KR20130114785A - Novel organic electroluminescent compounds and organic electroluminescent device containing the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device containing the same Download PDF

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KR20130114785A
KR20130114785A KR1020120037084A KR20120037084A KR20130114785A KR 20130114785 A KR20130114785 A KR 20130114785A KR 1020120037084 A KR1020120037084 A KR 1020120037084A KR 20120037084 A KR20120037084 A KR 20120037084A KR 20130114785 A KR20130114785 A KR 20130114785A
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compound
organic electroluminescent
substituted
unsubstituted
mmol
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문두현
김남균
구종석
윤석근
조영준
권혁주
이경주
김봉옥
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롬엔드하스전자재료코리아유한회사
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Priority to KR1020120037084A priority Critical patent/KR20130114785A/en
Priority to TW102112302A priority patent/TW201402775A/en
Priority to CN201380019376.0A priority patent/CN104245690A/en
Priority to PCT/KR2013/002954 priority patent/WO2013154325A1/en
Publication of KR20130114785A publication Critical patent/KR20130114785A/en

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Abstract

PURPOSE: An organic electroluminescent compound has excellent luminous efficiency without using a hole-blocking layer and improves power efficiency. CONSTITUTION: An organic electroluminescent compound is represented by chemical formula 1-4. In the chemical formulas, each of X1 and X2 is CRO or N; at least one or more of X1 and X2 is N; each of Ar1, Ar2, and Ar3 is hydrogen, a substituted or unsubstituted C6-30 aryl group; or a substituted or unsubstituted 5-60 membered heteroaryl; each of L1, L2, and L3 is a single bond or a substituted or unsubstituted C6-30 arylene; each of A, B, C, and D ring is a substituted or unsubstituted C6-30 aromatic ring or a substituted or unsubstituted 5-60 membered aromatic hetero ring; and E has a structure represented by chemical formula 5.

Description

신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자{NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE CONTAINING THE SAME}Novel organic electroluminescent compound and organic electroluminescent device including the same {NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE CONTAINING THE SAME}

본 발명은 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다. 보다 구체적으로, 본 발명은 적색 발광 재료로서 우수한 성능을 발휘하는 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. More specifically, the present invention relates to a novel organic electroluminescent compound exhibiting excellent performance as a red luminescent material and an organic electroluminescent device comprising the same.

유기 전계 발광 소자는 애노드와 캐소드 사이에 전압을 가하면 애노드와 캐소드 각각에서 정공과 전자가 주입되고, 이들 정공과 전자가 발광층에서 재결합함으로써 여기자(exiton)를 형성하고, 상기 여기자가 바닥 상태로 전이하면서 그 에너지 차이에 해당하는 파장의 빛을 방출하는 원리를 이용하는 자발광 소자이다.In the organic electroluminescent device, when a voltage is applied between the anode and the cathode, holes and electrons are injected into the anode and the cathode, respectively. These holes and electrons recombine in the light emitting layer to form an exciton. Emitting element using the principle of emitting light of a wavelength corresponding to the energy difference.

이러한 발광은 그 메카니즘에 따라 일중항 상태의 여기자를 이용하는 형광과 삼중항 상태의 여기자를 이용하는 인광으로 나뉘는데, 양자역학적 이유에서 인광 발광 물질이 형광 발광 물질에 비해 4배 정도 높은 발광 효율을 달성할 수 있다는 장점이 있다.Such a luminescence is classified into a fluorescence using a singlet state exciton and a phosphorescence using a triplet state exciton according to the mechanism. For a quantum mechanical reason, a phosphorescent material can achieve luminous efficiency four times higher than that of a fluorescent material .

한편, 이러한 유기 전계 발광 소자에서 발광 재료는 색 순도, 발광 효율 및 안정성을 증가시키기 위해 호스트 물질에 발광 염료(도펀트)를 혼합하여 사용하기도 한다.Meanwhile, in the organic electroluminescent device, a light emitting material (dopant) may be mixed with a host material to increase color purity, luminous efficiency and stability.

이와 같이 발광 재료로서 호스트 물질/도펀트 체계를 사용할 때, 호스트 물질은 발광 소자의 효율과 성능에 큰 영향을 미치므로, 그 선택이 중요하다. 그러나, 종래 기술에서 사용되어 왔던 4,4'-N,N'-디카바졸바이페닐(CBP)과 같은 인광용 호스트 물질은 형광용 물질에 비하여 전류 효율은 높으나, 구동 전압이 높아서 전력 효율 면에서 이점이 없었고, 발광 효율 및 작동 수명도 여전히 개선이 요구된다.When the host material / dopant system is used as the light emitting material, the host material greatly affects the efficiency and performance of the light emitting device, so that selection is important. However, phosphorescent host materials, such as 4,4'-N, N'-dicarbazolebiphenyl (CBP), which have been used in the prior art, have higher current efficiency than fluorescent materials, but have high driving voltages, resulting in power efficiency. There was no advantage, and the luminous efficiency and operating life still need improvement.

국제공개공보 제 WO 2011/132683호 및 WO 2011/132684호는 전자 및 정공 수송 특성을 갖는 비스카르바졸 유도체, 전계 발광 소자의 인광 호스트 물질로서의 이의 용도 및 이를 포함하는 유기 전계 발광 소자를 개시하고 있으나, 개시된 화합물들은 전력 효율 및 발광 효율 면에서 여전히 만족스럽지 못하다.International Publication Nos. WO 2011/132683 and WO 2011/132684 disclose biscarbazole derivatives having electron and hole transport properties, their use as phosphorescent host materials as electroluminescent devices, and organic electroluminescent devices comprising the same. The disclosed compounds are still not satisfactory in terms of power efficiency and luminous efficiency.

국제공개공보 제 WO 2011/132683호International Publication No. WO 2011/132683 국제공개공보 제 WO 2011/132684호International Publication No. WO 2011/132684

본 발명은 상기한 당업계의 요구에 부응하여 창안된 것으로, 발광 효율 및 전력 효율이 우수한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자를 제공하는 것을 목적으로 한다. The present invention was made in response to the above-described demands in the art, and an object thereof is to provide an organic electroluminescent compound having excellent luminous efficiency and power efficiency and an organic electroluminescent device comprising the same.

상기의 기술적 과제를 해결하기 위해 연구한 결과, 본 발명자들은 방향족 환 또는 방향족 헤테로환들을 서로 독립적으로 단일결합으로 연결시키거나 단일결합과 함께 N, S, O 및 C 중 하나 이상의 원자를 사용하여 연결시킨 구조로 된 치환기를 하기 화학식 I의 특정 위치(*로 표시)에 도입하는 경우 적색 발광의 성능이 향상됨을 발견하여 본 발명을 완성하였다.In order to solve the above technical problem, the present inventors have linked an aromatic ring or an aromatic heterocyclic ring to each other independently by a single bond or by using one or more atoms of N, S, O and C together with a single bond. The present invention has been found to improve the performance of red light emission when a substituent having a structure of the above-described structure is introduced at a specific position of the formula (I).

[화학식 I](I)

Figure pat00001
Figure pat00001

상기 화학식 I에서, In the formula (I)

X1 및 X2는 각각 독립적으로 CH 또는 N이고; X 1 and X 2 are each independently CH or N;

Ar1 및 Ar2는 각각 독립적으로 수소, 치환 또는 비치환된 C6-C30 아릴 그룹, 또는 치환 또는 비치환된 5-60원 헤테로아릴 그룹이고; Ar 1 And Ar 2 are each independently hydrogen, substituted or unsubstituted C 6 -C 30 Aryl group or substituted or unsubstituted 5-60 membered heteroaryl group;

* 중 어느 하나는 하기 화학식 II의 구조를 가지며, 다른 하나는 수소, 치환 또는 비치환된 C6-C30 아릴 그룹, 또는 치환 또는 비치환된 5-60원 헤테로아릴 그룹이고;   Any one of * has a structure of Formula II, and the other is hydrogen, substituted or unsubstituted C 6 -C 30 Aryl group or substituted or unsubstituted 5-60 membered heteroaryl group;

[화학식 II]≪ RTI ID = 0.0 &

Figure pat00002
Figure pat00002

상기 화학식 II에서,In Chemical Formula II,

L1 , L2 및 L3는 각각 독립적으로 단일결합이거나 치환 또는 비치환된 C6 -C30 아릴렌이고;L 1 , L 2 And L 3 are each independently a single bond or a substituted or unsubstituted C 6 - C 30 arylene, and;

A, B, C 및 D 환은 각각 독립적으로 치환 또는 비치환된 C6-C30 방향족 환 또는 치환 또는 비치환된 5-60원 방향족 헤테로환이고, 이 때 상기 A 및 D 환에 대한 치환체 중 하나 이상은 인접한 치환체와 함께 융합된 환을 형성할 수 있으며; A, B, C and D ring are each independently substituted or unsubstituted C 6 -C 30 An aromatic ring or a substituted or unsubstituted 5-60 membered aromatic heterocycle, wherein at least one of the substituents for the A and D rings may form a fused ring with an adjacent substituent;

E는 하기 화학식 III의 구조를 가지며, 하기 화학식 III에서, F 및 G는 각각 독립적으로 치환 또는 비치환된 C6-C30 방향족 환 또는 치환 또는 비치환된 5-60원 방향족 헤테로환이고, 이 때 상기 환들에 대한 치환체 중 하나 이상은 인접한 치환체와 함께 융합된 환을 형성할 수 있으며, Z는 단일 결합이고, q는 0 또는 1이고;E has a structure of Formula III, wherein in Formula III, F and G are each independently substituted or unsubstituted C 6 -C 30 An aromatic ring or a substituted or unsubstituted 5-60 membered aromatic heterocycle, wherein at least one of the substituents for the rings may form a fused ring with adjacent substituents, Z is a single bond, q is 0 Or 1;

[화학식 III] [Formula III]

Figure pat00003
Figure pat00003

X 및 Y는 각각 독립적으로 NR1, CR2R3, O 또는 S이고; X and Y are each independently NR 1 , CR 2 R 3 , O or S;

X3는, r=0인 경우에는 NR1, CR2R3, O 또는 S 이고, r=1인 경우에는 N 또는 CR4이며; X 3 is NR 1 , CR 2 R 3 , O or S when r = 0, and N or CR 4 when r = 1;

R1, R2, R3 및 R4는 각각 독립적으로, 수소, 치환 또는 비치환된 C1-C30 알킬, 치환 또는 비치환된 C6-C30 아릴, 또는 치환 또는 비치환된 5-60원 헤테로아릴이고;R 1 , R 2 , R 3 And R 4 are each independently hydrogen, substituted or unsubstituted C 1 -C 30 Alkyl, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted 5-60 membered heteroaryl;

m, n, o, p, r 및 s는 각각 독립적으로 0 또는 1이되, 단 n+o+p는 1 이상이고; m, n, o, p, r and s are each independently 0 or 1, provided that n + o + p is 1 or more;

단, 화학식 I의 Ar1이 페닐이고, Ar2가 수소이며, X1 및 X2 N인 경우, 화학식 II가 하기 구조를 갖는 경우는 제외된다. Provided that Ar 1 in Formula I is phenyl, Ar 2 is hydrogen, and X 1 and X 2 are In the case of N, the case where formula (II) has the following structure is excluded.

Figure pat00004
Figure pat00004

본 발명의 화학식 I의 화합물은 종래 기술의 호스트 물질에 비하여 발광 효율이 좋고, 전력 효율 상승을 유도한다. 따라서, 본 발명의 화학식 I의 화합물을 호스트 물질로 사용하면 고효율 및 우수한 소비전력의 유기 전계 발광 소자를 구현할 수 있다. The compound of formula (I) of the present invention has better luminous efficiency than the host material of the prior art, leading to an increase in power efficiency. Therefore, when the compound of formula (I) of the present invention is used as a host material, an organic EL device having high efficiency and excellent power consumption can be realized.

이하, 본 발명에 대하여 구체적으로 설명한다.Hereinafter, the present invention will be described in detail.

본원에서 “C1-C30 알킬”은 탄소수가 1 내지 30개, 바람직하게는 1 내지 20개, 더 바람직하게는 1 내지 10개, 더더욱 바람직하게는 1 내지 6개인 직쇄 또는 분지쇄 알킬을 의미하고, 예를 들어 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸 및 3급-부틸 등이 있다.As used herein, “C 1 -C 30 Alkyl ”means straight or branched chain alkyl having 1 to 30 carbon atoms, preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6 carbon atoms, for example methyl, ethyl , n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.

본원에서 “C6-C30 아릴” 또는 “C6-C30 아릴렌”은 방향족 탄화수소에서 유래된 단일환 또는 융합환계 라디칼을 의미하고, 환 골격 탄소수가 6 내지 18개인 것이 바람직하다. 예를 들면, 페닐, 바이페닐, 터페닐, 나프틸, 플루오레닐, 페난트레닐, 안트라세닐, 인데닐, 트리페닐레닐, 피레닐, 테트라세닐, 플루오란테닐 등이 있다.As used herein, “C 6 -C 30 Aryl ”or“ C 6 -C 30 Arylene ”means a monocyclic or fused ring radical derived from an aromatic hydrocarbon, and preferably has 6 to 18 ring skeleton carbon atoms. For example, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetrasenyl, fluoranthenyl and the like.

본원에서 “5-60원 헤테로아릴” 또는 “5-60원 헤테로아릴렌”은 B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자를 환 골격 원자로 포함하고 나머지 환 골격 원자가 탄소인 아릴 그룹을 의미하고, 환 골격 원자수가 5 내지 30개인 것이 바람직하다.  상기 헤테로아릴은 바람직하게는 1 내지 4개의 헤테로원자를 가지며, 단일환계이거나 하나 이상의 벤젠 환과 축합된 융합환계일 수 있다. 예를 들어, 푸릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 푸라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단일 환계 헤테로아릴, 벤조푸란일, 벤조티오펜일, 이소벤조푸란일, 디벤조푸란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페녹사진일, 페난트리딘일, 벤조디옥솔릴, 디벤조티오펜일, 9,9-디메틸플루오렌일, 벤조티오페노[2,3-c]피리딘일, 벤조푸로[2,3-c]피리딘일 등의 융합 환계 헤테로아릴 등이 있다.As used herein, “5-60 membered heteroaryl” or “5-60 membered heteroarylene” refers to one or more heteroatoms selected from the group consisting of B, N, O, S, P (═O), Si, and P. It means an aryl group which is contained as an atom and whose remaining ring skeleton atom is carbon, and it is preferable that a ring skeleton atom number is 5-30. The heteroaryl preferably has 1 to 4 heteroatoms, and may be a monocyclic system or a fused ring system condensed with one or more benzene rings. For example, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, triazolyl Monocyclic heteroaryl such as tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, benzoimidazolyl , Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindoleyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinoxalin Nyl, carbazolyl, phenoxazinyl, phenantridinyl, benzodioxolyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, benzothiopheno [2,3-c] pyridinyl, benzofuro [2 And fused ring system heteroaryl such as, 3-c] pyridinyl.

본원에서 “C6-C30 방향족 환”은 단일 환 또는 융합 환일 수 있으며, C6-C18 방향족 환이 바람직하다. 구체예로는 벤젠, 나프탈렌, 페난트렌, 안트라센, 피렌, 크라이센, 아세나프틸렌 등을 들 수 있다. “5-60원 방향족 헤테로환”역시 단일 환 또는 융합 환일 수 있으며, 5 내지 30원인 것이 바람직하다. 구체예로는 피라졸, 이미다졸, 피라진, 피리미딘, 인다졸, 피라진, 피리미딘, 이미다졸, 퓨린, 프탈라진, 나프틸리딘, 퀴녹살린, 퀴나졸린, 신놀린, 프테리딘, 페리미딘, 페난트롤린, 피롤로이미다졸, 피롤로트라이아졸, 피라졸로이미다졸, 피라졸로트라이아졸, 피라졸로피리미딘, 피라졸로트라이아진, 이미다조이미다졸, 이미다조피리다진,이미다조피리딘, 이미다조피라진, 트라이아졸로피리딘, 벤조이미다졸, 나프토이미다졸, 벤즈옥사졸, 나프토옥사졸, 벤조티아졸, 나프토티아졸, 벤조트라이아졸, 테트라자인덴, 트라이아진, 카바졸 등이 있다.As used herein, “C 6 -C 30 Aromatic ring ”may be a single ring or a fused ring, and C 6 -C 18 Aromatic rings are preferred. Specific examples include benzene, naphthalene, phenanthrene, anthracene, pyrene, chrysene, acenaphthylene and the like. “5-60 membered aromatic heterocycle” may also be a single ring or a fused ring, preferably 5 to 30 members. Specific examples include pyrazole, imidazole, pyrazine, pyrimidine, indazole, pyrazine, pyrimidine, imidazole, purine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, perri Midine, phenanthroline, pyrroloimidazole, pyrrolotriazole, pyrazoloimidazole, pyrazolotriazole, pyrazolopyrimidine, pyrazolotriazine, imidazoimidazole, imidazopyridazine, imidazopyridine , Imidazopyrazine, triazolopyridine, benzoimidazole, naphthoimidazole, benzoxazole, naphthooxazole, benzothiazole, naphthothiazole, benzotriazole, tetrazadene, triazine, carbazole, etc. have.

상기 C1-C30 알킬, C6-C30 아릴, 5-60원 헤테로아릴, C6-C30 방향족 환, 5-60원 방향족 헤테로환은 서로 독립적으로 할로겐, 시아노, 카르복실, 니트로, 히드록시, C1-C30 알킬, 할로C1-C30알킬, C2-C30 알케닐, C2-C30 알키닐, C1-C30 알콕시, C1-C30 알킬티오, C3-C30 시클로알킬, C3-C30 시클로알케닐, 3-7원 헤테로시클로알킬, C6-C30 아릴, C6-C30 아릴옥시, C6-C30 아릴티오, 5-60원 헤테로아릴, C6-C30 아릴로 치환된 5-60원 헤테로아릴, 5-60원 헤테로아릴로 치환된 C6-C30 아릴, 트리C1-C30알킬실릴, 트리C6-C30아릴실릴, 디C1-C30알킬C6-C30아릴실릴, C1-C30알킬디C6-C30아릴실릴, 아미노, 모노 또는 디C1-C30알킬아미노, 모노 또는 디C6-C30아릴아미노, C1-C30알킬C6-C30아릴아미노, C1-C30 알킬카보닐, C1-C30 알콕시카보닐, C6-C30 아릴카보닐, 디C6-C30아릴보로닐, 디C1-C30알킬보로닐, C1-C30알킬C6-C30아릴보로닐, C6-C30아르C1-C30알킬 및 C1-C30알킬C6-C30아릴로 이루어진 군으로부터 선택되는 1종 이상으로 치환될 수 있고, 바람직하게는 할로겐, 히드록시, C1-C30 알킬, C1-C30 알콕시, 할로C1-C30알킬, C6-C30 아릴, 5-60원 헤테로아릴, 트리C1-C30알킬실릴, 트리C6-C30아릴실릴, 디C1-C30알킬C6-C30아릴실릴, C1-C30알킬디C6-C30아릴실릴, 아미노, 모노 또는 디C1-C30알킬아미노, 모노 또는 디C6-C30아릴아미노 및 C1-C30알킬C6-C30아릴아미노로 이루어진 군으로부터 선택되는 1종 이상으로 치환될 수 있다.C 1 -C 30 Alkyl, C 6 -C 30 Aryl, 5-60 membered heteroaryl, C 6 -C 30 Aromatic rings, 5-60 membered aromatic heterocycles independently of one another are halogen, cyano, carboxyl, nitro, hydroxy, C 1 -C 30 Alkyl, HaloC 1 -C 30 Alkyl, C 2 -C 30 Alkenyl, C 2 -C 30 Alkynyl, C 1 -C 30 Alkoxy, C 1 -C 30 Alkylthio, C 3 -C 30 Cycloalkyl, C 3 -C 30 Cycloalkenyl, 3-7 membered heterocycloalkyl, C 6 -C 30 Aryl, C 6 -C 30 aryloxy, C 6 -C 30 Arylthio, 5-60 membered heteroaryl, C 6 -C 30 5-60 membered heteroaryl substituted with aryl, C 6 -C 30 substituted with 5-60 membered heteroaryl Aryl, triC 1 -C 30 alkylsilyl, triC 6 -C 30 arylsilyl, diC 1 -C 30 alkylC 6 -C 30 arylsilyl, C 1 -C 30 alkyldiC 6 -C 30 arylsilyl, Amino, mono or diC 1 -C 30 alkylamino, mono or diC 6 -C 30 arylamino, C 1 -C 30 alkylC 6 -C 30 arylamino, C 1 -C 30 alkylcarbonyl, C 1- C 30 Alkoxycarbonyl, C 6 -C 30 Arylcarbonyl, diC 6 -C 30 arylboronyl, diC 1 -C 30 alkylboronyl, C 1 -C 30 alkylC 6 -C 30 arylboronyl, C 6 -C 30 arC 1 -C 30 alkyl and C 1 -C 30 alkylC 6 -C 30 It may be substituted with one or more selected from the group consisting of aryl, preferably halogen, hydroxy, C 1 -C 30 Alkyl, C 1 -C 30 Alkoxy, HaloC 1 -C 30 Alkyl, C 6 -C 30 Aryl, 5-60 membered heteroaryl, triC 1 -C 30 alkylsilyl, triC 6 -C 30 arylsilyl, diC 1 -C 30 alkylC 6 -C 30 arylsilyl, C 1 -C 30 alkyldiC 6- C 30 arylsilyl, amino, mono or diC 1 -C 30 alkylamino, mono or diC 6 -C 30 arylamino and C 1 -C 30 alkylC 6 -C 30 arylamino It may be substituted with one or more kinds.

본 발명의 하나의 양태에서, 본 발명은 하기 화학식 1 내지 4 중 어느 하나로 표시되는 유기 전계 발광 화합물을 제공한다. In one embodiment of the present invention, the present invention provides an organic electroluminescent compound represented by any one of the following formula (1).

[화학식 1][Formula 1]

Figure pat00005
Figure pat00005

[화학식 2](2)

Figure pat00006
Figure pat00006

[화학식 3] (3)

Figure pat00007
Figure pat00007

[화학식 4][Formula 4]

Figure pat00008
Figure pat00008

상기 화학식 1 내지 4에서,In the above Chemical Formulas 1 to 4,

X1 및 X2는 각각 독립적으로 CR0 또는 N이며, X1 및 X2 중 하나 이상은 N이고,X 1 and X 2 are each independently CR 0 or N, and X 1 and X 2 At least one of is N,

Ar1, Ar2 및 Ar3은 각각 독립적으로 수소, 치환 또는 비치환된 C6-C30 아릴 그룹, 또는 치환 또는 비치환된 5-60원 헤테로아릴 그룹인데, 바람직하게는 수소, 치환 또는 비치환된 C6-C18 아릴 그룹, 또는 치환 또는 비치환된 5-30원 헤테로아릴 그룹이고, 구체적인 예는 수소, 페닐, 바이페닐, 디벤조푸란일, 디벤조티오펜일, 9,9-디메틸플루오렌일, 벤조티오페노[2,3-c]피리딘일, 벤조푸로[2,3-c]피리딘일이나, 이에 한정되는 것은 아니고,Ar 1 , Ar 2 and Ar 3 are each independently hydrogen, substituted or unsubstituted C 6 -C 30 Aryl group, or substituted or unsubstituted 5-60 membered heteroaryl group, preferably hydrogen, substituted or unsubstituted C 6 -C 18 Aryl group, or a substituted or unsubstituted 5-30 membered heteroaryl group, specific examples of which are hydrogen, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, benzoti Ofeno [2,3-c] pyridinyl, benzofuro [2,3-c] pyridinyl, but are not limited thereto,

L1, L2 및 L3은 각각 독립적으로 단일결합이거나 치환 또는 비치환된 C6 -C30 아릴렌이고, 바람직하게는 단일결합이거나 치환 또는 비치환된 C6-C18 아릴렌이고, 구체적인 예는 단일결합 또는 페닐렌이나, 이에 한정되는 것은 아니고,L 1, L 2 and L 3 is independently a single bond or a substituted or unsubstituted C 6, respectively - and C 30 arylene, preferably a single bond or a substituted or unsubstituted C 6 -C 18 ring Arylene, specific examples are single bonds or phenylene, but are not limited thereto,

A, B, C 및 D 환은 각각 독립적으로 치환 또는 비치환된 C6-C30 방향족 환 또는 치환 또는 비치환된 5-60원 방향족 헤테로환이고, 이 때 상기 A 및 D 환에 대한 치환체 중 하나 이상은 인접한 치환체와 함께 융합된 환을 형성할 수 있으며, 바람직하게는 치환 또는 비치환된 C6-C18 방향족 환 또는 치환 또는 비치환된 5-30원 방향족 헤테로환이고, 구체적인 예는 벤젠, 나프탈렌, 디벤조푸란, 디벤조티오펜, 9,9-디메틸플루오렌이나, 이에 한정되는 것은 아니고,A, B, C and D ring are each independently substituted or unsubstituted C 6 -C 30 An aromatic ring or a substituted or unsubstituted 5-60 membered aromatic heterocycle, wherein at least one of the substituents for the A and D rings may form a fused ring with adjacent substituents, preferably substituted or unsubstituted Substituted C 6 -C 18 Aromatic rings or substituted or unsubstituted 5-30 membered aromatic heterocycles, and specific examples thereof include, but are not limited to, benzene, naphthalene, dibenzofuran, dibenzothiophene, 9,9-dimethylfluorene,

E는 하기 화학식 5의 구조를 가지며, 하기 화학식 5에서, F 및 G 환은 각각 독립적으로 치환 또는 비치환된 C6-C30 방향족 환 또는 치환 또는 비치환된 5-60원 방향족 헤테로환이고, 이 때 상기 환들에 대한 치환체 중 하나 이상은 인접한 치환체와 함께 융합된 환을 형성할 수 있으며, Z는 단일 결합이고, q는 0 또는 1이며,E has a structure of Formula 5, wherein in Formula 5, F and G ring are each independently substituted or unsubstituted C 6 -C 30 An aromatic ring or a substituted or unsubstituted 5-60 membered aromatic heterocycle, wherein at least one of the substituents for the rings may form a fused ring with adjacent substituents, Z is a single bond, q is 0 Or 1,

[화학식 5] [Chemical Formula 5]

Figure pat00009
Figure pat00009

X3, X 및 Y는 각각 독립적으로 NR1, CR2R3, O 또는 S이고,X 3 , X and Y are each independently NR 1 , CR 2 R 3 , O or S,

R0, R1, R2 및 R3는 각각 독립적으로, 수소, 치환 또는 비치환된 C1-C30 알킬, 치환 또는 비치환된 C6-C30 아릴, 또는 치환 또는 비치환된 5-60원 헤테로아릴이고,R 0 , R 1 , R 2 and R 3 are each independently hydrogen, substituted or unsubstituted C 1 -C 30 Alkyl, substituted or unsubstituted C 6 -C 30 Aryl, or substituted or unsubstituted 5-60 membered heteroaryl,

m, n, o 및 p는 각각 독립적으로 0 또는 1이며, n+o+p는 1 이상이고,m, n, o and p are each independently 0 or 1, n + o + p is 1 or more,

단, 상기 화학식 1 내지 4에서 하기 화합물은 제외된다.However, in the above Chemical Formulas 1 to 4, the following compounds are excluded.

Figure pat00010
Figure pat00010

상기 화학식 1 내지 4의 유기 전계 발광 화합물에는, m=1, n=1, o=0, p=0이고, L2는 단일결합인 유기 전계 발광 화합물, m=0, n=1, o=1 및 p=0인 유기 전계 발광 화합물, m=0, n=1, o=0 및 p=1인 유기 전계 발광 화합물, m=0, n=0, o=0 및 p=1인 유기 전계 발광 화합물,  m=1, n=1, o=0, p=1이고, L2는 단일결합인 유기 전계 발광 화합물 등이 포함된다.In the organic electroluminescent compounds of Formulas 1 to 4, m = 1, n = 1, o = 0, p = 0, L 2 is a single bond organic electroluminescent compound, m = 0, n = 1, o = Organic electroluminescent compounds with 1 and p = 0, organic electroluminescent compounds with m = 0, n = 1, o = 0 and p = 1, organic electroluminescent fields with m = 0, n = 0, o = 0 and p = 1 An organic electroluminescent compound, such as a luminescent compound, m = 1, n = 1, o = 0, p = 1, and L <2> is a single bond, etc. are contained.

상기 화학식 1의 유기 전계 발광 화합물의 예로 하기 화학식 6 내지 20을 들 수 있다.Examples of the organic electroluminescent compound of Chemical Formula 1 include the following Chemical Formulas 6 to 20.

Figure pat00011
Figure pat00011

Figure pat00012
Figure pat00012

Figure pat00013
Figure pat00013

Figure pat00014
Figure pat00014

Figure pat00015
Figure pat00015

상기 화학식 6 내지 20에서,In Chemical Formulas 6 to 20,

Ar1 , Ar2 , L1 , L2, X 및 Y는 상기 화학식 1의 정의와 동일하고,Ar 1 , Ar 2 , L 1 , L 2 , X and Y are the same as defined in Formula 1,

R5 내지 R7은 각각 독립적으로, 수소, 치환 또는 비치환된 C6-C30 아릴, 또는 치환 또는 비치환된 5-60원 헤테로아릴이다.
R 5 to R 7 are each independently hydrogen, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted 5-60 membered heteroaryl.

또한, 상기 화학식 2의 유기 전계 발광 화합물의 예로 하기 화학식 21 내지 24를 들 수 있다.In addition, examples of the organic electroluminescent compound of Chemical Formula 2 include the following Chemical Formulas 21 to 24.

Figure pat00016
Figure pat00016

Figure pat00017
Figure pat00017

상기 화학식 21 내지 24에서,In Chemical Formulas 21 to 24,

Ar1 , Ar2 , L1, X 및 Y는 상기 화학식 2에서의 정의와 동일하고,Ar 1 , Ar 2 , L 1 , X and Y are the same as defined in Formula 2,

R5 및 R6는 각각 독립적으로, 수소, 치환 또는 비치환된 C6-C30 아릴, 또는 치환 또는 비치환된 5-60원 헤테로아릴이다.
R 5 and R 6 are each independently hydrogen, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted 5-60 membered heteroaryl.

또한, 상기 화학식 3의 유기 전계 발광 화합물의 예로 하기 화학식 25 내지 27을 들 수 있다.In addition, examples of the organic electroluminescent compound of Chemical Formula 3 include the following Chemical Formulas 25 to 27.

Figure pat00018
Figure pat00018

상기 화학식 25 내지 27에서,In Chemical Formulas 25 to 27,

Ar1 , Ar2 , R1, L3, X 및 Y는 상기 화학식 3에서의 정의와 동일하다.
Ar 1 , Ar 2 , R 1 , L 3 , X and Y are the same as defined in the formula (3).

또한, 상기 화학식 4의 유기 전계 발광 화합물의 예로 하기 화학식 28 내지 31을 들 수 있다.In addition, examples of the organic electroluminescent compound of Chemical Formula 4 include the following Chemical Formulas 28 to 31.

Figure pat00019
Figure pat00019

Figure pat00020
Figure pat00020

상기 화학식 28 내지 31에서,In Chemical Formulas 28 to 31,

Ar1 , Ar2 , X3 및 Y는 상기 화학식 4에서의 정의와 동일하다.
Ar 1 , Ar 2 , X 3 and Y are the same as defined in the formula (4).

본 발명의 유기 전계 발광 화합물의 구체예는 다음과 같으나, 본 발명이 이들 화합물로 한정되는 것은 아니다. Specific examples of the organic electroluminescent compound of the present invention are as follows, but the present invention is not limited to these compounds.

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

Figure pat00025
Figure pat00025

Figure pat00026
Figure pat00026

Figure pat00027
Figure pat00027

Figure pat00028
Figure pat00028

Figure pat00029
Figure pat00029

Figure pat00030
Figure pat00030

Figure pat00031
Figure pat00031

Figure pat00032
Figure pat00032

Figure pat00033
Figure pat00033

Figure pat00034
Figure pat00034

Figure pat00035
Figure pat00035

Figure pat00036
Figure pat00036

Figure pat00037
Figure pat00037

Figure pat00038
Figure pat00038

Figure pat00039
Figure pat00039

Figure pat00040
Figure pat00040

Figure pat00041
Figure pat00041

Figure pat00042
Figure pat00042

Figure pat00043
Figure pat00043

본 발명의 상기 화합물들은 당업계에 공지된 합성 방법에 의해 제조할 수 있다. 예를 들어, 스즈키(Suzuki) 반응 등을 이용할 수 있다.The compounds of the present invention can be prepared by synthetic methods known in the art. For example, a Suzuki reaction can be used.

본 발명의 다른 양태에 따르면, 본 발명은 상기 유기 전계 발광 화합물을 포함하는 유기 전계 발광 소자를 제공한다.According to another aspect of the present invention, the present invention provides an organic electroluminescent device comprising the organic electroluminescent compound.

상기 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가진다.The organic electroluminescent device includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode.

상기 제1전극과 제2전극 중 하나는 애노드이고 다른 하나는 캐소드일 수 있다. 상기 유기물층은 발광층을 포함하고, 정공주입층, 정공수송층, 전자수송층, 전자주입층, 및 계면층(interlayer) 및 정공차단층에서 선택되는 1층 이상을 더 포함할 수 있다.One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic layer may include a light emitting layer, and may further include one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and an interlayer and a hole blocking layer.

상기 애노드용 물질로서는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화주석(SnO2), 산화아연(ZnO) 등이 사용될 수 있고, 상기 캐소드용 물질로는 일 함수(work function)가 작은 리튬, 마그네슘, 칼슘, 알루미늄, Al:Li, Ba:Li 또는 Ca:Li 등이 사용될 수 있다.As the anode material, indium tin oxide (ITO), tin oxide (SnO 2 ), zinc oxide (ZnO), or the like, which is transparent and has excellent conductivity, may be used, and as the material for the cathode, lithium having a small work function is used. , Magnesium, calcium, aluminum, Al: Li, Ba: Li, or Ca: Li may be used.

상기 유기물층, 바람직하게는 발광층은 본 발명의 상기 화학식 I의 화합물을 하나 이상 포함하고, 이 발광층에서 상기 화학식 I의 화합물을 호스트 물질로 사용할 수 있다. 또한, 바람직하게는, 상기 발광층은 하나 이상의 인광 도펀트를 더 포함한다. 필요한 경우, 상기 화학식 I의 화합물 이외의 다른 공지의 발광 화합물을 하나 이상 더 포함할 수도 있다.The organic layer, preferably the light emitting layer, includes at least one compound of formula (I) of the present invention, and the compound of formula (I) may be used as a host material in the light emitting layer. Also, preferably, the light emitting layer further includes one or more phosphorescent dopants. If necessary, one or more other light emitting compounds other than the compound of the formula (I) may be further included.

본 발명의 유기 전계 발광 소자에 사용되는 도펀트는 특별히 제한되지는 않으나, 바람직하게는 인광 도펀트이다. 인광 도펀트로는 구리, 루테늄, 로듐, 팔라듐, 은, 레늄, 오스뮴, 이리듐, 백금 또는 금을 포함하는 화합물이 있고, 구리 착체, 오스뮴 착체, 이리듐 착체, 백금 착체 등의 금속 착체인 것이 바람직하며, 그 중에서도 이리듐 착체 및 백금 착체가 더 바람직하고, 오르토 금속화 이리듐 착체가 더더욱 바람직하다. 하기 화합물 D-1 내지 D-28로 예시될 수 있다.The dopant used in the organic electroluminescent device of the present invention is not particularly limited, but is preferably a phosphorescent dopant. Phosphorescent dopants include compounds containing copper, ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum or gold, preferably metal complexes such as copper complexes, osmium complexes, iridium complexes, platinum complexes, Among them, the iridium complex and the platinum complex are more preferable, and the ortho metallized iridium complex is even more preferable. It can be illustrated by the following compounds D-1 to D-28.

Figure pat00044
Figure pat00044

본 발명의 상기 유기 전계 발광 소자는 상기 화학식 I의 화합물을 포함하는 상기 유기물층에 추가하여, 청색, 적색 또는 녹색 발광 화합물을 포함하는 발광층 하나 이상을 더 포함함으로써 전체적으로 백색 발광을 할 수 있다.  상기 청색, 적색 또는 녹색 발광 화합물은 당업계에 공지되어 있다. 또는 필요에 따라 황색 또는 오렌지색 발광층을 더 포함할 수 있다.The organic electroluminescent device of the present invention is in addition to the organic material layer containing the compound of formula (I), White light may be generated as a whole by further including at least one light emitting layer including a blue, red or green light emitting compound. Such blue, red or green light emitting compounds are known in the art. Or it may further comprise a yellow or orange light emitting layer as needed.

또한, 본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도펀트의 혼합 영역 또는 정공 전달 화합물과 산화성 도펀트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도펀트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도펀트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도펀트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.Moreover, in the organic electroluminescent element of this invention, it is also preferable to arrange | position the mixed region of an electron transfer compound and a reducing dopant, or the mixed region of a hole transfer compound and an oxidative dopant on at least one surface of a pair of electrodes. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Further, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reductive dopant layer as a charge generation layer.

본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as &quot; surface layer &quot;) is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO X (1? X ? 2), AlO x (1? X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.

또한, 본 발명은 유기 전계 발광 소자용 조성물을 제공하며, 제1호스트 재료 및 제2호스트 재료를 포함하며, 상기 제1호스트 재료는 본 발명의 유기 전계 발광 화합물을 사용한다. 이 때 제1 호스트 재료와 제 2호스트 재료의 중량비는 1:99 내지 99:1 범위 내인 것이 바람직하다.The present invention also provides a composition for an organic electroluminescent device, comprising a first host material and a second host material, wherein the first host material uses the organic electroluminescent compound of the present invention. At this time, the weight ratio of the first host material and the second host material is preferably in the range of 1:99 to 99: 1.

이하에서는 본 발명의 구체적인 실시예들을 제시한다. 다만, 하기 실시예들은 본 발명을 구체적으로 예시하거나 설명하기 위한 것에 불과하고, 본 발명이 이들로 한정되는 것은 아니다. Hereinafter, specific embodiments of the present invention will be described. However, the following examples are merely for illustrating or explaining the present invention in detail, and the present invention is not limited thereto.

하기 실시예에서 사용된 약자의 의미는 다음과 같다. The meanings of the abbreviations used in the following examples are as follows.

EtOH: 에탄올,  DMF: 디메틸포름아미드, EDA: 에틸렌디아민EtOH: ethanol, DMF: dimethylformamide, EDA: ethylenediamine

EA: 에틸아세테이트, MC:메틸렌클로라이드, THF:테트라하이드로푸란EA: ethyl acetate, MC: methylene chloride, THF: tetrahydrofuran

Tol:톨루엔, rt: 실온Tol: toluene, rt: room temperature

[제조 [Produce 실시예Example ]]

제조 Produce 실시예Example 1: 화합물 42의 제조 1: Preparation of Compound 42

Figure pat00045
Figure pat00045

화합물 42-3의 합성Synthesis of Compound 42-3

화합물 42-1 (14g, 48.76mmol), 화합물 42-2 (10g, 40.63mmol), K2CO3 (13.5g, 97.52mmol) 및 Pd(PPh3)4 (2.35g, 2.03mmol)을 톨루엔 200㎖, EtOH 50㎖ 및 정제수 50㎖의 혼합물에 투입한 후 90~100℃에서 3시간 동안 교반하였다. 반응 종결 후 실온으로 냉각한 뒤 정치하여 유기상/수상의 2상 혼합물을 수득하였다. 수상을 제거하고, 유기상은 농축 후 컬럼 크로마토그래피로 분리하여 화합물 42-3 (12g, 72%)을 수득하였다.Compound 42-1 (14g, 48.76mmol), Compound 42-2 (10g, 40.63mmol), K 2 CO 3 (13.5g, 97.52mmol) and Pd (PPh 3 ) 4 (2.35g, 2.03mmol) toluene 200 After adding to a mixture of ㎖, EtOH 50ml and 50ml purified water and stirred at 90 ~ 100 ℃ for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and then left to obtain a biphasic mixture of an organic phase / aqueous phase. The aqueous phase was removed and the organic phase was concentrated and separated by column chromatography to give compound 42-3 (12 g, 72%).

Figure pat00046
Figure pat00046

화합물 42-5의 합성Synthesis of Compound 42-5

화합물 42-3 (20 g, 49 mmol)과 화합물 42-4 (15.6 g, 73.6 mmol)을 DMF 500 ㎖에 현탁한 뒤 60% NaH (2.4 g, 58.8 mmol)를 실온에서 투입하였다. 12시간 동안 교반하였다. 유기상을 EA로 추출한 후 감압하여 농축하였다. 농축액을 컬럼 크로마토그래피로 분리하여 화합물 42-5 (21 g, 76%)를 수득하였다.Compound 42-3 (20 g, 49 mmol) and Compound 42-4 (15.6 g, 73.6 mmol) were suspended in 500 mL of DMF, followed by addition of 60% NaH (2.4 g, 58.8 mmol) at room temperature. Stir for 12 hours. The organic phase was extracted with EA and then concentrated under reduced pressure. The concentrate was separated by column chromatography to give compound 42-5 (21 g, 76%).

Figure pat00047
Figure pat00047

화합물 42의 합성Synthesis of Compound 42

화합물 42-5 (20 g, 35 mmol), 화합물 42-6 (8.3 g, 42 mmol), K2CO3 (14.5 g, 105 mmol) 및 Pd(PPh3)4 (2.02 g, 1.75 mmol)을 톨루엔 200 ㎖, EtOH 40 ㎖ 및 정제수 40 ㎖의 혼합물에 투입한 후 90~100℃에서 3시간 동안 교반하였다. 반응 종결 후 실온으로 냉각한 뒤 정치하여 유기상/수상의 2상 혼합물을 수득하였다. 수상을 제거하고, 유기상을 농축 후 컬럼 크로마토그래피로 분리하여 화합물 42 (16.4 g, 68%)를 수득하였다.
Compound 42-5 (20 g, 35 mmol), Compound 42-6 (8.3 g, 42 mmol), K 2 CO 3 (14.5 g, 105 mmol) and Pd (PPh 3 ) 4 (2.02 g, 1.75 mmol) The mixture was added to a mixture of 200 ml of toluene, 40 ml of EtOH, and 40 ml of purified water, followed by stirring at 90˜100 ° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and then left to obtain a biphasic mixture of an organic phase / aqueous phase. The aqueous phase was removed and the organic phase was concentrated and then separated by column chromatography to give compound 42 (16.4 g, 68%).

제조 Produce 실시예Example 2: 화합물 43의 제조  2: Preparation of Compound 43

Figure pat00048
Figure pat00048

화합물 43-4의 합성Synthesis of Compound 43-4

화합물 43-3(14g, 34.3mmol)과 1-브로모-4-아이오도벤젠(48.5g, 171.4mmol), CuI(3.3 g, 17.1mmol), K3PO4(21.8 g, 102.9 mmol) 및 EDA(2.3 ㎖, 34.3 mmol)를 톨루엔 500㎖ 에 투입 후 하루 동안 환류 교반하였다. 유기상을 EA로 추출한 후 감압증류하고 MC/헥산으로 컬럼 크로마토그래피로 분리하여 화합물 43-4 (15.5 g, 80.1 %)를 수득하였다.Compound 43-3 (14 g, 34.3 mmol) and 1-bromo-4-iodobenzene (48.5 g, 171.4 mmol), CuI (3.3 g, 17.1 mmol), K 3 PO 4 (21.8 g, 102.9 mmol) and EDA (2.3 mL, 34.3 mmol) was added to 500 mL of toluene and stirred at reflux for one day. The organic phase was extracted with EA, distilled under reduced pressure and separated by column chromatography with MC / hexane to give compound 43-4 (15.5 g, 80.1%).

Figure pat00049
Figure pat00049

화합물 43-5의 합성Synthesis of Compound 43-5

화합물 43-4(15.5g, 27.5mmol)을 THF(250㎖)에 녹이고 -78℃에서 헥산 중 2.5 M n-BuLi (17.6 ㎖, 44 mmol)을 첨가한 후 한 시간 동안 교반하였다. B(OMe)3(12.6㎖, 55 mmol)을 천천히 첨가하여 2시간 동안 교반하였다. 2M HCl을 첨가하여 켄칭(quenching)한 후 유기상을 증류수와 EA로 추출하였다. MC와 헥산으로 재결정하여 화합물 43-5 (8.7g, 60 %)를 수득하였다.Compound 43-4 (15.5 g, 27.5 mmol) was dissolved in THF (250 mL) and 2.5 M n-BuLi (17.6 mL, 44 mmol) in hexane was added at −78 ° C. and stirred for an hour. B (OMe) 3 (12.6 mL, 55 mmol) was added slowly and stirred for 2 hours. After quenching with the addition of 2M HCl, the organic phase was extracted with distilled water and EA. Recrystallization with MC and hexanes gave compound 43-5 (8.7 g, 60%).

Figure pat00050
Figure pat00050

화합물 43-7의 합성Synthesis of Compound 43-7

화합물 43-5 (9.5 g, 18 mmol), 화합물 43-6 (7.6 g, 36 mmol), Pd(PPh3)4 (994 mg, 0.86 mmol) 및 Na2CO3 (4.8 g, 45.3 mmol)을 톨루엔 100 ㎖, EtOH 20 ㎖ 및 증류수 20 ㎖ 의 혼합물에 녹인 후 90℃로 2시간 동안 교반하였다. 유기상을 증류수와 EA로 추출한 후 MC와 헥산으로 컬럼 크로마토그래피로 분리하여 화합물 43-7 (10 g, 85 %)을 수득하였다.Compound 43-5 (9.5 g, 18 mmol), Compound 43-6 (7.6 g, 36 mmol), Pd (PPh 3 ) 4 (994 mg, 0.86 mmol) and Na 2 CO 3 (4.8 g, 45.3 mmol) After dissolving in a mixture of 100 ml of toluene, 20 ml of EtOH, and 20 ml of distilled water, the mixture was stirred at 90 ° C. for 2 hours. The organic phase was extracted with distilled water and EA and then separated by column chromatography with MC and hexane to give compound 43-7 (10 g, 85%).

Figure pat00051
Figure pat00051

화합물 43의 합성Synthesis of Compound 43

화합물 43-7 (10 g, 15.45 mmol), 화합물 43-8 (4.5 g, 21.2 mmol), Pd(PPh3)4 (890 mg, 0.77 mmol) 및 K2CO3 (6.4 g, 46.35 mmol)을 톨루엔 80 ㎖, EtOH 10 ㎖ 및 증류수 10 ㎖ 의 혼합물에 녹인 후 90 ℃로 2시간 동안 교반하였다. 유기상을 증류수와 EA로 추출한 후 MC와 헥산으로 컬럼 크로마토그래피로 분리하여 화합물 43 (7.45 g, 62 %)을 수득하였다.
Compound 43-7 (10 g, 15.45 mmol), Compound 43-8 (4.5 g, 21.2 mmol), Pd (PPh 3 ) 4 (890 mg, 0.77 mmol) and K 2 CO 3 (6.4 g, 46.35 mmol) After dissolving in a mixture of 80 ml of toluene, 10 ml of EtOH, and 10 ml of distilled water, the mixture was stirred at 90 ° C. for 2 hours. The organic phase was extracted with distilled water and EA and then separated by column chromatography with MC and hexane to give compound 43 (7.45 g, 62%).

제조 Produce 실시예Example 3: 화합물 40의 제조 3: Preparation of Compound 40

Figure pat00052
Figure pat00052

화합물 40의 합성Synthesis of Compound 40

화합물 40-5 (20 g, 35 mmol), 화합물 40-6 (9.6 g, 42 mmol), K2CO3 (14.5 g, 105 mmol) 및 Pd(PPh3)4 (2.02 g, 1.75 mmol)을 톨루엔 200 ㎖, EtOH 40 ㎖ 및 정제수 40 ㎖ 의 혼합물에 투입 후 90~100℃에서 3시간 동안 교반 하였다. 반응 종결 후 실온으로 냉각한 뒤 정치하여 유기상/수상의 2상 혼합물을 수득하였다. 수상을 제거하고, 유기상을 농축 후 컬럼 크로마토그래피로 분리하여 화합물 40 (16.8 g, 67%)을 수득하였다.
Compound 40-5 (20 g, 35 mmol), compound 40-6 (9.6 g, 42 mmol), K 2 CO 3 (14.5 g, 105 mmol) and Pd (PPh 3 ) 4 (2.02 g, 1.75 mmol) The mixture was added to a mixture of 200 ml of toluene, 40 ml of EtOH, and 40 ml of purified water, followed by stirring at 90˜100 ° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and then left to obtain a biphasic mixture of an organic phase / aqueous phase. The aqueous phase was removed and the organic phase was concentrated and then separated by column chromatography to give compound 40 (16.8 g, 67%).

제조 Produce 실시예Example 4: 화합물 95의 제조  4: Preparation of Compound 95

Figure pat00053
Figure pat00053

화합물 95-3의 합성Synthesis of Compound 95-3

화합물 95-1 (127g, 0.60mol), 화합물 95-2 (100g, 0.50mol), K2CO3 (159g, 1.50mol) 및 Pd(PPh3)4 29g(0.03mol)을 톨루엔 3L, EtOH 750㎖ 및 정제수 750㎖ 의 혼합물에 투입한 후 하루 동안 환류 교반하였다. 생성된 유기상을 에틸아세테이트 2 ℓ로 추출한 후, 증류수 500 ㎖로 세척하였다. 유기상을 무수황산마그네슘으로 건조하고, 유기용매는 감압 하에서 제거하였다. 얻어진 고체를 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 95-3 (126g, 87%)을 수득하였다.Compound 95-1 (127g, 0.60mol), Compound 95-2 (100g, 0.50mol), K 2 CO 3 (159g, 1.50mol) and Pd (PPh 3 ) 4 29g (0.03mol) were added to toluene 3L, EtOH 750 The mixture was added to a mixture of 750 ml and purified water, followed by stirring under reflux for one day. The resulting organic phase was extracted with 2 L of ethyl acetate and washed with 500 ml of distilled water. The organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure. The obtained solid was separated by silica gel column chromatography and recrystallization to give compound 95-3 (126g, 87%).

Figure pat00054
Figure pat00054

화합물 95-4의 합성Synthesis of Compound 95-4

화합물 95-3 (126g, 0.44mol)을 트리에틸포스파이트 1.1 ℓ에 녹이고 150℃로 환류 교반하였다. 5시간 후 상온으로 냉각하고 감압 증류하였다. 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 95-4 (80g, 71%)을 수득하였다.Compound 95-3 (126 g, 0.44 mol) was dissolved in 1.1 L of triethylphosphite and stirred under reflux at 150 ° C. After 5 hours, the reaction mixture was cooled to room temperature and distilled under reduced pressure. Silica gel column chromatography and recrystallization to give the compound 95-4 (80g, 71%).

Figure pat00055
Figure pat00055

화합물 95-6의 합성Synthesis of Compound 95-6

화합물 95-4 (10g, 38.87mmol)를 DMF 200㎖에 녹인 후, NaH 2.3g(58.30mmol)을 천천히 넣어준다. 30분 동안 교반한 후 화합물 95-5 (7.7g, 46.64mmol)을 첨가한 후 4시간 동안 교반한다. 이 혼합물을 증류수 800㎖에 천천히 가하여 30분 동안 교반하여 얻어진 고체를 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 95-6을 (8.7g, 53%) 수득하였다.Compound 95-4 (10 g, 38.87 mmol) was dissolved in 200 mL of DMF, and 2.3 g (58.30 mmol) of NaH was slowly added thereto. After stirring for 30 minutes, compound 95-5 (7.7 g, 46.64 mmol) is added and then stirred for 4 hours. The mixture was slowly added to 800 ml of distilled water, followed by stirring for 30 minutes. The solid obtained was separated by silica gel column chromatography and recrystallization to give compound 95-6 (8.7 g, 53%).

Figure pat00056
Figure pat00056

화합물 95의 합성Synthesis of Compound 95

화합물 95-6 (4g, 9.53mmol), 화합물 95-7 (2.2g, 11.43mmol), K2CO3 (4g, 28.59mmol) 및 Pd(PPh3)4 (0.6g, 0.48mmol)을 톨루엔 60㎖, EtOH 15㎖ 및 정제수 15㎖의 혼합물에 투입한 후 하루 동안 환류 교반하였다. 유기상을 에틸아세테이트 100㎖로 추출한 후, 증류수 50㎖로 세척하였다. 유기상을 무수황산마그네슘으로 건조하고, 유기용매는 감압하에서 제거하였다. 얻어진 고체를 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 95 (2.4g, 47%)을 수득하였다.
Compound 95-6 (4g, 9.53mmol), Compound 95-7 (2.2g, 11.43mmol), K 2 CO 3 (4g, 28.59mmol) and Pd (PPh 3 ) 4 (0.6g, 0.48mmol) toluene 60 ㎖, 15 mL of EtOH and 15 mL of purified water were added to the mixture, followed by stirring under reflux for one day. The organic phase was extracted with 100 ml of ethyl acetate and washed with 50 ml of distilled water. The organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure. The obtained solid was separated by silica gel column chromatography and recrystallization to give compound 95 (2.4 g, 47%).

제조 Produce 실시예Example 5: 화합물 96의 제조 5: Preparation of Compound 96

Figure pat00057
Figure pat00057

화합물 96-6의 합성Synthesis of Compound 96-6

화합물 95-4 (10g, 38.87mmol), 화합물 96-5 (22g, 77.74mmol), CuI (3.7g, 19.44mmol), K3PO4 (20.6g, 97.18mmol) 및 EDA (2.6㎖, 38.87mmol)을 톨루엔 200㎖에 넣고, 100℃에서 24시간 동안 교반하였다. 반응물을 실온으로 냉각한 후, 유기상을 에틸아세테이트 200㎖로 추출한 후, 증류수 50㎖로 2회 세척하였다. 유기상을 무수황산마그네슘으로 건조하고, 유기용매는 감압 하에서 제거하였다. 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 96-6 (12.3g, 77%)을 수득하였다. Compound 95-4 (10 g, 38.87 mmol), Compound 96-5 (22 g, 77.74 mmol), CuI (3.7 g, 19.44 mmol), K 3 PO 4 (20.6 g, 97.18 mmol) and EDA (2.6 mL, 38.87 mmol) ) Was added to 200 ml of toluene and stirred at 100 ° C. for 24 hours. After the reaction was cooled to room temperature, the organic phase was extracted with 200 ml of ethyl acetate and then washed twice with 50 ml of distilled water. The organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure. Silica gel column chromatography and recrystallization to give the compound 96-6 (12.3g, 77%).

Figure pat00058
Figure pat00058

화합물 96-7의 합성Synthesis of Compound 96-7

화합물 96-6 (12.3g, 29.83mmol)을 THF 150㎖에 녹인 후 n-BuLi (헥산 중 2.5 M) 17.9㎖(44.75mmol)를 -78℃에서 첨가하였다. 이 혼합물을 -78℃에서 1시간 동안 교반한 후 B(Oi-Pr)3 화합물을 (10.3㎖, 44.75mmol) 첨가하였다. 전체 반응물을 2시간 동안 교반한 후 NH4Cl 100㎖로 반응을 종결시키고, 유기상을 에틸아세테이트 200㎖로 추출한 후, 증류수 100 ㎖로 세척하였다. 유기상을 MgSO4로 건조하고, 유기용매는 감압 하에서 제거하였다. 얻어진 고체를 재결정방법으로 분리하여 화합물 96-7 (8.2g, 73%)을 수득하였다.Compound 96-6 (12.3 g, 29.83 mmol) was dissolved in 150 mL of THF, and then 17.9 mL (44.75 mmol) of n-BuLi (2.5 M in hexane) was added at -78 ° C. The mixture was stirred at −78 ° C. for 1 hour before the addition of B (Oi-Pr) 3 compound (10.3 mL, 44.75 mmol). After stirring the whole reaction for 2 hours, the reaction was terminated with 100 mL of NH 4 Cl, and the organic phase was extracted with 200 mL of ethyl acetate, and then washed with 100 mL of distilled water. The organic phase was dried over MgSO 4 and the organic solvent was removed under reduced pressure. The obtained solid was separated by recrystallization to give compound 96-7 (8.2 g, 73%).

Figure pat00059
Figure pat00059

화합물 96-9의 합성Synthesis of Compound 96-9

화합물 96-7 (8.2g, 21.62mmol), 화합물 96-8 (3.9g, 19.66mmol), Na2CO3 (5.2g. 49.15mmol) 및 Pd(PPh3)4 (1.2g, 0.98mmol)을 톨루엔 100㎖, EtOH 25㎖ 및 정제수 25㎖의 혼합물에 투입한 후 하루 동안 환류 교반하였다. 유기상을 에틸아세테이트 100㎖로 추출한 후, 증류수 50㎖로 세척하였다. 유기상을 무수황산마그네슘으로 건조하고, 유기용매는 감압 하에서 제거하였다. 얻어진 고체를 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 96-9 (4g, 41%)을 수득하였다.Compound 96-7 (8.2 g, 21.62 mmol), Compound 96-8 (3.9 g, 19.66 mmol), Na 2 CO 3 (5.2 g. 49.15 mmol) and Pd (PPh 3 ) 4 (1.2 g, 0.98 mmol) The mixture was added to a mixture of 100 ml of toluene, 25 ml of EtOH, and 25 ml of purified water, followed by stirring under reflux for one day. The organic phase was extracted with 100 ml of ethyl acetate and washed with 50 ml of distilled water. The organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure. The obtained solid was separated by silica gel column chromatography and recrystallization to give compound 96-9 (4g, 41%).

Figure pat00060
Figure pat00060

화합물 96의 합성Synthesis of Compound 96

화합물 96-9 (4g, 8.07mmol), 화합물 96-10 (1.8g, 9.68mmol), K2CO3 (3.4g, 24.20mmol) 및 Pd(PPh3)4 (0.5g, 0.41mmol)을 톨루엔 60㎖, EtOH 15㎖ 및 정제수 15㎖의 혼합물에 투입한 후 하루 동안 환류 교반하였다. 유기상을 에틸아세테이트 100㎖로 추출한 후, 증류수 50㎖로 세척하였다. 유기상을 무수황산마그네슘으로 건조하고, 유기용매는 감압 하에서 제거하였다. 얻어진 고체는 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 96 (1.2g, 24%)을 수득하였다.
Compound 96-9 (4g, 8.07mmol), Compound 96-10 (1.8g, 9.68mmol), K 2 CO 3 (3.4g, 24.20mmol) and Pd (PPh 3 ) 4 (0.5g, 0.41mmol) toluene 60 ml, 15 ml of EtOH and 15 ml of purified water were added to the mixture, followed by stirring under reflux for one day. The organic phase was extracted with 100 ml of ethyl acetate and washed with 50 ml of distilled water. The organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed under reduced pressure. The obtained solid was separated by silica gel column chromatography and recrystallization to give compound 96 (1.2g, 24%).

상기 제조 실시예 1 내지 5에서 제조한 최종 화합물의 물성 데이터는 다음과 같다. Physical properties data of the final compound prepared in Preparation Examples 1 to 5 are as follows.

Figure pat00061
Figure pat00061

[[ 실시예Example 1] 본 발명에 따른 유기  1] The organic 전계Field 발광 화합물을 이용한  Using a luminescent compound OLEDOLED 소자 제작 Device fabrication

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 제조된 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올 및 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO 기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-바이페닐]-4,4'-다이일)비스(N1-(나프탈렌-1-일)-N4,N4-다이페닐벤젠-1,4-다이아민)을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-다이(4-바이페닐)-N,N'-다이(4-바이페닐)-4,4'-다이아미노바이페닐을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 화합물 42를 넣고, 또 다른 셀에는 도펀트로서 화합물 D-7을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 두 물질의 합이 4 중량%가 되도록 도핑함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 2-(4-(9,10-다이(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸을 넣고, 또 다른 셀에는 리튬 퀴놀레이트를 각각 넣은 후, 두 물질을 같은 속도로 증발시켜 두 물질의 합이 50 중량%가 되도록 도핑함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로  리튬 퀴놀레이트를 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (15Ω / □) manufactured from OLED glass (manufactured by Samsung-Corning) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol, and distilled water sequentially, and then stored in isopropanol. It was used after. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N 1 , N 1 ′ -([1,1′-biphenyl] -4,4′-diyl) bis ( N 1-(naphthalen- 1 -yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine) was added and evacuated until the vacuum in the chamber reached 10 -6 torr. Was applied and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was placed in another cell in the vacuum deposition equipment, and the current was put into the cell. Was applied and evaporated to deposit a 20 nm thick hole transport layer on the hole injection layer. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. Compound 42 as a host in one cell in the vacuum deposition equipment, Compound D-7 as a dopant in each cell, and then the two materials were evaporated at different rates to dope the sum of the two materials to 4% by weight. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. Then 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole in one cell as an electron transporting layer on the light emitting layer. In each cell, lithium quinolate was added to each other, and the two materials were evaporated at the same rate to be doped so that the sum of the two materials was 50% by weight, thereby depositing an electron transport layer having a thickness of 30 nm. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition equipment to fabricate an OLED device. Each compound was purified by vacuum sublimation under 10 -6 torr.

그 결과, 7.7 mA/cm2의 전류가 흘렀으며, 1335cd/m2의 적색발광이 확인되었다.As a result, a current of 7.7 mA / cm 2 flowed, and red light emission of 1335 cd / m 2 was confirmed.

[[ 실시예Example 2] 본 발명에 따른 유기발광화합물을 이용한  2] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication

발광재료로서 호스트에는 화합물 95, 도펀트에는 화합물 D-7을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 95 was used as a light emitting material and Compound D-7 was used as a dopant.

그 결과, 8.6 mA/cm2의 전류가 흘렀으며, 1554cd/m2의 적색발광이 확인되었다.As a result, a current of 8.6 mA / cm 2 flowed, and red light emission of 1554 cd / m 2 was confirmed.

[[ 실시예Example 3] 본 발명에 따른 유기발광화합물을 이용한  3] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication

발광재료로서 호스트에는 화합물 96, 도펀트에는 화합물 D-11을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 96 was used as a light emitting material and Compound D-11 was used as a dopant.

그 결과, 15.0 mA/cm2의 전류가 흘렀으며, 1290cd/m2의 적색발광이 확인되었다.As a result, a current of 15.0 mA / cm 2 flowed, and red light emission of 1290 cd / m 2 was confirmed.

[[ 비교예Comparative Example 1] 종래의 발광재료를 이용한  1] using conventional light emitting material OLEDOLED 소자 제작 Device fabrication

발광재료로서 호스트에는 4,4'-N,N'-디카바졸-바이페닐, 도펀트로는 화합물 D-11을 사용하고, 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 알루미늄(III)비스(2-메틸-8-퀴놀리나토)4-페닐페놀레이트를 10nm 두께로 증착한 것 외에는 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다.As a light emitting material, 4,4'-N, N'-dicarbazole-biphenyl is used as a host, and compound D-11 is used as a dopant, and a light emitting layer having a thickness of 30 nm is deposited on the hole transport layer, and aluminum is used as the hole blocking layer. III) An OLED device was manufactured in the same manner as in Example 1, except that bis (2-methyl-8-quinolinato) 4-phenylphenolate was deposited to a thickness of 10 nm.

그 결과, 20.0 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 적색발광이 확인되었다.As a result, a current of 20.0 mA / cm 2 flowed, and red light emission of 1000 cd / m 2 was confirmed.

본 발명에서 개발한 유기발광 화합물들은 적색발광 재료로서 종래의 발광재료 대비 우수한 발광특성을 보이는 것을 확인할 수 있었다. 종래의 소자구조에서 정공차단층을 사용하지 않고도 본 발명에 따른 유기 전계 발광 화합물을 호스트재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 전력효율상승을 유도할 수 있었다. The organic light emitting compounds developed in the present invention can be seen that the red light emitting material shows excellent light emission characteristics compared to the conventional light emitting material. In the conventional device structure, the device using the organic electroluminescent compound according to the present invention as a host material without using a hole blocking layer is excellent in light emission characteristics and can lead to an increase in power efficiency.

Claims (4)

하기 화학식 1 내지 4 중 어느 하나로 표시되는 유기 전계 발광 화합물.
[화학식 1]
Figure pat00062

[화학식 2]
Figure pat00063

[화학식 3]
Figure pat00064

[화학식 4]
Figure pat00065

상기 화학식 1 내지 4에서,
X1 및 X2는 각각 독립적으로 CR0 또는 N이며, X1 및 X2 중 하나 이상은 N이고;
Ar1, Ar2 및 Ar3은 각각 독립적으로 수소, 치환 또는 비치환된 C6-C30 아릴 그룹, 또는 치환 또는 비치환된 5-60원 헤테로아릴 그룹이고;
L1, L2 및 L3은 각각 독립적으로 단일결합이거나 치환 또는 비치환된 C6 -C30 아릴렌이고;
A, B, C 및 D 환은 각각 독립적으로 치환 또는 비치환된 C6-C30 방향족 환 또는 치환 또는 비치환된 5-60원 방향족 헤테로환이고, 이 때 상기 A 및 D 환에 대한 치환체 중 하나 이상은 인접한 치환체와 함께 융합된 환을 형성할 수 있으며;
E는 하기 화학식 5의 구조를 가지며, 하기 화학식 5에서, F 및 G 환은 각각 독립적으로 치환 또는 비치환된 C6-C30 방향족 환 또는 치환 또는 비치환된 5-60원 방향족 헤테로환이고, 이 때 상기 환들에 대한 치환체 중 하나 이상은 인접한 치환체와 함께 융합된 환을 형성할 수 있으며, Z는 단일 결합이고, q는 0 또는 1이며;
[화학식 5]
Figure pat00066

X3, X 및 Y는 각각 독립적으로 NR1, CR2R3, O 또는 S이고;
R0, R1, R2 및 R3는 각각 독립적으로, 수소, 치환 또는 비치환된 C1-C30 알킬, 치환 또는 비치환된 C6-C30 아릴, 또는 치환 또는 비치환된 5-60원 헤테로아릴이고;
m, n, o 및 p는 각각 독립적으로 0 또는 1이며, n+o+p는 1 이상이고;
단, 상기 화학식 1 내지 4에서 하기 화합물은 제외된다.
Figure pat00067
An organic electroluminescent compound represented by any one of the following Chemical Formulas 1 to 4.
[Formula 1]
Figure pat00062

(2)
Figure pat00063

(3)
Figure pat00064

[Formula 4]
Figure pat00065

In the above Chemical Formulas 1 to 4,
XOne And X2Are each independently CR0 Or N, XOne And X2 At least one of is N;
ArOne, Ar2 And Ar3Are each independently hydrogen, substituted or unsubstituted C6-C30 Aryl group or substituted or unsubstituted 5-60 membered heteroaryl group;
LOne, L2 And L3Are each independently a single bond, substituted or unsubstituted C6 -C30 Arylene;
A, B, C and D ring are each independently substituted or unsubstituted C6-C30 An aromatic ring or a substituted or unsubstituted 5-60 membered aromatic heterocycle, wherein at least one of the substituents for the A and D rings may form a fused ring with adjacent substituents;
E has a structure of Formula 5, wherein in Formula 5, F and G ring are each independently substituted or unsubstituted C6-C30 An aromatic ring or a substituted or unsubstituted 5-60 membered aromatic heterocycle, wherein at least one of the substituents for the rings may form a fused ring with adjacent substituents, Z is a single bond, q is 0 Or 1;
[Chemical Formula 5]
Figure pat00066

X3, X and Y are each independently NROne, CR2R3, O or S;
R0, ROne, R2 And R3Are each independently hydrogen, substituted or unsubstituted COne-C30 Alkyl, substituted or unsubstituted C6-C30 Aryl or substituted or unsubstituted 5-60 membered heteroaryl;
m, n, o and p are each independently 0 or 1 and n + o + p is 1 or more;
However, in the above Chemical Formulas 1 to 4, the following compounds are excluded.
Figure pat00067
제1항에 있어서,
m=1, n=1, o=0, p=0이고, L2는 단일결합인 유기 전계 발광 화합물;
m=0, n=1, o=1 및 p=0인 유기 전계 발광 화합물;
m=0, n=1, o=0 및 p=1인 유기 전계 발광 화합물;
m=0, n=0, o=0 및 p=1인 유기 전계 발광 화합물; 및
m=1, n=1, o=0, p=1이고, L2는 단일결합인 유기 전계 발광 화합물
로 이루어진 군으로부터 선택되는 것인 유기 전계 발광 화합물. 
The method of claim 1,
m = 1, n = 1, o = 0, p = 0, L 2 is a single bond organic electroluminescent compound ;
organic electroluminescent compounds with m = 0, n = 1, o = 1 and p = 0;
organic electroluminescent compounds with m = 0, n = 1, o = 0 and p = 1;
organic electroluminescent compounds with m = 0, n = 0, o = 0 and p = 1; And
an organic electroluminescent compound having m = 1, n = 1, o = 0, p = 1 and L 2 is a single bond
An organic electroluminescent compound selected from the group consisting of.
제1항에 있어서, 하기 화합물들로부터 선택되는 것인 유기 전계 발광 화합물.
Figure pat00068

Figure pat00069

Figure pat00070

Figure pat00071

Figure pat00072

Figure pat00073

Figure pat00074

Figure pat00075

Figure pat00076

Figure pat00077

Figure pat00078

Figure pat00079

Figure pat00080

Figure pat00081

Figure pat00082

Figure pat00083

Figure pat00084

Figure pat00085

Figure pat00086

Figure pat00087

Figure pat00088

Figure pat00089

Figure pat00090
The organic electroluminescent compound according to claim 1, which is selected from the following compounds.
Figure pat00068

Figure pat00069

Figure pat00070

Figure pat00071

Figure pat00072

Figure pat00073

Figure pat00074

Figure pat00075

Figure pat00076

Figure pat00077

Figure pat00078

Figure pat00079

Figure pat00080

Figure pat00081

Figure pat00082

Figure pat00083

Figure pat00084

Figure pat00085

Figure pat00086

Figure pat00087

Figure pat00088

Figure pat00089

Figure pat00090
제1항에 따른 유기 전계 발광 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
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