KR101561340B1 - 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 - Google Patents
유기 화합물 및 이를 포함하는 유기 전계 발광 소자 Download PDFInfo
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- KR101561340B1 KR101561340B1 KR1020130082870A KR20130082870A KR101561340B1 KR 101561340 B1 KR101561340 B1 KR 101561340B1 KR 1020130082870 A KR1020130082870 A KR 1020130082870A KR 20130082870 A KR20130082870 A KR 20130082870A KR 101561340 B1 KR101561340 B1 KR 101561340B1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- Physics & Mathematics (AREA)
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
계산값 B3LYP/6-31G* | ||||||||||
PGH | 구조 | HOMO | LUMO | Bandgap | S1 | T1 | S1-T1 | Dipole moment(Debye) | Total energy | F value |
HT_TM01 | -4.774 | -1.020 | 3.753 | 3.189 | 3.005 | 0.182 | 2.4907 | -2320 | 0.0047 0.1556 0.0012 |
|
HT_TM02 | -4.660 | -0.986 | 3.674 | 3.223 | 3.001 | 0.222 | 0.8800 | -2680 | 0.0029 0.0835 0.0005 |
|
HT_TM03 | -4.793 | -0.984 | 3.809 | 3.187 | 2.815 | 0.373 | 1.4706 | -2400 | 0.0084 0.0747 0.0012 |
발광 재료 | 구동 전압(V) | 발광 피크(nm) | 전류효율(cd/A) | |
실시예 1 | C 1 | 6.90 | 521 | 42.1 |
실시예 2 | C 2 | 6.85 | 521 | 42.0 |
실시예 3 | C 3 | 6.80 | 520 | 42.1 |
실시예 4 | C 4 | 6.95 | 520 | 42.0 |
실시예 5 | C 5 | 6.98 | 520 | 41.8 |
실시예 6 | C 16 | 6.90 | 521 | 42.0 |
실시예 7 | C 10 | 6.85 | 521 | 42.1 |
실시예 8 | C 11 | 6.85 | 521 | 41.9 |
실시예 9 | C 12 | 6.85 | 520 | 42.0 |
실시예 10 | C 13 | 6.90 | 519 | 41.9 |
실시예 11 | C 17 | 6.90 | 519 | 41.8 |
실시예 12 | C 18 | 6.85 | 519 | 42.0 |
실시예 13 | C 19 | 6.95 | 520 | 42.1 |
실시예 14 | C 20 | 6.90 | 521 | 41.9 |
실시예 15 | C 21 | 6.95 | 521 | 41.5 |
실시예 16 | C 25 | 6.95 | 521 | 41.9 |
실시예 17 | C 33 | 6.90 | 521 | 42.2 |
실시예 18 | C 34 | 6.90 | 522 | 42.1 |
실시예 19 | C 35 | 6.95 | 522 | 41.7 |
실시예 20 | C 36 | 6.90 | 522 | 42.0 |
비교예 1 | _ | 6.93 | 516 | 38.2 |
발광 재료 | 구동 전압(V) | 전류효율(cd/A) | |
실시예 21 | C 1 | 5.30 | 10.9 |
실시예 22 | C 2 | 5.20 | 10.5 |
실시예 23 | C 3 | 5.20 | 11.0 |
실시예 24 | C 4 | 5.25 | 10.6 |
실시예 25 | C 5 | 5.20 | 10.5 |
실시예 26 | C 16 | 5.30 | 11.2 |
실시예 27 | C 10 | 5.30 | 11.2 |
실시예 28 | C 11 | 5.20 | 11.0 |
실시예 29 | C 12 | 5.15 | 10.8 |
실시예 30 | C 13 | 5.15 | 10.7 |
실시예 31 | C 17 | 5.25 | 10.5 |
실시예 32 | C 18 | 5.30 | 10.8 |
실시예 33 | C 19 | 5.20 | 11.0 |
실시예 34 | C 20 | 5.20 | 11.1 |
실시예 35 | C 21 | 5.20 | 11.0 |
실시예 36 | C 25 | 5.15 | 11.2 |
실시예 37 | C 33 | 5.25 | 11.0 |
실시예 38 | C 34 | 5.30 | 10.8 |
실시예 39 | C 35 | 5.30 | 10.5 |
실시예 40 | C 36 | 5.25 | 11.0 |
비교예 1 | _ | 5.25 | 8.2 |
발광 재료 | 구동 전압(V) | 전류효율(cd/A) | |
실시예 41 | C 1 | 5.60 | 6.9 |
실시예 42 | C 2 | 5.60 | 6.8 |
실시예 43 | C 3 | 5.60 | 7.0 |
실시예 44 | C 4 | 5.55 | 6.6 |
실시예 45 | C 5 | 5.60 | 6.5 |
실시예 46 | C 16 | 5.60 | 7.2 |
실시예 47 | C 10 | 5.60 | 6.4 |
실시예 48 | C 11 | 5.50 | 7.0 |
실시예 49 | C 12 | 5.65 | 6.9 |
실시예 50 | C 13 | 5.55 | 6.7 |
실시예 51 | C 17 | 5.55 | 6.5 |
실시예 52 | C 18 | 5.60 | 6.8 |
실시예 53 | C 19 | 5.55 | 6.0 |
실시예 54 | C 20 | 5.50 | 6.1 |
실시예 55 | C 21 | 5.50 | 6.0 |
실시예 56 | C 25 | 5.65 | 6.2 |
실시예 57 | C 33 | 5.55 | 7.0 |
실시예 58 | C 34 | 5.60 | 6.8 |
실시예 59 | C 35 | 5.60 | 7.5 |
실시예 60 | C 36 | 5.55 | 7.0 |
비교예 1 | _ | 5.6 | 4.8 |
Claims (10)
- 하기 화학식 1로 표시되는 화합물:
[화학식 1]
상기 화학식 1에서,
R1과 R2, R2와 R3, 또는 R3와 R4 중 하나는 하기 화학식 2로 표시되는 축합 고리를 형성하고;
[화학식 2]
X1 및 X2는 서로 동일하거나 상이하며, 각각 독립적으로 O, S, Se, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되고, 이때 X1 및 X2 중 적어도 하나는 N(Ar1)이고;
Y1 및 Y2는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 CR11이고, 이때 CR11가 복수인 경우, 이들은 서로 동일하거나 상이하고;
R1 내지 R4중 축합 고리를 형성하지 않는 것과 R5 내지 R8 및 R11은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되고;
다만, R5 내지 R8중 적어도 하나는 하기 화학식 3으로 표시되는 치환체이며,
[화학식 3]
L은 단일 결합이거나, 혹은 치환 또는 비치환된 C6~C60의 아릴렌기, 및 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴렌기로 이루어진 군에서 선택되고;
X3 는 O, S, Se, N(Ar6), C(Ar7)(Ar8) 및 Si(Ar9)(Ar10)로 이루어진 군에서 선택되고;
R21 내지 R26 은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되거나, 또는 R21과 R22, R22와 R23, R23과 R24, R24와 R25 또는 R25와 R26는 서로 결합하여 축합방향족환 또는 축합헤테로방향족환을 형성할 수 있고;
Ar1 내지 Ar10은 서로 동일하거나 상이하며, 각각 독립적으로 1개 이상의 C6~C60의 아릴기로 치환 혹은 비치환된 C6~C60의 아릴기이고;
상기 L의 아릴렌기 및 헤테로아릴렌기와, R1 내지 R8, R11 및 R21 내지 R26 의 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되는 1종 이상의 치환기로 치환되거나 비치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. - 제1항에 있어서,
상기 화학식 3으로 표시되는 치환체는 하기 화학식 3a 내지 화학식 3h 중 어느 하나로 표시되는 치환체인 것을 특징으로 하는 화합물.
[화학식 3a]
[화학식 3b]
[화학식 c]
[화학식 3d]
[화학식 3e]
[화학식 3f]
[화학식 3g]
[화학식 3h]
상기 화학식 3a 내지 화학식 3h에서 X3 및 R21 내지 R26 은 각각 청구항 1에서 정의된 바와 같고,
R27 내지 R29 는 서로 동일하거나 상이하며, 각각 독립적으로 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C2~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되거나, 또는 R27과 R28은 서로 결합하여 축합방향족환 또는 축합헤테로방향족환을 형성할 수 있고,
n은 0내지 2의 정수에서 선택되며,
m은 0내지 5의 정수에서 선택된다. - 제1항에 있어서,
상기 X1 및 X2는 모두 N(Ar1)이고,
상기 X3은 N(Ar6)이며,
이때 복수의 N(Ar1)은 서로 동일하거나 상이한 것을 특징으로 하는 화합물. - 제1항에 있어서,
상기 R7 은 상기 화학식 3으로 표시되는 치환체이고,
상기 L은 단일 결합이며, R24 위치의 탄소에 연결되는 것을 특징으로 하는 화합물. - 제1항에 있어서,
상기 Ar1 내지 Ar10는 서로 동일하거나 상이하며, 각각 독립적으로 페닐, 바이페닐, 터페닐, 플루오레닐, 나프틸, 안트라세닐, 인덴으로 이루어진 군에서 선택될 수 있으며, 상기 페닐, 바이페닐, 터페닐, 플루오레닐, 나프틸, 안트라세닐, 인덴은 각각 독립적으로 1개 이상의 아릴기로 치환 혹은 비치환될 수 있는 것을 특징으로 하는 화합물. - 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제8항 중 어느 한 항에 기재된 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. - 제 9항에 있어서,
상기 화합물을 포함하는 1층 이상의 유기물층은 정공 수송층 및 전자 저지층으로 이루어진 군에서 선택되는 것을 특징으로 하는 유기 전계 발광 소자.
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