3-3 5.9 512 41.0 Example 17 3-4 5.7 516 40.8 Example 18 3-6 6.1 515 39.5 Example 19 3-9 6.5 514 40.3 Example 20 3-12 5.9 513 41.1 Example 21 3-13 5.8 514 40.5 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL devices of Examples 1 to 21 using the compound according to the present invention as a light emitting layer had higher efficiency and driving voltage than the green organic EL device of Comparative Example 1 using conventional CBP It can be seen that it exhibits better performance in terms of surface area.

[Examples 22 to 48] Preparation of blue organic EL device

The compounds (1-5, 1-11, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 2-5, 2 -11, 2-14, 2-15, 2-16, 2-17, 2-18, 2-19, 2-20, 3-5, 3-11, 3-14, 3-15, 3-16 , 3-17, 3-18, 3-19, 3-20) were subjected to high purity sublimation purification by a conventionally known method, and blue organic EL devices were fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

On this ITO transparent electrode, CuPc (10 nm) / TPAC (30 nm) / Compounds 1-5, 1-11, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19 , 1-20, 2-5, 2-11, 2-14, 2-15, 2-16, 2-17, 2-18, 2-19, 2-20, 3-5, 3-11, 3 (30 nm) / Alq ₃ (30 nm) / LiF (0.2 nm) / 7, respectively) + 14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20 Al (150 nm) were stacked in this order to fabricate an organic EL device.

The structures of CuPc, TPAC, and Flrpic are as follows.

Comparative Example 2 Fabrication of Organic EL Device

A blue organic EL device was fabricated in the same manner as in Example 22, except that CBP was used instead of Compound 1-5 as a luminescent host material in forming the light emitting layer.

[Evaluation Example 2]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the blue organic EL devices manufactured in Examples 22 to 48 and Comparative Example 2, and the results are shown in Table 2 below.

Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 22 1-5 7.24 474 5.96 Example 23 1-11 7.7 478 5.89 Example 24 1-14 7.42 476 6.11 Example 25 1-15 7.67 477 5.85 Example 26 1-16 7.49 475 5.81 Example 27 1-17 7.6 473 5.9 Example 28 1-18 7.39 473 6.17 Example 29 1-19 7.28 472 5.99 Example 30 1-20 7.32 473 6.24 Example 31 2-5 7.4 475 6.05 Example 32 2-11 7.42 474 6.11 Example 33 2-14 7.32 476 5.89 Example 34 2-15 7.49 474 5.85 Example 35 2-16 7.7 477 5.61 Example 36 2-17 7.43 476 5.81 Example 37 2-18 7.20 473 5.88 Example 38 2-19 7.35 475 5.64 Example 39 2-20 7.24 474 5.9 Example 40 3-5 7.5 471 5.98 Example 41 3-11 7.32 474 6.10 Example 42 3-14 7.5 477 6.43 Example 43 3-15 7.45 476 6.5 Example 44 3-16 7.5 474 6.21 Example 45 3-17 7.6 477 6.11 Example 46 3-18 7.6 473 6.2 Example 47 3-19 7.7 478 6.5 Example 48 3-20 7.42 475 6.11 Comparative Example 2 CBP 7.80 474 5.80

As shown in Table 2, the blue organic EL devices of Examples 22 to 48 using the compound according to the present invention as a light emitting layer had a higher efficiency and a higher driving voltage than the blue organic EL device of Comparative Example 2 using CBP It can be seen that it exhibits better performance in terms of surface area.

Claims (8)

A compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
X and Y are the same or different and are each independently N or CH;
R ₁ and R ₂ are the same or different and each independently represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, -NR ₃ R ₄ , a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, and a substituted or unsubstituted 3 to 40 Or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with a group adjacent to the condensed aliphatic ring, condensed aromatic ring, condensed heteroaromatic ring or condensed heteroaromatic ring,
Wherein R ₃ and R ₄ are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted nucleus atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, and a substituted or unsubstituted selected from the group consisting of a heterocycloalkyl group of the number of ring nucleus atoms of 3 to 40, or, or they are adjacent And a group forming a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with
R ₅ is H, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms heteroaryl of 5 to 40, a substituted or unsubstituted C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy of, -NR _a R _b, a substituted or unsubstituted selected from the group consisting of a cycloalkyl group of C ₃ ~ C ₄₀ unsubstituted and substituted or unsubstituted heteroaryl number of 3 to 40 nuclear atoms or a cycloalkyl group, or they A group forming a condensed aliphatic ring, a condensed aromatic ring, a condensed hetero aliphatic ring or a condensed heteroaromatic ring,
Wherein R _a and R _b are the same as or different from each other, and each independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryl An oxy group, a substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, and a substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, or groups adjacent thereto are bonded to each other to form a condensed aliphatic ring Can form a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring,
The C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, C ₆ ~ The C ₄₀ to C ₄₀ aryloxy group, the C ₁ to C ₄₀ alkyloxy group, the C ₃ to C ₄₀ cycloalkyl group, and the heterocyclic cycloalkyl group having 3 to 40 nuclear atoms are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the An aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocyclo An alkyl group, a C ₁ to C ₄₀ alkylsilyl group, and a C ₆ to C ₄₀ arylsilyl group. The compound according to claim 1, wherein the compound represented by the formula (1) is any one selected from compounds represented by the following formulas (2) to (4)
(2)

(3)

[Chemical Formula 4]

In this formula,
R ₁ is a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms or NR ₃ R ₄ ;
R ₂ , R ₃ , and R ₄ are as defined in claim 1. The compound according to claim 1, wherein R ₁ and R ₂ are the same or different and each independently is a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms or NR ₃ R ₄ &Lt; / RTI &gt; 3. The compound according to claim 2, wherein the compound represented by the formula (2) is selected from the group of compounds represented by the following formula:

3. The compound according to claim 2, wherein the compound represented by the formula (3) is selected from the group of compounds represented by the following formula:

3. The compound according to claim 2, wherein the compound represented by the formula (4) is selected from the group of compounds represented by the following formula:

An organic electroluminescent device comprising: (i) a cathode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 6. The organic electroluminescent device according to claim 7, wherein the compound is contained in at least one layer selected from the group consisting of a light emitting layer, an electron transporting layer and a hole transporting layer.